FAD’s Hot Picks for Oktoberfest Happenings In and Around Fairfield County

Love shopping small and discovering something you won’t find everywhere else? PopShop Market is bringing its popular curated artisan markets to Fairfield, Darien, Westport and Milford throughout the rest of 2026. PopShop isn’t your typical vendor fair. Each market features a carefully curated, hand-picked selection of artisans, makers, designers, boutiques and small businesses , offering everything from clothing and jewelry to home décor, specialty goods, self-care products and unique gifts. 🛍️ Save the Dates! DARIEN — Darien Commons 📅 September 19 • October 17 • November 21 FAIRFIELD — Elicit Brewing Co. 📅 September 27 • November 22 • December 6 WESTPORT — Westport Museum for History & Culture 📅 October 3 • November 15 MILFORD — Historic Milford Green 📅 November 7 With the holiday season approaching, PopShop is a great place to shop small, support local and find one-of-a-kind gifts while meeting some of the talented people behind the products. The best part? Every PopShop is different. The vendor lineup changes from market to market, so there’s always something new to discover. Grab a friend, make a day of it and see what catches your eye! SHOP SMALL 💛 SUPPORT LOCAL 💛 DISCOVER THE UNIQUE!

This week, Fairfield After Dark is giving a special shout-out to Beth-El Center in Milford as they get ready for their big Benefit Concert featuring The Yacht Lobsters this Friday, September 11! Get ready for an evening of smooth yacht rock while supporting an important local cause. Proceeds from the concert will help Beth-El Center provide vital services to individuals and families experiencing homelessness. 🎶 The Yacht Lobsters Benefit Concert 📅 Friday, September 11 📍 Milford Veterans Memorial Auditorium, Milford, CT 🚪 Doors Open: 7 PM | Show: 8 PM 🎟️ Tickets start at $29 — Purchase Tickets Here: https://bit.ly/3TlcjeK Great music. A great night out. An even greater cause. Can’t make the show? Consider making a donation to Beth-El Center and helping support individuals and families in our community who need a helping hand. As Outdoor Summer Concert Series begin winding down throughout Fairfield County , we can officially say Summer 2026 was one for the books! Great concerts, incredible shows, fantastic festivals, and plenty of memorable summer nights. But the fun isn't slowing down— fall events are kicking into gear, and the calendar is filling up fast! Whether you're looking for something to do today, tomorrow, or this weekend , Fairfield After Dark makes it easy to see what’s happening throughout the area. Check back every day for the latest happenings and plan your weekend early with our updated lineup of concerts, festivals, fairs, live music, comedy, theater, and more. There’s always something happening in Fairfield County and beyond— so check out this week’s list and start making plans! Wednesday, September 9, 2026 Bridgeport: Hurley Hour LIVE at BRYAC Black Rock(7pm) Bridgeport: Bingo for a Bike LIVE at BRYAC Black Rock(9pm) Danbury: Wed Open Mic LIVE at Sugar Hollow Taproom(7pm) Fairfield: Music