Labor Day Weekend is here! 🇺🇸☀️ If you’re like me, you may be sticking around town instead of heading out for one last summer getaway. But that’s one of the great things about Fairfield County—you don’t have to travel far to make the weekend feel like a mini vacation! From traditional festivals and outdoor concerts to live music, comedy, wine and great food, there’s plenty happening throughout the area. While some are heading out of town, create your own daily getaway with our curated list of things to do in and around Fairfield County this Labor Day Weekend. Let’s start in Stamford , where one of our favorite comedy spots, New York Comedy Club Stamford , has an outstanding lineup. Thursday features TJ: The Alien Everywhere Tour , followed by Damon Wayans Jr. , taking over the club Friday, Saturday and Sunday. Check the NYCC Stamford calendar for available showtimes and tickets. Looking for live music instead? Jesse McCartney hits the stage at The Palace Theatre Stamford Friday night. And while you’re out and about in Stamford, don’t forget that Stamford Restaurant Week continues through September 7! It’s the perfect excuse to try a restaurant you’ve been meaning to visit or make reservations at one of your longtime local favorites. The options are yours! 🍽️ On Saturday night, head to Edmond Town Hall for The Insiders: A Tribute to Tom Petty . At one of our favorite vineyards, Aquila’s Nest Vineyards , the weekend kicks into high gear Saturday with Dueling Pianos featuring The Flying Ivories . Then on Sunday at 6 PM, Little Lies – A Fleetwood Mac Tribute returns to the vineyard. Over in Ridgefield , head to Odeen’s Friday evening for Music on the Porch with Phil & Isabelle from 5:30–8:30 PM. Or get an early start on the weekend Thursday with Trivia Night at Odeen’s at Oak Hills —make your reservations and put your trivia skills to the test! And if you’re in a foodie mood, come hungry! 🍽️🌎 ConnectFairfield presents the 2nd Annual Fairfield International Food Festival on Saturday from 4–8 PM. Explore international flavors, enjoy the festivities and grab your tickets in advance. And this is only the beginning! Check out Fairfield After Dark’s complete Labor Day Weekend Happenings and start planning your own local getaway. Wednesday, September 2, 2026 Danbury: Wed Open Mic at Sugar Hollow Taproom(7pm) Fairfield: Music with The Lamb Jam at The Seagrape Fairfield(8:30pm) ☀️🎶New Canaan: The Short Bus Band – 70’s to Today’s Hits at Waveny Park(7:30 – 9:30pm) ⭐🎟️Newtown: Fairfield Alumni Happy Hour at Aquila's Nest Vineyards(5:30pm) ⭐🎟️Newtown: Pilates + Pour with Mia at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Reiki & Rosé at Aquila's Nest Vineyards(6pm) Norwalk: Detroy Langer & Riccio Organ Trio at Greer Southern Table(6pm - 9pm) ☀️🎶Norwalk: Funk Salsa Urban at Calf Pasture Beach(7pm) Shelton: Benny at Spotted Horse Tavern(8pm) Thursday, September 3, 2026 Bethel: FIDDLERS'S BRAWL at Whitlock’s Restaurant(6pm - 9pm) Danbury: Thursday Open Jam with Fuzz on It LIVE at Sugar Hollow Taproom(8pm) Fairfield: ETA Music at The Sinclair(8:30pm) Milford: Greg McCarthy at Cafe Atlantique(5pm) ⭐🎟️Newtown: Wine, Words & Wisdom Book Club Series at Aquila's Nest Vineyards(6:30pm) ⭐🎶Newtown: Joan Wallace at Aquila's Nest Vineyards(5:30pm) 🍔🍺🧠Norwalk: Trivia Night at ODEEN'S(7pm - 9pm) Old Greenwich: Mojo at Bosco's Bar and Grill(8:30pm) Shelton: Jack + Allie at The Gilded Whitlocks(6pm) Stratford: PAT MATTO at Blackbird's Nest(5pm) ⭐😂🎟️Stamford: Comedian TJ: The Alien Everywhere Tour at New York Comedy Club Stamford(7pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(4pm - 9:30pm) Friday, September 4, 2026 Bethel: Note To Self at Shakedown Street Eats(6:30pm) Bethel: Mystery Train at Notch8 Bar(8pm) Bethel: BRENNAN MUSIC at Whitlock’s Restaurant(6pm - 9pm) ☀️🎶Bethlehem: Hype at March Farms Hilltop (6-8pm) ☀️🎶Brookfield: DAN'S GARAGE at the Summer Concerts in the Park - Brookfield (6:30pm) ☀️🎶Bridgeport: Josh A - Friday Night Music on the Dock at Port 5(5pm –8:30pm) ☀️🎶Bridgeport: Cat Lines at Twelvenote Brew Co.(7pm - 10pm) Danbury: Roll n Roll Collective LIVE at Sugar Hollow Taproom(8:30pm) 🎪🛍️East Hampton: Haddam Neck Fair(3pm - 11pm) Milford: Tim Payson at Cafe Atlantique(6:30pm) New Milford: Lost Rebel at Housatonic River Brewing(7pm - 10pm) ⭐🎟️Newtown: Llamas and Llibations at Aquila's Nest Vineyards(5:30pm) ⭐🎟️Newtown: Baked Brie & Vino Night at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Speed Dating Ages 60+ at Aquila's Nest Vineyards(7pm) ⭐🎶Newtown: Glenn Roth at Aquila's Nest Vineyards(5:30pm - 8:30pm) Newtown: Willy Portera Trio at NewSylum Brewing Co.(6pm - 9pm) Norwalk: Pimpinella at 314 Beer Garden(7:30pm - 11pm) Norwalk: Billy G & Friends at Sails American Grill(9pm - 12am) Ridgefield: Tom Petty Night at Nod Hill Brewery(6:30pm) ⭐🍽️ 🎶Ridgefield: Isabelle & Phil on the Porch at Odeen's Ridgefield(5:30pm - 8:30pm) Sherman: Dinner & Music with Bernie Kaplan: "Yesterday and Tomorrow, Today" at JCC in Sherman(7pm - 9pm) Stratford: Brandon Mullis solo at Windmill Tavern(5pm) Stratford: TIN SANDWICH at Blackbird's Nest(6pm) Stratford: Bad Mannerz at Windmill Tavern(8pm) Stamford: Plastercade at Tiernan's Bar & Restaurant(1pm - 2pm) Stamford: Bad Saints LIVE at Third Place by Half Full Brewery(8pm - 10pm) ⭐😂🎟️Stamford: Comedian Damon Wayans Jr at New York Comedy Club Stamford (5 SHOWS!)