Explore Fairfield County’s Best Events This Week!

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) ⭐😂🎟️Stamford: HEAVVY HITTERS ft. Heavvy and Friends at New York Comedy Club Stamford(7pm) 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.

As summer begins to wind down, there’s still plenty happening in and around Fairfield County! Free town-sponsored outdoor concerts continue throughout the area, while annual favorite Festivals & Fairs including the Dutchess County Fair, Brooklyn Fair , Terryville Lions Country Fair and more return this week. Be sure to check out FAD’s Summer Event Calendar for the full lineup. Looking for live entertainment? Charles Esten takes the stage at Edmond Town Hall on Friday, August 28 . New York Comedy Club Stamford has a packed weekend with Emil Wakim on Thursday, Rachel Feinstein Friday and Saturday , and Juston McKinney on Sunday . Thursday night also brings Trivia Night at Odeen’s at Oak Hills , while Odeen’s in Ridgefield welcomes Live Music with Cheryl & Boyd on the Porch on Fri from 5:30–8:30 PM . At FAD favorite Aquila’s Nest Vineyards , enjoy free live music Thursday through Sunday, plus Wine & Wheels on Friday . Saturday brings Radio Flashback: Your Ultimate ’70s & ’80s Rock ’n’ Roll Tribute Show at 6 PM. On Sunday, enjoy The Music of Italy with the Primavera Band at 11:30 AM, followed by Dress in White DJ Bingo at 6:30 PM. 🌍 FAD’s Event Spotlight: Fairfield International Food Fest - ConnectFairfield Looking ahead to Labor Day Weekend, the 2nd Annual Fairfield International Food Fest takes over Fairfield Theatre Company on Saturday, September 5, from 4–8 PM . Come hungry and Taste the World with pay-as-you-go global bites featuring Korean, Jamaican, Thai, Greek, Puerto Rican, British and other international flavors. Your ticket also includes three stages of entertainment , live music, cultural performances, art and family activities. Pangea Worldbeat headlines the Main Stage at 7 PM, while kids can enjoy everything from face painting and LEGO building to balloon animals, crafts and interactive activities. Guests 21+ can also visit the Tasting Mezzanine Lounge , sponsored by Elicit Brewing Co., for complimentary samples of wine, beer and spirits. 🎟️ Discounted Pre-Sale Tickets: Adults $20 | Children $10 Promo Code: CONNECT A portion of the proceeds benefits Fairfield Theatre Company . ❤️ Tuesday, August 25, 2026 New Canaan: Tuesday Night Jazz with Noreen Mola Quartet at Roger Sherman Inn(6pm - 8:30pm) ⭐🍽️Norwalk: Open Mic Night at Brass & Bone(8pm) 🎠🎪Rhinebeck, NY: Dutchess County Fair at Dutchess County Agricultural Society Inc(10am - 10pm) Rye, NY: Logical Pretzel Performs the Music of Steely Dan at Rye Town Park(7pm - 9pm) Stamford: Maria Tiscia is Rio Bound at Villa Italia Restaurant(6:30pm) ☀️🎶Stratford: Backbeat Music Outside on the Paradise Green Gazebo (7pm) ☀️🎶Trumbull: Susan Peak at Trumbull’s Summer Kids Concert Series (10-11am) ☀️🎶Trumbull: The Bernadettes at Trumbull Gazebo Tuesday Night Concert Series(7pm) Wednesday, August 26, 2026 Bethel: Mental Health Rock n' Roll Show