with The Lamb Jam at The Seagrape Fairfield(8:30pm) ⭐🎟️Newtown: FREE Mahjong Open Play at Aquila's Nest Vineyards(5pm) ⭐🎟️Newtown: Pilates in the Vineyard. with Lauren Mika at Aquila's Nest Vineyards(6:30pm) ⭐🎟️Newtown: Speed Dating Ages 40-55 at Aquila's Nest Vineyards(7pm) Norwalk: Detroy Langer & Riccio Organ Trio at Greer Southern Table(6pm - 9pm) Thursday, September 10, 2026 Bridgeport: Bryac Funk Night / Party with Friends LIVE at BRYAC Black Rock(9pm) Bridgeport: Jason Heffernan LIVE at The Castle, Black Rock(7pm - 10pm) Danbury: Thursday Open Jam with Sugar LIVE at Sugar Hollow Taproom(8pm) Fairfield: Some Hacks LIVE at The Sinclair(8:30pm) 🎪🛍️Hebron: Hebron Harvest Fair(4pm - 10:30pm) Milford: Pete Grossi LIVE at Cafe Atlantique(5pm) ⭐🎟️Newtown: Don Lowe LIVE at Aquila's Nest Vineyards(5:30pm) ⭐🎟️Newtown: A Golden Hour Yoga Experience at Aquila's Nest Vineyards(6pm) 🎪🛍️North Haven: North Haven Fair(5pm - 10pm) 🍔🍺🧠Norwalk: Trivia Night at ODEEN'S(7pm - 9pm) Port Chester, NY: An Evening with Phunk & Roses LIVE at Garcia's at The Capitol Theatre(8pm) 🎪🛍️South Windsor: Wapping Fair(5pm - 10pm) Shelton: Jack + Allie at The Gilded Whitlocks(6pm) Stratford: TONY MAC LIVE at Blackbird's Nest(5pm) ⭐😂🎟️Stamford: That's Fair Comedy ft: Connor O'Brien, Dan Kalwhite, Chris Warren, Joe Russell, Cody Marino at New York Comedy Club Stamford(7pm) Westport: Janice Friedman LIVE at Jazz at the Post at VFW Post 399(7:30pm - 10pm) Friday, September 11, 2026 Bethel: AL RIVOLI LIVE at Whitlock’s Restaurant(6pm - 9pm) Bethel: Mike and Ike LIVE at DragonFly(6pm - 9pm) Bethel: Erik Rabasca LIVE at Shakedown Street Eats(6:30pm - 9:30pm) ☀️🎶Bridgeport: Hesitation Blues Band LIVE at Twelvenote Brew Co.(7pm - 10pm) Bethel: Black Rock Blues LIVE at Notch8 Bar(8pm) Bridgeport: Black Ties & Bourbon LIVE at Boca Oyster Bar(8pm - 11pm) Bridgeport: Herman & Company LIVE at The Castle, Black Rock(8pm - 11pm) ☀️🎶Bridgeport: Gab Kallay - Friday Night Music on the Dock at Port 5(5pm –8:30pm) 🎪🛍️Bethlehem: Bethlehem Fair(5pm - 10pm) Bridgeport: Fake ID LIVE at Boca Oyster Bar(3pm - 6pm) Danbury: DJ Jake Z LIVE at Elicit Brewing Co - Danbury(10pm) Danbury: Tangled Vine w/ Classic Waze LIVE at Sugar Hollow Taproom(8pm) 🎪🛍️Hebron: Hebron Harvest Fair(12pm - 12am) New Milford: ShineBox (Formerly The Winnie Shins) LIVE at Housatonic River Brewing(7pm - 10pm) ⭐🎟️Newtown: John Shavers LIVE at Aquila's Nest Vineyards(5:30pm - 8:30pm) ⭐🎟️Newtown: Girl Scout Cookies & Wine Pairing at Aquila's Nest Vineyards(6pm) ⭐🎟️Newtown: Speed Dating Ages 35-49 at Aquila's Nest Vineyards(7pm) Newtown: Tom Ardise LIVE at Perfusion Bar(8pm - 11pm) 🎪🛍️North Haven : North Haven Fair(3pm - 11pm) Norwalk: The Bernadettes LIVE at 314 Beer Garden(7:30pm - 10:30pm) ⭐🍽️ 🎶Norwalk: Skunk Rockets LIVE at Odeen's Oak Hills(7pm - 10pm) 🎪Norwalk: Norwalk Oyster Festival at Veteran's Memorial Park(6pm - 11pm) Norwalk: Pimpinella LIVE at Sails American Grill(9pm - 12am) Redding: Bone Dry LIVE at The Redding Roadhouse(7pm - 10pm) Ridgefield: Dr. B and the Remedy LIVE at Nod Hill Brewery(6:30pm) 🎪🛍️South Windsor: Wapping Fair(5pm - 