(7pm - 9:30pm) ⭐🎟️Stamford: Jesse McCartney The Weightless Tour at The Palace Theatre Stamford(8pm) ☀️🎶Westport: Steve Ferentzy - Music on Church Lane(5:30pm –9pm) Westport: MIHALI * Full Band Show * w/ Mr Mota at Levitt Pavilion(4:30pm) Westport: Jonathan Niles Chapman at Walrus Alley(7:30pm - 10:30pm) Westport: Herman and Co. at Black Duck Cafe(9pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(12pm - 9:30pm) Saturday, September 5, 2026 Bethel: Iris Lies at Notch8 Bar(8pm) Bethel: Seth Adam LIVE at Shakedown Street Eats(6:30pm - 9:30pm) Bethel: Sound Dog LIVE at DragonFly(6pm - 9pm) Bethel: MORRIGAN’S CROSSING LIVE at Whitlock’s Restaurant(6pm - 9pm) Bridgeport: Midnight Cardinal at Captain's Cove Seaport (Marina, Restaurant & Bar)(4pm - 8pm) ☀️🎶Bridgeport: The Brother Cool Duo at Twelvenote Brew Co.(7pm - 10pm) Brookfield: Rio Sorrentino at Pulcinella(7pm - 10pm) Danbury: Danbury's Brazilian Festival(11am - 10pm) Danbury: Core. 90s and 2000s Alternative Rock LIVE at Sugar Hollow Taproom(8:30pm) 🎪🛍️East Hampton: Haddam Neck Fair(7:30pm - 11pm) 🌍🍽️ Fairfield: Fairfield International Food Festival at FTC(4pm - 8pm) 🎪🛍️Goshen: Goshen Fair(8am - 9pm) Milford: Shannon McMahon at Cafe Atlantique(6:30pm) New Milford: Street Survivors - Tribute to Lynyrd Skynyrd at Housatonic River Brewing(7pm - 10pm) ⭐🎟️Newtown: Cheesecakes & Wine Pairing at Aquila's Nest Vineyards(12pm) ⭐🎟️Newtown: Whiskers & Wine Kitten Adoption Event at Aquila's Nest Vineyards(12pm) ⭐🎟️Newtown: Dueling Pianos with the Flying Ivories at Aquila's Nest Vineyards(6pm) ⭐🎶Newtown: Red Planet(Dead/Garcia Tribute) at NewSylum Brewing Co.(3pm - 6pm) ⭐🎟️Newtown: The Insiders: Tribute to Tom Petty coming to Edmond Town Hall(8pm - 10pm) Newtown: Teacup Sally Band at Aquila's Nest Vineyards(2pm - 5pm) Newtown: Crash 21 at Perfusion Bar(8pm - 11pm) Old Greenwich: Mike and Chris at Bosco's Bar and Grill(9pm - 11:30pm) Redding: Caravan at Milestone(9pm - 11:30pm) Ridgefield: ACE & Friends in the Biergarten at Nod Hill Brewery, Ridgefield CT(5pm - 8pm) Stratford: DALE ALLEN + 41 NORTH at Blackbird's Nest(6pm) Stratford: Murray the wheel at Windmill Tavern(7pm) ⭐😂🎟️Stamford: Comedian Damon Wayans Jr at New York Comedy Club Stamford (5 SHOWS!)(7pm - 9:30pm) Stamford: Mugshot at Tiernan's Bar & Restaurant(9:30pm) Stamford: Outsyders LIVE at Third Place by Half Full Brewery(7pm - 10pm) ☀️🎶Westport: HOLLYWOOD NIGHTS – THE BOB SEGER EXPERIENCE at Levitt Pavilion(7pm) Westport: Hitch & the Giddyup at Walrus Alley(7:30pm - 10:30pm) Westport: Alter Ego at Black Duck Cafe(9pm) ☀️🎶Westport: Dan Tressler - Music on Church Lane(5:30pm –9pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(9am - 9:30pm) Woodbury: Little Lies: A Tribute to Fleetwood Mac LIVE at Woodbury Brewing Company(8:30pm - 11pm) Sunday, September 6, 2026 Bethel: SHE’S MY EX at Broken Symmetry Brew(12pm - 2pm) Bethel: Isabelle Rose at Notch8 Bar(5pm) Bethel: 3PM Dead Set with Nate and JD LIVE at Shakedown Street Eats(3pm) ☀️🎶Bridgeport: Luke Domozick at Twelvenote Brew Co.(2pm - 5pm) Bridgeport: The Bernadettes at Captain's Cove Seaport (Marina, Restaurant & Bar)(3pm - 7pm) ☀️🎶Bridgeport: Labor Day Family Picnic W/Six2Go - Sunday Night Music on the Dock at Port 5(3pm) Danbury: The Mad Hatters Swing Dance Party at Molly Darcy’s Irish Pub & Restaurant(6pm) Danbury: Danbury's Brazilian Festival(11am - 9pm) 🎪🛍️East Hampton: Haddam Neck Fair(7:30am -11pm) 🎪🛍️Goshen: Goshen Fair(8am - 9pm) ☀️🎶Milford: RumRunners - Walnut Beach Pavillion(4pm –7pm) New Milford: Third Annual Parrothead Party Celebrating Jimmy Buffett with JAMIE'S JUNK SHOW at Housatonic River Brewing(4pm - 7pm) ⭐🎟️Newtown: Fine Pastries and Wine Pairing at Aquila's Nest Vineyards(12pm) ⭐🎟️Newtown: Fleetwood Mac Tribute Show at Aquila's Nest Vineyards(6pm) ⭐🎶Newtown: Myron and the Jam Fam at Aquila's Nest Vineyards(2pm - 5pm) Newtown: Station Road at NewSylum Brewing Co.(2pm - 5pm) Norwalk: Emily Victoria at Washington Prime(12pm - 3pm) Norwalk: One Night Only at 314 Beer Garden(3pm -6pm) Norwalk: The James Barker Band | Wilson Conroy / Zach Ely at Bayley Beach(5:30pm - 8pm) Piermont, NY: Piano Brunch Sunday at OTTO'S(12pm - 3pm) Redding: Note to Self at Milestone(4pm) Ridgefield: Skylab at Nod Hill Brewery(3pm) Shelton: Sunday Jazz Series at The Gilded Whitlocks(2pm - 5pm) Shelton: What Up Funk at Spotted Horse Tavern(8pm) Stratford: Hatfield at Outriggers Restaurant(5pm - 8pm) Stratford: KATHY THOMPSON BAND at Blackbird's Nest(6pm) ⭐😂🎟️Stamford: Comedian Damon Wayans Jr at New York Comedy Club Stamford (5 SHOWS!)(4:30pm) Westport: Dave Savitsky Trio at Walrus Alley(12pm - 3pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(9am - 9:30pm) Monday, September 7, 2026 (Labor Day) ☀️🎶Bridgeport: Labor Day W/Ethyl Flying Soly - Sunday Night Music on the Dock at Port 5(2pm) Bridgeport: Eight to the Bar at Captain's Cove Seaport (Marina, Restaurant & Bar)(3:30pm - 7pm) 🎪🛍️East Hampton: Haddam Neck Fair(7:30pm - 5pm) 🎪🛍️Goshen: Goshen Fair(8am - 6pm) ⭐🎶Newtown: Mike Tedesco at Aquila's Nest Vineyards(2:30pm - 5:30pm) ☀️🎶Southport: Music Mondays at the Horseshoe Cafe, Southport(7pm) ⭐😂🎟️Stamford: Monday Night Mic at New York Comedy Club Stamford(7:30pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(9am - 7pm)