at La Zingara Restaurant(7pm - 9:15pm) Bridgeport: Hurley Hour at BRYAC Black Rock(7pm) Bridgeport: Bingo for a Bike at BRYAC Black Rock(9pm) Danbury: Wed Open Mic at Sugar Hollow Taproom(7pm) Fairfield: Music with The Lamb Jam at The Seagrape Fairfield(8:30pm) ☀️🎶New Canaan: The Geoff Hartwell Band – Rock & Roll at Waveny Park(7:30 – 9:30pm) ⭐🎟️Newtown: Plant Bingo at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Vineyard Pilates Series by Kalia at Aquila's Nest Vineyards(6pm) Norwalk: Detroy Langer & Riccio Organ Trio at Greer Southern Table(6pm - 9pm) ⭐🍽️Norwalk: KARAOKE PARTY at Brass & Bone(8pm) ☀️🎶Norwalk: One Hot Night with Tommy Lynn at Calf Pasture Beach(7pm) Port Chester, NY: DeadCenter Mystic Dead at Garcia’s at The Capitol Theatre(8pm) Piermont, NY: John Dwyer at OTTO'S FULL SERVICE(6pm - 9pm) Pawling, NY: The Wonderwall - Tribute to Oasis at Daryl's House Restaurant & Music Club(7pm) 🎠🎪Rhinebeck, NY: Dutchess County Fair at Dutchess County Agricultural Society Inc(10am - 10pm) Shelton: Billy Solo at Spotted Horse Tavern(8pm) ☀️🎶Shelton: Kathy Thompson Band - Shelton Music under the stars Summer Concert Series (7pm) Stratford: Mike Hatfield at Joey C's Boathouse Cantina & Grill(5:30pm - 8:30pm) ☀️🎶Southbury: Eclectics - River Glen HCC Summer Concerts(6:30pm) Thursday, August 27, 2026 Bridgeport: Dale Allen at Captain's Cove Seaport (Marina, Restaurant & Bar)(5pm - 9pm) Bridgeport: Steven Capalbo at The Castle Black Rock(7pm - 10pm) Bridgeport: Bryac Funk Night Party with Friends at BRYAC Black Rock(9pm) ☀️🎶Bridgeport: Goose: Stream from Red Rocks at Twelvenote Brew Co.(9pm - 11pm) 🤠🎪🛍️Brooklyn: Brooklyn Country Fair(4pm - 11pm) Danbury: Thursday Open Jam with Sugar House at Sugar Hollow Taproom(8pm) Fairfield: Tangled Vine at The Sinclair(8:30pm) Milford: Ward Whipple at Cafe Atlantique(5pm) Milford: HAVANA NIGHT at Stonebridge Restaurant(6pm) ⭐🎟️Newtown: Tarot Reading with Abriella at Aquila's Nest Vineyards(5:30pm) ⭐🎶Newtown: Music with LT Maroon at Aquila's Nest Vineyards(5:30pm) ⭐🎟️Newtown: Yoga in the Vineyard at Aquila's Nest Vineyards(6:30pm) 🍔🍺🧠Norwalk: Trivia Night at ODEEN'S(7pm - 9pm) Pawling, NY: MACALAS at Daryl's House Restaurant & Music Club(8pm) Port Chester, NY: Real Young & Lazy Horse A Tribute to Neil Young at Garcia's at The Capitol Theatre(8pm) Ridgefield: Chris Berry & Abe Seiferth at Nod Hill Brewery(6:30pm) Redding: Bluegrass Nights at The Granite(7pm - 10pm) 🎠🎪Rhinebeck, NY: Dutchess County Fair at Dutchess County Agricultural Society Inc.(10am - 10pm) Shelton: Jack + Allie at The Gilded Whitlocks(6pm) Stratford: SHEILA & SCOTT at Blackbird's Nest(6pm) Stratford: Three Ring Circus at Joey C's Boathouse Cantina & Grill(6:30pm) Stamford: Open Mic Night at Villa Italia Restaurant(6:30pm) Stamford: West Hill Road at Columbus Park(Street Beats pop-up)(6pm - 8pm) ⭐😂🎟️Stamford: Comedian Emil Wakim at New York Comedy Club Stamford(7pm) Westport: Rale Micic at Jazz at the Post at VFW Post 399(7:30pm - 10pm) Friday, August 28, 2026 ☀️🎶Bethel: Bethel Food Truck Friday at Municipal Center Lawn (5-8pm) Bethel: Tom Duffy Band at Broken Symmetry Brew(6pm) Bethel: Good Time Charlie at Dragonfly(6pm - 9pm) Bethel: Rich Molden at Shakedown Street Eats(6:30pm) Bethel: Muddy River Blues at NOTCH8 Bar(8pm) Bedford, NY: Breakwater at Bedford Playhouse(6:30pm) ☀️🎶Brookfield: Five to One at the Summer Concerts in the Park - Brookfield (6:30pm) 🤠🎪Brooklyn: Brooklyn Fair(10am - 11pm) Bridgeport: Brett Gardner at Captain's Cove Seaport (Marina, Restaurant & Bar)(5pm - 9pm) ☀️🎶Bridgeport: Crash 21 at Twelvenote Brew Co.(7pm - 10pm) Bridgeport: Tune Squad at The Castle Black Rock(8pm - 11pm) Bridgeport: To the Max at BRYAC Black Rock(10pm) ☀️🎶Bridgeport: Take Two - Friday Night Music on the Dock at Port 5(5pm –8:30pm) 🎠🎪🛍️Chester: Chester Fair(6pm - 11pm) Danbury: Dr. Frankenbob at Charter Oak Brewing and Taproom(7pm - 9pm) Danbury: 80 vs 90s dance party at Sugar Hollow Taproom(8:30pm) Danbury: DJ Jr In The Mix at Elicit Brewing Co - Danbury(10pm) Fairfield: Jazz Fridays with Paul Bollenback Trio at Fairfield Museum(6:30pm - 8pm) Fairfield: DJ Jake Z at Elicit Brewing Co - Fairfield(10pm) Milford: Coolators at Cafe Atlantique(6:30pm) Milford: SIMPLIFY SOCIALS at Stonebridge Restaurant(9pm) New Milford: VinylCut at Housatonic River Brewing(7pm - 10pm) ⭐🎶Newtown: Music with Solid Gold Times Two at Aquila's Nest Vineyards(5:30pm - 8:30pm) ⭐🎟️Newtown: Wine and Wheels - Showcase Your Case at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Yappy Hour - Bring Your Furry Friends at Aquila's Nest Vineyards(6pm) Newtown: Bobby Morrill at NewSylum Brewing Co.(6pm - 9pm) ⭐🎟️Newtown: Charles Esten at Edmond Town Hall(8pm - 10pm) Newtown: Shay Sullivan at Perfusion Bar(8pm - 11pm) Norwalk: Tangled Vine at 314 Beer Garden(7:30pm - 11pm) ⭐🍽️ 🎶Norwalk: 'MEMBER? at Brass & Bone(9:30pm) 🎠🎪Olivebridge, NY: Summer Hoot at the Ashokan Center(3pm) Old Greenwich: Filo Fox at Bosco's Bar and Grill(9pm - 12am) Port Chester, NY: Collective Soul at The Capitol Theatre(8pm) Pawling, NY: Night of Nicks: The Stories, The Music of Stevie Nicks & Fleetwood Mac at Daryl's House Restaurant & Music Club(8pm) Port Chester, NY: What's In The Box Presented at Garcia's at The Capitol Theatre(8pm) ⭐🍽️ 🎶Ridgefield: Cheryl Ann Boyd & Co on the Porch at Odeen's BBQ(5:30pm - 8:30pm) Ridgefield: Dr. Caterwaul's Cadre of Clairvoyant Claptraps at Nod Hill Brewery(6:30pm) 🎠🎪Rhinebeck, NY: Dutchess County Fair at Dutchess County Agricultural Society Inc.(10am - 10pm) Stratford: What Up Funk at Joey C's Boathouse Cantina & Grill(9pm) ⭐😂🎟️Stamford: Comedian Rachel Feinstein at New York Comedy Club Stamford (2 shows)(7pm - 9:30pm) Stamford: Dive Bar Confessional at Third Place by Half Full Brewery(8pm - 10pm) Stamford: Bad Management at Tiernan's Bar & Restaurant(9:30pm) 🎠🎪🛍️Terryville: Terryville Lions Country Fair(4pm - 11pm) Waterbury: Chris Newell at Connecticut Distilling Tasting Lounge(5:30pm - 8:30pm) Westport: Lizzy & the Triggermen at Levitt Pavilion(7:30pm) Westport: Fake ID at Black Duck Cafe(9pm) ☀️🎶Westport: Picnic on the 4th of July - Music on Church Lane(5:30pm –9pm) Woodbury: The Rakes at Woodbury Brewing Company(8:30pm - 11pm) Saturday, August 29, 2026 Bethel: Sweet Redemption at Dragonfly(6pm - 9pm) Bethel: Sherman Hill Band at NOTCH8 Bar(8pm) Bridgeport: The Mill River Band at Captain's Cove Seaport (Marina, Restaurant & Bar)(4pm - 8pm) Bridgeport: Hurley Hour at BRYAC Black Rock(7pm) ☀️🎶Bridgeport: Round Two Acoustics at Twelvenote Brew Co.