11pm) Stratford: DAVE + CRISSY ACCOUSTIC LIVE at Blackbird's Nest(6pm) Stratford: Suckr' Punch LIVE at Windmill Tavern(8pm) Stratford: The Rajsaan Langley Project LIVE at Joey C's Boathouse Cantina & Grill (9pm) ⭐😂🎟️Stamford: Comedian Jiaoying Summers at New York Comedy Club Stamford (4 shows)(7pm - 9:30pm) Stamford: Nothing Serious LIVE at Tiernan's Bar & Restaurant(9:30pm) Stamford: That’s What She Said LIVE at Third Place by Half Full Brewery(8pm - 10pm) Westport: Not My Problem LIVE at Black Duck Cafe(9pm) Westport: MASSIVE DIVA LIVE at Walrus Alley(7:30pm - 10:30pm) ☀️🎶Westport: Steve Keith - Music on Church Lane(5:30pm –9pm) Woodbury: Iris Lies LIVE at Woodbury Brewing Company(8:30pm - 11pm) Saturday, September 12, 2026 Bethel: Al Rivoli LIVE at Shakedown Street Eats(6:30pm - 9:30pm) Bethel: Jake Kulak LIVE at Notch8 Bar(8pm) 🎪🛍️Bethlehem: Bethlehem Fair(8am - 10pm) Brookfield: Rio Sorrentino LIVE at Pulcinella(7pm - 10pm) ☀️🎶Bridgeport: Harborfest W/Tangled Vine (Saturday) - Sunday Night Music on the Dock at Port 5(3pm) Bridgeport: Black Rock Harbor Fest(7pm) ☀️🎶Bridgeport: The Doctors' Jones LIVE at Twelvenote Brew Co.(7pm - 10pm) Bridgeport: Havana Night LIVE at Captain's Cove Seaport (Marina, Restaurant & Bar)(8pm - 12am) Bridgeport: Red Bull Express LIVE at The Castle, Black Rock (8pm - 11pm) Bridgeport: C-Sides LIVE at BRYAC Black Rock(10pm) Danbury: Bryan Bielanski LIVE at Charter Oak Brewing and Taproom(4pm - 6pm) Danbury: The Proper Villains LIVE at Elicit Brewing Co - Danbury(9pm) Danbury: DJ Ilardi LIVE at Elicit Brewing Co - Danbury(10am) Danbury: Breath w/Entrance LIVE at Sugar Hollow Taproom(8pm) Danbury: HIJACKED LIVE at Molly Darcy’s Irish Pub & Restaurant(11pm) 🎪🛍️Hebron: Hebron Harvest Fair(10am-12am) Milford: Matt Popp LIVE at Cafe Atlantique(6:30pm) New Milford: Nashville Drive LIVE at Housatonic River Brewing(7pm - 10pm) New Canaan: MIND THE GAP LIVE at Gates Restaurant + Bar(8:30pm) ⭐🎟️Newtown: Slumber Party Drag Bingo at Aquila's Nest Vineyards(12pm) ⭐🎟️Newtown: Tony & The West Siders LIVE at Aquila's Nest Vineyards(2:30pm - 5:30pm) ⭐🎟️Newtown: Cuboricua Salsa Band Show at Aquila's Nest Vineyards(6pm) Newtown: The Barn Rats LIVE at NewSylum Brewing Co.(3pm - 6pm) Newtown: Emma Henning LIVE at Perfusion Bar(8pm - 11pm) 🎪🛍️North Haven: North Haven Fair(10am-11pm) 🎪Norwalk: Norwalk Oyster Festival at Veteran's Memorial Park(11am-11am) ⭐🍽️ 🎶Norwalk: Gray Rock Band LIVE at Odeen's Oak Hills(7:30pm - 10:30pm) Norwalk: Ron Wilson LIVE at Sails American Grill(9pm - 12am) Old Greenwich: Liquid Courage LIVE at Bosco's Bar and Grill(9pm - 12am) Port Chester, NY: A Farewell to Kings - Rush Tribute LIVE at Garcia's at The Capitol Theatre(8pm) Redding: Fuzz LIVE at Milestone(9pm - 11:30pm) Ridgefield: The Oktoberfest Band LIVE at Nod Hill Brewery(1pm) Ridgefield: Liz Ashkins LIVE at Nod Hill Brewery(5pm) 🎪🍷🍔Rhinebeck, NY: Hudson Valley Wine & Food Festival(11am - 6pm) 🎪🛍️South Windsor: Wapping Fair(10am-11pm) Shelton: Dj Nate LIVE at Pier131 Kitchen + Bar(9:30pm - 12am) Stratford: RYAN COLLINS LIVE at Blackbird's Nest(6pm) ⭐😂🎟️Stamford: Comedian Jiaoying