New Canaan, CT: Music lovers from across Fairfield County are invited to experience the inaugural New Canaan Music Festival on Saturday, September 19, 2026 , as the beautiful New Canaan Nature Center transforms into a full-day celebration of live music, community, and family entertainment. Presented by Michael-Louis Smith Music in partnership with the New Canaan Nature Center , the festival will showcase an impressive lineup of local and regional talent across two stages. Headlining the Main Stage is a special reunion performance by New York City's original rock band The Telephones , joined by Mind the Gap , Pretty Nasty , Take A Step Back , and THE DMR Big Band . The Festival Stage will feature performances from The Parkway Ramblers , Otis & The Hurricanes , Peter and His Band of Wolves , Mokra along with the family-friendly acoustic performance "Not For Kids Only," making this an event designed for music fans of all ages. Beyond the music, festivalgoers can enjoy food trucks, beverages, festival merchandise, local vendors, and activities for children while exploring the picturesque 40-acre New Canaan Nature Center , home to walking trails, ponds, gardens, a cattail marsh, and a scenic apple orchard. Gates open at 11:00 a.m. , with live music beginning at 12:00 noon and continuing until 10:00 p.m. The festival is rain or shine , and guests are encouraged to bring portable lawn chairs for comfortable seating throughout the day. Please note that overnight camping is not permitted. Whether you're discovering a new favorite band, enjoying the outdoors with family, or simply looking for one of Connecticut's newest music experiences, the First Annual New Canaan Music Festival promises a memorable day of live entertainment and community spirit. Event Details Date: Saturday, September 19, 2026 Location: New Canaan Nature Center, 144 Oenoke Ridge, New Canaan, CT Gates Open: 11:00 a.m. Music: Noon – 10:00 p.m. Rain or Shine Tickets and VIP Packages are available at: www.newcanaanmusicfestival.com
Brookfield, CT: A one-of-a-kind fall attraction is coming to Fairfield County as The Corn Maze at Twins BBQ Co. opens its third season on Saturday, September 5 , with this year’s five-acre maze dedicated to country music legend Dolly Parton . The special “Get Lost with Dolly” Corn Maze was planned well before Parton’s recent passing and was originally created to celebrate the beloved singer, songwriter, actress and philanthropist, along with the 31st anniversary of Dolly Parton’s Imagination Library . Now, the Brookfield attraction will also serve as a tribute to her extraordinary life and legacy. “We were going to honor her, and we’re now going to pay tribute to her,” Twins BBQ Co. co-owner Danielle Gallop told Hearst Connecticut Media. The Brookfield maze is part of a larger “Get Lost with Dolly” celebration taking place at 20 farms throughout the United States and Canada . The specially designed mazes were created by The MAiZE Inc. and are expected to welcome thousands of visitors throughout the fall season. Visitors to Twins BBQ Co. can expect much more than navigating their way through five acres of corn. Plans for the Dolly-themed experience include interactive trivia testing guests’ Dolly Parton knowledge, themed photo opportunities and additional activities celebrating her music, career and impact . Parton’s influence reaches far beyond country music. Known around the world for classics including “Jolene” and “I Will Always Love You,” she also built an enduring philanthropic legacy. Her Imagination Library has helped provide free books to children and encourage a lifelong love of reading. The Corn Maze at Twins BBQ Co . is scheduled to run from September 5 through November 7, 2026 , giving families and Dolly fans plenty of opportunities to experience this unique fall attraction right here in Brookfield. Whether you’re a lifelong Dolly Parton fan, looking for a fun fall outing or simply ready to see if you can find your way out, this year’s maze offers a memorable way to celebrate an American icon. 🌽 The Corn Maze at Twins BBQ Co. 📍 Brookfield, Connecticut 📅 September 5–November 7, 2026 🎟️ 2026 Theme: “Get Lost with Dolly” — A Tribute to Dolly Parton
Bridgeport, CT: GRAMMY-winning singer, songwriter, and guitar virtuoso Molly Tuttle is headed to The Klein Memorial Auditorium in Bridgeport on Sunday, September 6, 2026 at 7:30PM , bringing her distinctive blend of bluegrass, Americana, pop, and rock to Fairfield County. Recognized as one of the most dynamic artists in modern roots music, Tuttle has earned acclaim for both her extraordinary musicianship and her willingness to push beyond traditional genre boundaries. Her innovative guitar work, expressive songwriting, and powerful live performances have helped establish her as a groundbreaking voice in contemporary American music. In 2025, Tuttle released her fifth full-length album, So Long Little Miss Sunshine , one of her boldest and most personal projects to date. Recorded in Nashville with producer Mike Joyce , whose credits include Orville Peck, Miranda Lambert, and Lainey Wilson, the album explores themes of transformation, self-acceptance, and reinvention while expanding Tuttle's sound beyond her bluegrass roots. The album earned two GRAMMY® Award nominations , including Best Americana Album and Best Americana Performance for its lead single, “That’s Gonna Leave A Mark.” Tuttle's list of accomplishments continues to grow. She has received five GRAMMY nominations , including recognition in the Best New Artist category, and earned back-to-back GRAMMY wins for Best Bluegrass Album with her band Golden Highway . Crooked Tree took home the award in 2022, followed by City of Gold in 2023, making Tuttle the first artist in the category's history to win in consecutive years. She also made history as the first woman to receive the International Bluegrass Music Association's Guitar Player of the Year award and has earned multiple additional honors from the IBMA and Americana Music Awards. Now Fairfield County music fans will have the opportunity to experience Molly Tuttle live when she takes the stage at The Klein Memorial Auditorium in Bridgeport on September 6 . Mark your calendar and get ready for an evening with one of today's most celebrated and innovative roots musicians. Tickets are $56.50-$82.50.