(7pm - 10pm) Bridgeport: Juliet's Run at Boca Oyster Bar(8pm - 11pm) Bridgeport: Late 4 Dinner at The Castle Black Rock(8pm - 11pm) Bridgeport: Bingo for a Bike at BRYAC Black Rock(9pm) 🤠🎪🛍️Brooklyn: Brooklyn Fair(9am - 11pm) Brookfield: Rio Sorrentino at Pulcinella(7pm - 10pm) 🤠🎪🛍️Chester: Chester Fair(8am - 11pm) Danbury: Bill Dempsey at Charter Oak Brewing and Taproom(6pm - 8pm) Danbury: Hats & Shades - A Blues Brother Tribute coming to The Palace Danbury(7:30pm) Danbury: Mx. Tiffany's GORGEOUS: an end-of-summer trans/nb takeover party! at Sugar Hollow Taproom(8:30pm) Danbury: Vivid at Elicit Brewing Co - Danbury(9pm) Danbury: DJ Tony T at Elicit Brewing Co - Danbury(10pm) Fairfield: Underdog at Fairfield's Sweet Sounds of Summer Concerts Series at Sherman Green(6:30pm) ☀️🎶Fairfield: Underdog at Fairfield's Sweet Sounds of Summer Concerts Series at Sherman Green (6:30pm) Greenwich: Chasing Romeo at Clubhouse at the Griff(7pm - 10pm) Milford: Free Music at Walnut Beach Arch(4pm –6pm) Milford: Tony Legg at Cafe Atlantique(6:30pm) Milford: STILETTO (BILLY JOEL TRIB) at Stonebridge Restaurant(5pm) ⭐🎟️New Milford: Beyond Purple at Housatonic River Brewing(7pm - 10pm) ⭐🎶Newtown: Music with The Adults Band at Aquila's Nest Vineyards(2:30pm - 5:30pm) ⭐🎟️Newtown: 70's and 80's Rock'n'Roll Tribute Show at Aquila's Nest Vineyards(6pm) Newtown: Struggle Monkey at NewSylum Brewing Co.(3pm - 6pm) Norwalk: Rodgers and Hammerstein in the Park(7pm - 8:30pm) ☀️🎶Norwalk: The Bernadettes Norwalk Summer Green Concerts (7-9pm) Norfolk: The Moonrise Cartel at Infinity Music Hall(8pm) 🎠🎪Olivebridge, NY: Summer Hoot at the Ashokan Center(3pm) Old Greenwich: Pimpinella at Bosco's Bar and Grill(9:30pm - 12am) Pawling, NY: Bowie Station - David Bowie Tribute at Daryl's House Restaurant & Music Club(8pm) Port Chester, NY: Residual Groove with Juicebox at Garcia's at The Capitol Theatre(8pm) Redding: TEN $ GRAND at Milestone(9pm) Ridgefield: Logical Pretzel at Nod Hill Brewery(5pm) 🎠🎪Rhinebeck, NY: Dutchess County Fair(10am - 10pm) Shelton: Tangled Vine at Spotted Horse Tavern(8pm) Shelton: Music by Hype at Pier131 Kitchen + Bar(9:30pm - 12am) Sherman: James Taylor & Carole King Musical Tribute with Unbroken Glass & Friends at JCC in Sherman(7;30pm - 9:30pm) Stratford: BILLY GENUARIO at Blackbird's Nest(6pm) Stratford: FLANNEL CLAD MASSES at Blackbird's Nest(6pm) Stratford: Hop Yard Concert Series Featuring The Tony Ferrigno Trio at Two Roads Brewing Company(6pm - 8pm) Stratford: Zac N' Friends at Joey C's Boathouse Cantina & Grill(9pm) ⭐😂🎟️Stamford: Comedian Rachel Feinstein at New York Comedy Club Stamford (2 shows)(7pm - 9:30pm) Stamford: The Proper Villains at Tiernan's Bar & Restaurant(9:30pm) 