Summers at New York Comedy Club Stamford (4 shows)(7pm - 9:30pm) Stamford: Get Lit LIVE at Tiernan's Bar & Restaurant(9:30pm) Stamford: Taste of Egypt - Egyptian Festival(12pm - 6pm) Stamford: TEN $ GRAND LIVE at Third Place by Half Full Brewery(7pm - 10pm) Tarrytown, NY: MH Studio: Bill Kelly LIVE at Tarrytown Music Hall(7:30pm) Westport: Old Bob LIVE at Walrus Alley(7:30pm - 10:30pm) ☀️🎶Westport: TBA - Music on Church Lane(5:30pm –9pm) Woodbury: KISS Alive! NYC LIVE at Woodbury Brewing Company(8:30pm - 11pm) Sunday, September 13, 2026 Bethel: Rob Glassman Duo - 3pm Dead Set LIVE at Shakedown Street Eats(3pm - 6pm) Bethel: Exit 5 LIVE at Notch8 Bar(5pm) 🎪🛍️Bethlehem: Bethlehem Fair(8am - 5:30pm) ☀️🎶Bridgeport: The Signature Duo - Sunday Night Music on the Dock at Port 5(3pm) Bridgeport: SHAMELESS LIVE at Captain's Cove Seaport (Marina, Restaurant & Bar)(3pm - 7pm) ☀️🎶Bridgeport: Jared Sage Cowen LIVE at Twelvenote Brew Co.(2pm - 5pm) Bridgeport: Free Form Filth LIVE at BRYAC Black Rock(6pm) Bridgeport: Joey Whelan LIVE at The Castle, Black Rock(5pm - 8pm) Danbury: Mosaic Jazz Quartet LIVE at Charter Oak Brewing and Taproom(2pm - 4pm) Danbury: Jim Lapine LIVE at Molly Darcy’s Irish Pub & Restaurant(6pm) 🎪🛍️Hebron: Hebron Harvest Fair(10am - 7:30pm) Milford: Shilelagh Law at Stonebridge Restaurant(2pm) Newtown: Jeff Summa & the Roasters LIVE at Newsylum Brewing(2pm - 5pm) ⭐🎟️Newtown: Bobby Wheeler LIVE at Aquila's Nest Vineyards(2:30pm - 5:30pm) ⭐🎟️Newtown: Andrea Bocelli Tribute at Aquila's Nest Vineyards(6pm) 🎪🛍️North Haven: North Haven Fair(10am - 7pm) Norwalk: The Last Hoorah LIVE at 314 Beer Garden(3pm - 6pm) 🎪Norwalk: Norwalk Oyster Festival at Veteran's Memorial Park(11am - 8pm) Norwalk: Christopher Brown LIVE at Washington Prime(12pm - 3pm) ⭐🍽️ 🎶Norwalk: Pat Lavery Band LIVE at Odeen's Oak Hills(7:30pm - 10:30pm) ☀️🎶Old Greenwich: Jamie McClean Band - Greenwich Point Summer Concerts(4pm) Piermont, NY: Piano Brunch Sunday at OTTO'S(12pm - 3pm) Redding: Fake ID Duo LIVE at Milestone(4pm) 🎪🍷🍔Rhinebeck, NY: Hudson Valley Wine & Food Festival(11am - 5pm) Shelton: Sunday Jazz Series at The Gilded Whitlocks(2pm - 5pm) Shelton: Ferigno Band LIVE at Spotted Horse Tavern(8pm) Shelton: DJ Revuelo LIVE at Pier131 Kitchen + Bar(11:30am - 3:30pm) 🎪🛍️South Windsor: Wapping Fair(10am - 6pm) 🎪🎷Stratford: Latin Music Festival(10am) Stratford: WHAT UP FUNK LIVE at Blackbird's Nest(4pm) Stratford: Tangled Vine LIVE at Joey C's Boathouse Cantina & Grill(3pm - 7pm) ⭐😂🎟️Stamford: Comedian Katie Boyle at New York Comedy Club Stamford(7pm) Stamford: Taste of Egypt - Egyptian Festival(12pm - 6pm) Westport: Hitch Trio LIVE at Walrus Alley(12pm - 3pm) Woodbury: The Michael Allman Band w/sg Greg Mattson LIVE at Woodbury Brewing Company (5pm - 9pm)

Fairfield, CT: The Moonrise Cartel brings their signature Folk Rock from Black Rock to The Warehouse at FTC on October 10 for a must-see hometown show.

Milford, CT: Yacht Lobsters bring the ultimate yacht rock party to Milford Sept. 11 for a benefit concert supporting Beth-El Center.

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)