Labor Day Weekend is here! 🇺🇸☀️ If you’re like me, you may be sticking around town instead of heading out for one last summer getaway. But that’s one of the great things about Fairfield County—you don’t have to travel far to make the weekend feel like a mini vacation! From traditional festivals and outdoor concerts to live music, comedy, wine and great food, there’s plenty happening throughout the area. While some are heading out of town, create your own daily getaway with our curated list of things to do in and around Fairfield County this Labor Day Weekend. Let’s start in Stamford , where one of our favorite comedy spots, New York Comedy Club Stamford , has an outstanding lineup. Thursday features TJ: The Alien Everywhere Tour , followed by Damon Wayans Jr. , taking over the club Friday, Saturday and Sunday. Check the NYCC Stamford calendar for available showtimes and tickets. Looking for live music instead? Jesse McCartney hits the stage at The Palace Theatre Stamford Friday night. And while you’re out and about in Stamford, don’t forget that Stamford Restaurant Week continues through September 7! It’s the perfect excuse to try a restaurant you’ve been meaning to visit or make reservations at one of your longtime local favorites. The options are yours! 🍽️ On Saturday night, head to Edmond Town Hall for The Insiders: A Tribute to Tom Petty . At one of our favorite vineyards, Aquila’s Nest Vineyards , the weekend kicks into high gear Saturday with Dueling Pianos featuring The Flying Ivories . Then on Sunday at 6 PM, Little Lies – A Fleetwood Mac Tribute returns to the vineyard. Over in Ridgefield , head to Odeen’s Friday evening for Music on the Porch with Phil & Isabelle from 5:30–8:30 PM. Or get an early start on the weekend Thursday with Trivia Night at Odeen’s at Oak Hills —make your reservations and put your trivia skills to the test! And if you’re in a foodie mood, come hungry! 🍽️🌎 ConnectFairfield presents the 2nd Annual Fairfield International Food Festival on Saturday from 4–8 PM. Explore international flavors, enjoy the festivities and grab your tickets in advance. And this is only the beginning! Check out Fairfield After Dark’s complete Labor Day Weekend Happenings and start planning your own local getaway. Wednesday, September 2, 2026 Danbury: Wed Open Mic at Sugar Hollow Taproom(7pm) Fairfield: Music with The Lamb Jam at The Seagrape Fairfield(8:30pm) ☀️🎶New Canaan: The Short Bus Band – 70’s to Today’s Hits at Waveny Park(7:30 – 9:30pm) ⭐🎟️Newtown: Fairfield Alumni Happy Hour at Aquila's Nest Vineyards(5:30pm) ⭐🎟️Newtown: Pilates + Pour with Mia at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Reiki & Rosé at Aquila's Nest Vineyards(6pm) Norwalk: Detroy Langer & Riccio Organ Trio at Greer Southern Table(6pm - 9pm) ☀️🎶Norwalk: Funk Salsa Urban at Calf Pasture Beach(7pm) Shelton: Benny at Spotted Horse Tavern(8pm) Thursday, September 3, 2026 Bethel: FIDDLERS'S BRAWL at Whitlock’s Restaurant(6pm - 9pm) Danbury: Thursday Open Jam with Fuzz on It LIVE at Sugar Hollow Taproom(8pm) Fairfield: ETA Music at The Sinclair(8:30pm) Milford: Greg McCarthy at Cafe Atlantique(5pm) ⭐🎟️Newtown: Wine, Words & Wisdom Book Club Series at Aquila's Nest Vineyards(6:30pm) ⭐🎶Newtown: Joan Wallace at Aquila's Nest Vineyards(5:30pm) 🍔🍺🧠Norwalk: Trivia Night at ODEEN'S(7pm - 9pm) Old Greenwich: Mojo at Bosco's Bar and Grill(8:30pm) Shelton: Jack + Allie at The Gilded Whitlocks(6pm) Stratford: PAT MATTO at Blackbird's Nest(5pm) ⭐😂🎟️Stamford: Comedian TJ: The Alien Everywhere Tour at New York Comedy Club Stamford(7pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(4pm - 9:30pm) Friday, September 4, 2026 Bethel: Note To Self at Shakedown Street Eats(6:30pm) Bethel: Mystery Train at Notch8 Bar(8pm) Bethel: BRENNAN MUSIC at Whitlock’s Restaurant(6pm - 9pm) ☀️🎶Bethlehem: Hype at March Farms Hilltop (6-8pm) ☀️🎶Brookfield: DAN'S GARAGE at the Summer Concerts in the Park - Brookfield (6:30pm) ☀️🎶Bridgeport: Josh A - Friday Night Music on the Dock at Port 5(5pm –8:30pm) ☀️🎶Bridgeport: Cat Lines at Twelvenote Brew Co.(7pm - 10pm) Danbury: Roll n Roll Collective LIVE at Sugar Hollow Taproom(8:30pm) 🎪🛍️East Hampton: Haddam Neck Fair(3pm - 11pm) Milford: Tim Payson at Cafe Atlantique(6:30pm) New Milford: Lost Rebel at Housatonic River Brewing(7pm - 10pm) ⭐🎟️Newtown: Llamas and Llibations at Aquila's Nest Vineyards(5:30pm) ⭐🎟️Newtown: Baked Brie & Vino Night at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Speed Dating Ages 60+ at Aquila's Nest Vineyards(7pm) ⭐🎶Newtown: Glenn Roth at Aquila's Nest Vineyards(5:30pm - 8:30pm) Newtown: Willy Portera Trio at NewSylum Brewing Co.(6pm - 9pm) Norwalk: Pimpinella at 314 Beer Garden(7:30pm - 11pm) Norwalk: Billy G & Friends at Sails American Grill(9pm - 12am) Ridgefield: Tom Petty Night at Nod Hill Brewery(6:30pm) ⭐🍽️ 🎶Ridgefield: Isabelle & Phil on the Porch at Odeen's Ridgefield(5:30pm - 8:30pm) Sherman: Dinner & Music with Bernie Kaplan: "Yesterday and Tomorrow, Today" at JCC in Sherman(7pm - 9pm) Stratford: Brandon Mullis solo at Windmill Tavern(5pm) Stratford: TIN SANDWICH at Blackbird's Nest(6pm) Stratford: Bad Mannerz at Windmill Tavern(8pm) Stamford: Plastercade at Tiernan's Bar & Restaurant(1pm - 2pm) Stamford: Bad Saints LIVE at Third Place by Half Full Brewery(8pm - 10pm) ⭐😂🎟️Stamford: Comedian Damon Wayans Jr at New York Comedy Club Stamford (5 SHOWS!)(7pm - 9:30pm) ⭐🎟️Stamford: Jesse McCartney The Weightless Tour at The Palace Theatre Stamford(8pm) ☀️🎶Westport: Steve Ferentzy - Music on Church Lane(5:30pm –9pm) Westport: MIHALI * Full Band Show * w/ Mr Mota at Levitt Pavilion(4:30pm) Westport: Jonathan Niles Chapman at Walrus Alley(7:30pm - 10:30pm) Westport: Herman and Co. at Black Duck Cafe(9pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(12pm - 9:30pm) Saturday, September 5, 2026 Bethel: Iris Lies at Notch8 Bar(8pm) Bethel: Seth Adam LIVE at Shakedown Street Eats(6:30pm - 9:30pm) Bethel: Sound Dog LIVE at DragonFly(6pm - 9pm) Bethel: MORRIGAN’S CROSSING LIVE at Whitlock’s Restaurant(6pm - 9pm) Bridgeport: Midnight Cardinal at Captain's Cove Seaport (Marina, Restaurant & Bar)(4pm - 8pm) ☀️🎶Bridgeport: The Brother Cool Duo at Twelvenote Brew Co.