🎠🎪🛍️Terryville: Terryville Lions Country Fair(9am - 11pm) Westport: Billy & the Showmen at Levitt Pavilion(7:30pm) Westport: The Zambonis at Walrus Alley(7:30pm - 10:30pm) Westport: Vertigo at Black Duck Cafe(9pm) ☀️🎶Westport: Steve Keith - Music on Church Lane(5:30pm –9pm) Woodbury: Almost Elton at Woodbury Brewing Company(8:30pm - 11pm) Sunday, August 30, 2026 Bethel: Jazz Brunch - Dirty Martins at Shakedown Street Eats(12pm) Bethel: Shay Sullivan at Broken Symmetry Brew(12pm) Bethel: Sister Funk at NOTCH8 Bar(5pm) Bethel: Cross Purpose on the Bethel Municipal Lawn(6pm - 8pm) ☀️🎶Bridgeport: Awen Family Band at Twelvenote Brew Co.(2pm - 5pm) Bridgeport: Frank Yantorno at The Castle Black Rock(5pm - 8pm) Bridgeport: Riley Johnson at BRYAC Black Rock(6pm) Bridgeport: Bryac Funk Night Party with Friends at BRYAC Black Rock(9pm) ☀️🎶Bridgeport: Bad Saints Stripped - Sunday Night Music on the Dock at Port 5(3pm) Bridgeport: To The Max at Captain's Cove Seaport (Marina, Restaurant & Bar)(3pm - 7pm) Brooklyn: Brooklyn Fair(9am - 6pm) Chester: Chester Fair(9am - 6pm) Danbury: SwingSet at Charter Oak Brewing and Taproom(3pm - 5pm) Danbury: The Jones Factor at Molly Darcy’s Irish Pub & Restaurant(6pm) ☀️🎶Greenwich: Sound Beach Community Band - Wicked Good: The Music of Stephen Schwartz at Binney Park (7pm) ☀️🎶Milford: Dr. B and the Remedy - Walnut Beach Pavillion(4pm –7pm) Milford: NASHVILLE NIGHT W/ HAZZARD COUNTY at Stonebridge Restaurant(4pm) ⭐🎶Newtown: The Music of Italy Band Show at Aquila's Nest Vineyards(11:30pm) ⭐🎟️Newtown: Girl Scout Cookies & Wine Pairing at Aquila's Nest Vineyards(12pm) ⭐🎟️Newtown: Music with On The Road Again at Aquila's Nest Vineyards(2pm - 5pm) ⭐🎟️Newtown: Dress in White DJ Bingo at Aquila's Nest Vineyards(6:30pm) Newtown: One Level Down at NewSylum Brewing Co.(2pm - 5pm) Newtown: Jailhouse at Reverie Brewing Company(2pm - 5pm) Norwalk: Matt Fernandez at Washington Prime(12pm - 3pm) Norwalk: Bad Mannerz at 314 Beer Garden(3pm - 6pm) Norwalk: Damn Tall Buildings | The Cody Sisters at Pinkney Park(5:30pm - 8pm) 🎠🎪Olivebridge, NY: Summer Hoot at the Ashokan Center(3pm) Pawling, NY: Thurston Howell – A Premier Yacht Rock Spectacular at Daryl's House Restaurant & Music Club(7pm) Piermont, NY: Piano Brunch Sunday at OTTO'S(12pm - 3pm) ☀️🎶Redding: Bookends at The Redding Town Green (6-8pm) Redding: Bookends at Redding Town Green(6pm - 8pm) Redding: On the Count of Two Jazz Quartette at Milestone(4pm) 🎠🎪Rhinebeck, NY: Dutchess County Fair(10am - 8pm) Shelton: Sunday Jazz Series at The Gilded Whitlocks(2pm - 5pm) Shelton: Johnny Banannas at Pier131 Kitchen + Bar(6:30pm - 9pm) Shelton: Billy G Band at Spotted Horse Tavern(8pm) Stratford: Hop Yard Concert Series Featuring Whabendos at Two Roads Brewing Company(2pm - 4:30pm) Stratford: SHOT DOWN at Blackbird's Nest(4pm) Stamford: Honey Harvest Festival at Bartlette Arboretum & Gardens(11am - 4pm) ⭐😂🎟️Stamford: Comedian Juston McKinney at New York Comedy Club Stamford(7pm) 🎠🎪🛍️Terryville: Terryville Lions Country Fair(9am - 6pm) Westport: Tim Palmieri at Walrus Alley(5pm - 8pm)