(7pm - 10pm) Brookfield: Rio Sorrentino at Pulcinella(7pm - 10pm) Danbury: Danbury's Brazilian Festival(11am - 10pm) Danbury: Core. 90s and 2000s Alternative Rock LIVE at Sugar Hollow Taproom(8:30pm) 🎪🛍️East Hampton: Haddam Neck Fair(7:30pm - 11pm) 🌍🍽️ Fairfield: Fairfield International Food Festival at FTC(4pm - 8pm) 🎪🛍️Goshen: Goshen Fair(8am - 9pm) Milford: Shannon McMahon at Cafe Atlantique(6:30pm) New Milford: Street Survivors - Tribute to Lynyrd Skynyrd at Housatonic River Brewing(7pm - 10pm) ⭐🎟️Newtown: Cheesecakes & Wine Pairing at Aquila's Nest Vineyards(12pm) ⭐🎟️Newtown: Whiskers & Wine Kitten Adoption Event at Aquila's Nest Vineyards(12pm) ⭐🎟️Newtown: Dueling Pianos with the Flying Ivories at Aquila's Nest Vineyards(6pm) ⭐🎶Newtown: Red Planet(Dead/Garcia Tribute) at NewSylum Brewing Co.(3pm - 6pm) ⭐🎟️Newtown: The Insiders: Tribute to Tom Petty coming to Edmond Town Hall(8pm - 10pm) Newtown: Teacup Sally Band at Aquila's Nest Vineyards(2pm - 5pm) Newtown: Crash 21 at Perfusion Bar(8pm - 11pm) Old Greenwich: Mike and Chris at Bosco's Bar and Grill(9pm - 11:30pm) Redding: Caravan at Milestone(9pm - 11:30pm) Ridgefield: ACE & Friends in the Biergarten at Nod Hill Brewery, Ridgefield CT(5pm - 8pm) Stratford: DALE ALLEN + 41 NORTH at Blackbird's Nest(6pm) Stratford: Murray the wheel at Windmill Tavern(7pm) ⭐😂🎟️Stamford: Comedian Damon Wayans Jr at New York Comedy Club Stamford (5 SHOWS!)(7pm - 9:30pm) Stamford: Mugshot at Tiernan's Bar & Restaurant(9:30pm) Stamford: Outsyders LIVE at Third Place by Half Full Brewery(7pm - 10pm) ☀️🎶Westport: HOLLYWOOD NIGHTS – THE BOB SEGER EXPERIENCE at Levitt Pavilion(7pm) Westport: Hitch & the Giddyup at Walrus Alley(7:30pm - 10:30pm) Westport: Alter Ego at Black Duck Cafe(9pm) ☀️🎶Westport: Dan Tressler - Music on Church Lane(5:30pm –9pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(9am - 9:30pm) Woodbury: Little Lies: A Tribute to Fleetwood Mac LIVE at Woodbury Brewing Company(8:30pm - 11pm) Sunday, September 6, 2026 Bethel: SHE’S MY EX at Broken Symmetry Brew(12pm - 2pm) Bethel: Isabelle Rose at Notch8 Bar(5pm) Bethel: 3PM Dead Set with Nate and JD LIVE at Shakedown Street Eats(3pm) ☀️🎶Bridgeport: Luke Domozick at Twelvenote Brew Co.(2pm - 5pm) Bridgeport: The Bernadettes at Captain's Cove Seaport (Marina, Restaurant & Bar)(3pm - 7pm) ☀️🎶Bridgeport: Labor Day Family Picnic W/Six2Go - Sunday Night Music on the Dock at Port 5(3pm) Danbury: The Mad Hatters Swing Dance Party at Molly Darcy’s Irish Pub & Restaurant(6pm) Danbury: Danbury's Brazilian Festival(11am - 9pm) 🎪🛍️East Hampton: Haddam Neck Fair(7:30am -11pm) 🎪🛍️Goshen: Goshen Fair(8am - 9pm) ☀️🎶Milford: RumRunners - Walnut Beach Pavillion(4pm –7pm) New Milford: Third Annual Parrothead Party Celebrating Jimmy Buffett with JAMIE'S JUNK SHOW at Housatonic River Brewing(4pm - 7pm) ⭐🎟️Newtown: Fine Pastries and Wine Pairing at Aquila's Nest Vineyards(12pm) ⭐🎟️Newtown: Fleetwood Mac Tribute Show at Aquila's Nest Vineyards(6pm) ⭐🎶Newtown: Myron and the Jam Fam at Aquila's Nest Vineyards(2pm - 5pm) Newtown: Station Road at NewSylum Brewing Co.(2pm - 5pm) Norwalk: Emily Victoria at Washington Prime(12pm - 3pm) Norwalk: One Night Only at 314 Beer Garden(3pm -6pm) Norwalk: The James Barker Band | Wilson Conroy / Zach Ely at Bayley Beach(5:30pm - 8pm) Piermont, NY: Piano Brunch Sunday at OTTO'S(12pm - 3pm) Redding: Note to Self at Milestone(4pm) Ridgefield: Skylab at Nod Hill Brewery(3pm) Shelton: Sunday Jazz Series at The Gilded Whitlocks(2pm - 5pm) Shelton: What Up Funk at Spotted Horse Tavern(8pm) Stratford: Hatfield at Outriggers Restaurant(5pm - 8pm) Stratford: KATHY THOMPSON BAND at Blackbird's Nest(6pm) ⭐😂🎟️Stamford: Comedian Damon Wayans Jr at New York Comedy Club Stamford (5 SHOWS!)(4:30pm) Westport: Dave Savitsky Trio at Walrus Alley(12pm - 3pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(9am - 9:30pm) Monday, September 7, 2026 (Labor Day) ☀️🎶Bridgeport: Labor Day W/Ethyl Flying Soly - Sunday Night Music on the Dock at Port 5(2pm) Bridgeport: Eight to the Bar at Captain's Cove Seaport (Marina, Restaurant & Bar)(3:30pm - 7pm) 🎪🛍️East Hampton: Haddam Neck Fair(7:30pm - 5pm) 🎪🛍️Goshen: Goshen Fair(8am - 6pm) ⭐🎶Newtown: Mike Tedesco at Aquila's Nest Vineyards(2:30pm - 5:30pm) ☀️🎶Southport: Music Mondays at the Horseshoe Cafe, Southport(7pm) ⭐😂🎟️Stamford: Monday Night Mic at New York Comedy Club Stamford(7:30pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(9am - 7pm)
New Canaan, CT: Music lovers from across Fairfield County are invited to experience the inaugural New Canaan Music Festival on Saturday, September 19, 2026 , as the beautiful New Canaan Nature Center transforms into a full-day celebration of live music, community, and family entertainment. Presented by Michael-Louis Smith Music in partnership with the New Canaan Nature Center , the festival will showcase an impressive lineup of local and regional talent across two stages. Headlining the Main Stage is a special reunion performance by New York City's original rock band The Telephones , joined by Mind the Gap , Pretty Nasty , Take A Step Back , and THE DMR Big Band . The Festival Stage will feature performances from The Parkway Ramblers , Otis & The Hurricanes , Peter and His Band of Wolves , Mokra along with the family-friendly acoustic performance "Not For Kids Only," making this an event designed for music fans of all ages. Beyond the music, festivalgoers can enjoy food trucks, beverages, festival merchandise, local vendors, and activities for children while exploring the picturesque 40-acre New Canaan Nature Center , home to walking trails, ponds, gardens, a cattail marsh, and a scenic apple orchard. Gates open at 11:00 a.m. , with live music beginning at 12:00 noon and continuing until 10:00 p.m. The festival is rain or shine , and guests are encouraged to bring portable lawn chairs for comfortable seating throughout the day. Please note that overnight camping is not permitted. Whether you're discovering a new favorite band, enjoying the outdoors with family, or simply looking for one of Connecticut's newest music experiences, the First Annual New Canaan Music Festival promises a memorable day of live entertainment and community spirit. Event Details Date: Saturday, September 19, 2026 Location: New Canaan Nature Center, 144 Oenoke Ridge, New Canaan, CT Gates Open: 11:00 a.m. Music: Noon – 10:00 p.m. Rain or Shine Tickets and VIP Packages are available at: www.newcanaanmusicfestival.com
Brookfield, CT: A one-of-a-kind fall attraction is coming to Fairfield County as The Corn Maze at Twins BBQ Co. opens its third season on Saturday, September 5 , with this year’s five-acre maze dedicated to country music legend Dolly Parton . The special “Get Lost with Dolly” Corn Maze was planned well before Parton’s recent passing and was originally created to celebrate the beloved singer, songwriter, actress and philanthropist, along with the 31st anniversary of Dolly Parton’s Imagination Library . Now, the Brookfield attraction will also serve as a tribute to her extraordinary life and legacy. “We were going to honor her, and we’re now going to pay tribute to her,” Twins BBQ Co. co-owner Danielle Gallop told Hearst Connecticut Media. The Brookfield maze is part of a larger “Get Lost with Dolly” celebration taking place at 20 farms throughout the United States and Canada . The specially designed mazes were created by The MAiZE Inc. and are expected to welcome thousands of visitors throughout the fall season. Visitors to Twins BBQ Co. can expect much more than navigating their way through five acres of corn. Plans for the Dolly-themed experience include interactive trivia testing guests’ Dolly Parton knowledge, themed photo opportunities and additional activities celebrating her music, career and impact . Parton’s influence reaches far beyond country music. Known around the world for classics including “Jolene” and “I Will Always Love You,” she also built an enduring philanthropic legacy. Her Imagination Library has helped provide free books to children and encourage a lifelong love of reading. The Corn Maze at Twins BBQ Co . is scheduled to run from September 5 through November 7, 2026 , giving families and Dolly fans plenty of opportunities to experience this unique fall attraction right here in Brookfield. Whether you’re a lifelong Dolly Parton fan, looking for a fun fall outing or simply ready to see if you can find your way out, this year’s maze offers a memorable way to celebrate an American icon. 🌽 The Corn Maze at Twins BBQ Co. 📍 Brookfield, Connecticut 📅 September 5–November 7, 2026 🎟️ 2026 Theme: “Get Lost with Dolly” — A Tribute to Dolly Parton
Bridgeport, CT: GRAMMY-winning singer, songwriter, and guitar virtuoso Molly Tuttle is headed to The Klein Memorial Auditorium in Bridgeport on Sunday, September 6, 2026 at 7:30PM , bringing her distinctive blend of bluegrass, Americana, pop, and rock to Fairfield County. Recognized as one of the most dynamic artists in modern roots music, Tuttle has earned acclaim for both her extraordinary musicianship and her willingness to push beyond traditional genre boundaries. Her innovative guitar work, expressive songwriting, and powerful live performances have helped establish her as a groundbreaking voice in contemporary American music. In 2025, Tuttle released her fifth full-length album, So Long Little Miss Sunshine , one of her boldest and most personal projects to date. Recorded in Nashville with producer Mike Joyce , whose credits include Orville Peck, Miranda Lambert, and Lainey Wilson, the album explores themes of transformation, self-acceptance, and reinvention while expanding Tuttle's sound beyond her bluegrass roots. The album earned two GRAMMY® Award nominations , including Best Americana Album and Best Americana Performance for its lead single, “That’s Gonna Leave A Mark.” Tuttle's list of accomplishments continues to grow. She has received five GRAMMY nominations , including recognition in the Best New Artist category, and earned back-to-back GRAMMY wins for Best Bluegrass Album with her band Golden Highway . Crooked Tree took home the award in 2022, followed by City of Gold in 2023, making Tuttle the first artist in the category's history to win in consecutive years. She also made history as the first woman to receive the International Bluegrass Music Association's Guitar Player of the Year award and has earned multiple additional honors from the IBMA and Americana Music Awards. Now Fairfield County music fans will have the opportunity to experience Molly Tuttle live when she takes the stage at The Klein Memorial Auditorium in Bridgeport on September 6 . Mark your calendar and get ready for an evening with one of today's most celebrated and innovative roots musicians. Tickets are $56.50-$82.50.
Labor Day Weekend is here! 🇺🇸☀️ If you’re like me, you may be sticking around town instead of heading out for one last summer getaway. But that’s one of the great things about Fairfield County—you don’t have to travel far to make the weekend feel like a mini vacation! From traditional festivals and outdoor concerts to live music, comedy, wine and great food, there’s plenty happening throughout the area. While some are heading out of town, create your own daily getaway with our curated list of things to do in and around Fairfield County this Labor Day Weekend. Let’s start in Stamford , where one of our favorite comedy spots, New York Comedy Club Stamford , has an outstanding lineup. Thursday features TJ: The Alien Everywhere Tour , followed by Damon Wayans Jr. , taking over the club Friday, Saturday and Sunday. Check the NYCC Stamford calendar for available showtimes and tickets. Looking for live music instead? Jesse McCartney hits the stage at The Palace Theatre Stamford Friday night. And while you’re out and about in Stamford, don’t forget that Stamford Restaurant Week continues through September 7! It’s the perfect excuse to try a restaurant you’ve been meaning to visit or make reservations at one of your longtime local favorites. The options are yours! 🍽️ On Saturday night, head to Edmond Town Hall for The Insiders: A Tribute to Tom Petty . At one of our favorite vineyards, Aquila’s Nest Vineyards , the weekend kicks into high gear Saturday with Dueling Pianos featuring The Flying Ivories . Then on Sunday at 6 PM, Little Lies – A Fleetwood Mac Tribute returns to the vineyard. Over in Ridgefield , head to Odeen’s Friday evening for Music on the Porch with Phil & Isabelle from 5:30–8:30 PM. Or get an early start on the weekend Thursday with Trivia Night at Odeen’s at Oak Hills —make your reservations and put your trivia skills to the test! And if you’re in a foodie mood, come hungry! 🍽️🌎 ConnectFairfield presents the 2nd Annual Fairfield International Food Festival on Saturday from 4–8 PM. Explore international flavors, enjoy the festivities and grab your tickets in advance. And this is only the beginning! Check out Fairfield After Dark’s complete Labor Day Weekend Happenings and start planning your own local getaway. Wednesday, September 2, 2026 Danbury: Wed Open Mic at Sugar Hollow Taproom(7pm) Fairfield: Music with The Lamb Jam at The Seagrape Fairfield(8:30pm) ☀️🎶New Canaan: The Short Bus Band – 70’s to Today’s Hits at Waveny Park(7:30 – 9:30pm) ⭐🎟️Newtown: Fairfield Alumni Happy Hour at Aquila's Nest Vineyards(5:30pm) ⭐🎟️Newtown: Pilates + Pour with Mia at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Reiki & Rosé at Aquila's Nest Vineyards(6pm) Norwalk: Detroy Langer & Riccio Organ Trio at Greer Southern Table(6pm - 9pm) ☀️🎶Norwalk: Funk Salsa Urban at Calf Pasture Beach(7pm) Shelton: Benny at Spotted Horse Tavern(8pm) Thursday, September 3, 2026 Bethel: FIDDLERS'S BRAWL at Whitlock’s Restaurant(6pm - 9pm) Danbury: Thursday Open Jam with Fuzz on It LIVE at Sugar Hollow Taproom(8pm) Fairfield: ETA Music at The Sinclair(8:30pm) Milford: Greg McCarthy at Cafe Atlantique(5pm) ⭐🎟️Newtown: Wine, Words & Wisdom Book Club Series at Aquila's Nest Vineyards(6:30pm) ⭐🎶Newtown: Joan Wallace at Aquila's Nest Vineyards(5:30pm) 🍔🍺🧠Norwalk: Trivia Night at ODEEN'S(7pm - 9pm) Old Greenwich: Mojo at Bosco's Bar and Grill(8:30pm) Shelton: Jack + Allie at The Gilded Whitlocks(6pm) Stratford: PAT MATTO at Blackbird's Nest(5pm) ⭐😂🎟️Stamford: Comedian TJ: The Alien Everywhere Tour at New York Comedy Club Stamford(7pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(4pm - 9:30pm) Friday, September 4, 2026 Bethel: Note To Self at Shakedown Street Eats(6:30pm) Bethel: Mystery Train at Notch8 Bar(8pm) Bethel: BRENNAN MUSIC at Whitlock’s Restaurant(6pm - 9pm) ☀️🎶Bethlehem: Hype at March Farms Hilltop (6-8pm) ☀️🎶Brookfield: DAN'S GARAGE at the Summer Concerts in the Park - Brookfield (6:30pm) ☀️🎶Bridgeport: Josh A - Friday Night Music on the Dock at Port 5(5pm –8:30pm) ☀️🎶Bridgeport: Cat Lines at Twelvenote Brew Co.(7pm - 10pm) Danbury: Roll n Roll Collective LIVE at Sugar Hollow Taproom(8:30pm) 🎪🛍️East Hampton: Haddam Neck Fair(3pm - 11pm) Milford: Tim Payson at Cafe Atlantique(6:30pm) New Milford: Lost Rebel at Housatonic River Brewing(7pm - 10pm) ⭐🎟️Newtown: Llamas and Llibations at Aquila's Nest Vineyards(5:30pm) ⭐🎟️Newtown: Baked Brie & Vino Night at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Speed Dating Ages 60+ at Aquila's Nest Vineyards(7pm) ⭐🎶Newtown: Glenn Roth at Aquila's Nest Vineyards(5:30pm - 8:30pm) Newtown: Willy Portera Trio at NewSylum Brewing Co.(6pm - 9pm) Norwalk: Pimpinella at 314 Beer Garden(7:30pm - 11pm) Norwalk: Billy G & Friends at Sails American Grill(9pm - 12am) Ridgefield: Tom Petty Night at Nod Hill Brewery(6:30pm) ⭐🍽️ 🎶Ridgefield: Isabelle & Phil on the Porch at Odeen's Ridgefield(5:30pm - 8:30pm) Sherman: Dinner & Music with Bernie Kaplan: "Yesterday and Tomorrow, Today" at JCC in Sherman(7pm - 9pm) Stratford: Brandon Mullis solo at Windmill Tavern(5pm) Stratford: TIN SANDWICH at Blackbird's Nest(6pm) Stratford: Bad Mannerz at Windmill Tavern(8pm) Stamford: Plastercade at Tiernan's Bar & Restaurant(1pm - 2pm) Stamford: Bad Saints LIVE at Third Place by Half Full Brewery(8pm - 10pm) ⭐😂🎟️Stamford: Comedian Damon Wayans Jr at New York Comedy Club Stamford (5 SHOWS!)(7pm - 9:30pm) ⭐🎟️Stamford: Jesse McCartney The Weightless Tour at The Palace Theatre Stamford(8pm) ☀️🎶Westport: Steve Ferentzy - Music on Church Lane(5:30pm –9pm) Westport: MIHALI * Full Band Show * w/ Mr Mota at Levitt Pavilion(4:30pm) Westport: Jonathan Niles Chapman at Walrus Alley(7:30pm - 10:30pm) Westport: Herman and Co. at Black Duck Cafe(9pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(12pm - 9:30pm) Saturday, September 5, 2026 Bethel: Iris Lies at Notch8 Bar(8pm) Bethel: Seth Adam LIVE at Shakedown Street Eats(6:30pm - 9:30pm) Bethel: Sound Dog LIVE at DragonFly(6pm - 9pm) Bethel: MORRIGAN’S CROSSING LIVE at Whitlock’s Restaurant(6pm - 9pm) Bridgeport: Midnight Cardinal at Captain's Cove Seaport (Marina, Restaurant & Bar)(4pm - 8pm) ☀️🎶Bridgeport: The Brother Cool Duo at Twelvenote Brew Co.(7pm - 10pm) Brookfield: Rio Sorrentino at Pulcinella(7pm - 10pm) Danbury: Danbury's Brazilian Festival(11am - 10pm) Danbury: Core. 90s and 2000s Alternative Rock LIVE at Sugar Hollow Taproom(8:30pm) 🎪🛍️East Hampton: Haddam Neck Fair(7:30pm - 11pm) 🌍🍽️ Fairfield: Fairfield International Food Festival at FTC(4pm - 8pm) 🎪🛍️Goshen: Goshen Fair(8am - 9pm) Milford: Shannon McMahon at Cafe Atlantique(6:30pm) New Milford: Street Survivors - Tribute to Lynyrd Skynyrd at Housatonic River Brewing(7pm - 10pm) ⭐🎟️Newtown: Cheesecakes & Wine Pairing at Aquila's Nest Vineyards(12pm) ⭐🎟️Newtown: Whiskers & Wine Kitten Adoption Event at Aquila's Nest Vineyards(12pm) ⭐🎟️Newtown: Dueling Pianos with the Flying Ivories at Aquila's Nest Vineyards(6pm) ⭐🎶Newtown: Red Planet(Dead/Garcia Tribute) at NewSylum Brewing Co.(3pm - 6pm) ⭐🎟️Newtown: The Insiders: Tribute to Tom Petty coming to Edmond Town Hall(8pm - 10pm) Newtown: Teacup Sally Band at Aquila's Nest Vineyards(2pm - 5pm) Newtown: Crash 21 at Perfusion Bar(8pm - 11pm) Old Greenwich: Mike and Chris at Bosco's Bar and Grill(9pm - 11:30pm) Redding: Caravan at Milestone(9pm - 11:30pm) Ridgefield: ACE & Friends in the Biergarten at Nod Hill Brewery, Ridgefield CT(5pm - 8pm) Stratford: DALE ALLEN + 41 NORTH at Blackbird's Nest(6pm) Stratford: Murray the wheel at Windmill Tavern(7pm) ⭐😂🎟️Stamford: Comedian Damon Wayans Jr at New York Comedy Club Stamford (5 SHOWS!)(7pm - 9:30pm) Stamford: Mugshot at Tiernan's Bar & Restaurant(9:30pm) Stamford: Outsyders LIVE at Third Place by Half Full Brewery(7pm - 10pm) ☀️🎶Westport: HOLLYWOOD NIGHTS – THE BOB SEGER EXPERIENCE at Levitt Pavilion(7pm) Westport: Hitch & the Giddyup at Walrus Alley(7:30pm - 10:30pm) Westport: Alter Ego at Black Duck Cafe(9pm) ☀️🎶Westport: Dan Tressler - Music on Church Lane(5:30pm –9pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(9am - 9:30pm) Woodbury: Little Lies: A Tribute to Fleetwood Mac LIVE at Woodbury Brewing Company(8:30pm - 11pm) Sunday, September 6, 2026 Bethel: SHE’S MY EX at Broken Symmetry Brew(12pm - 2pm) Bethel: Isabelle Rose at Notch8 Bar(5pm) Bethel: 3PM Dead Set with Nate and JD LIVE at Shakedown Street Eats(3pm) ☀️🎶Bridgeport: Luke Domozick at Twelvenote Brew Co.(2pm - 5pm) Bridgeport: The Bernadettes at Captain's Cove Seaport (Marina, Restaurant & Bar)(3pm - 7pm) ☀️🎶Bridgeport: Labor Day Family Picnic W/Six2Go - Sunday Night Music on the Dock at Port 5(3pm) Danbury: The Mad Hatters Swing Dance Party at Molly Darcy’s Irish Pub & Restaurant(6pm) Danbury: Danbury's Brazilian Festival(11am - 9pm) 🎪🛍️East Hampton: Haddam Neck Fair(7:30am -11pm) 🎪🛍️Goshen: Goshen Fair(8am - 9pm) ☀️🎶Milford: RumRunners - Walnut Beach Pavillion(4pm –7pm) New Milford: Third Annual Parrothead Party Celebrating Jimmy Buffett with JAMIE'S JUNK SHOW at Housatonic River Brewing(4pm - 7pm) ⭐🎟️Newtown: Fine Pastries and Wine Pairing at Aquila's Nest Vineyards(12pm) ⭐🎟️Newtown: Fleetwood Mac Tribute Show at Aquila's Nest Vineyards(6pm) ⭐🎶Newtown: Myron and the Jam Fam at Aquila's Nest Vineyards(2pm - 5pm) Newtown: Station Road at NewSylum Brewing Co.(2pm - 5pm) Norwalk: Emily Victoria at Washington Prime(12pm - 3pm) Norwalk: One Night Only at 314 Beer Garden(3pm -6pm) Norwalk: The James Barker Band | Wilson Conroy / Zach Ely at Bayley Beach(5:30pm - 8pm) Piermont, NY: Piano Brunch Sunday at OTTO'S(12pm - 3pm) Redding: Note to Self at Milestone(4pm) Ridgefield: Skylab at Nod Hill Brewery(3pm) Shelton: Sunday Jazz Series at The Gilded Whitlocks(2pm - 5pm) Shelton: What Up Funk at Spotted Horse Tavern(8pm) Stratford: Hatfield at Outriggers Restaurant(5pm - 8pm) Stratford: KATHY THOMPSON BAND at Blackbird's Nest(6pm) ⭐😂🎟️Stamford: Comedian Damon Wayans Jr at New York Comedy Club Stamford (5 SHOWS!)(4:30pm) Westport: Dave Savitsky Trio at Walrus Alley(12pm - 3pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(9am - 9:30pm) Monday, September 7, 2026 (Labor Day) ☀️🎶Bridgeport: Labor Day W/Ethyl Flying Soly - Sunday Night Music on the Dock at Port 5(2pm) Bridgeport: Eight to the Bar at Captain's Cove Seaport (Marina, Restaurant & Bar)(3:30pm - 7pm) 🎪🛍️East Hampton: Haddam Neck Fair(7:30pm - 5pm) 🎪🛍️Goshen: Goshen Fair(8am - 6pm) ⭐🎶Newtown: Mike Tedesco at Aquila's Nest Vineyards(2:30pm - 5:30pm) ☀️🎶Southport: Music Mondays at the Horseshoe Cafe, Southport(7pm) ⭐😂🎟️Stamford: Monday Night Mic at New York Comedy Club Stamford(7:30pm) 🎪🎆🎠Woodstock: The 165th Woodstock Fair(9am - 7pm)
New Canaan, CT: Music lovers from across Fairfield County are invited to experience the inaugural New Canaan Music Festival on Saturday, September 19, 2026 , as the beautiful New Canaan Nature Center transforms into a full-day celebration of live music, community, and family entertainment. Presented by Michael-Louis Smith Music in partnership with the New Canaan Nature Center , the festival will showcase an impressive lineup of local and regional talent across two stages. Headlining the Main Stage is a special reunion performance by New York City's original rock band The Telephones , joined by Mind the Gap , Pretty Nasty , Take A Step Back , and THE DMR Big Band . The Festival Stage will feature performances from The Parkway Ramblers , Otis & The Hurricanes , Peter and His Band of Wolves , Mokra along with the family-friendly acoustic performance "Not For Kids Only," making this an event designed for music fans of all ages. Beyond the music, festivalgoers can enjoy food trucks, beverages, festival merchandise, local vendors, and activities for children while exploring the picturesque 40-acre New Canaan Nature Center , home to walking trails, ponds, gardens, a cattail marsh, and a scenic apple orchard. Gates open at 11:00 a.m. , with live music beginning at 12:00 noon and continuing until 10:00 p.m. The festival is rain or shine , and guests are encouraged to bring portable lawn chairs for comfortable seating throughout the day. Please note that overnight camping is not permitted. Whether you're discovering a new favorite band, enjoying the outdoors with family, or simply looking for one of Connecticut's newest music experiences, the First Annual New Canaan Music Festival promises a memorable day of live entertainment and community spirit. Event Details Date: Saturday, September 19, 2026 Location: New Canaan Nature Center, 144 Oenoke Ridge, New Canaan, CT Gates Open: 11:00 a.m. Music: Noon – 10:00 p.m. Rain or Shine Tickets and VIP Packages are available at: www.newcanaanmusicfestival.com
Brookfield, CT: A one-of-a-kind fall attraction is coming to Fairfield County as The Corn Maze at Twins BBQ Co. opens its third season on Saturday, September 5 , with this year’s five-acre maze dedicated to country music legend Dolly Parton . The special “Get Lost with Dolly” Corn Maze was planned well before Parton’s recent passing and was originally created to celebrate the beloved singer, songwriter, actress and philanthropist, along with the 31st anniversary of Dolly Parton’s Imagination Library . Now, the Brookfield attraction will also serve as a tribute to her extraordinary life and legacy. “We were going to honor her, and we’re now going to pay tribute to her,” Twins BBQ Co. co-owner Danielle Gallop told Hearst Connecticut Media. The Brookfield maze is part of a larger “Get Lost with Dolly” celebration taking place at 20 farms throughout the United States and Canada . The specially designed mazes were created by The MAiZE Inc. and are expected to welcome thousands of visitors throughout the fall season. Visitors to Twins BBQ Co. can expect much more than navigating their way through five acres of corn. Plans for the Dolly-themed experience include interactive trivia testing guests’ Dolly Parton knowledge, themed photo opportunities and additional activities celebrating her music, career and impact . Parton’s influence reaches far beyond country music. Known around the world for classics including “Jolene” and “I Will Always Love You,” she also built an enduring philanthropic legacy. Her Imagination Library has helped provide free books to children and encourage a lifelong love of reading. The Corn Maze at Twins BBQ Co . is scheduled to run from September 5 through November 7, 2026 , giving families and Dolly fans plenty of opportunities to experience this unique fall attraction right here in Brookfield. Whether you’re a lifelong Dolly Parton fan, looking for a fun fall outing or simply ready to see if you can find your way out, this year’s maze offers a memorable way to celebrate an American icon. 🌽 The Corn Maze at Twins BBQ Co. 📍 Brookfield, Connecticut 📅 September 5–November 7, 2026 🎟️ 2026 Theme: “Get Lost with Dolly” — A Tribute to Dolly Parton
