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Labor Day Week-End Family Fun Guide: Top 5 Picks & more!
Labor Day Week-End Family Fun Guide: Top 5 Picks August 27 - September 1
Labor Day is almost here, and Fairfield County (plus surrounding towns) is packed with family-friendly events to enjoy before summer officially winds down. From classic New England fairs 🎡 to wildlife encounters 🐅, live music 🎶, and food fests 🍴, there’s something happening every single day. We’ve rounded up the Top 5 Family Fun Picks each day to help you plan your week.
Sponsor Spotlight: ConnectFairfield
We’re thrilled to feature ConnectFairfield as this week’s sponsor—proud host of the inaugural Fairfield International Food Festival at Fairfield Theatre Company on Saturday, August 30. ConnectFairfield curates' experiences that unite neighbors, businesses, and nonprofits. From hands-on culinary fundraisers to cultural celebrations and local arts events, their gatherings reflect the town’s spirit—while giving back. A portion of this festival’s proceeds support Operation Hope, continuing their tradition of community care in Fairfield.
About ConnectFairfield
ConnectFairfield, founded in 2021 by Debbi O’Keefe, is a community platform dedicated to hosting events that connect residents, businesses, and nonprofits in the town of Fairfield.
With 30+ years of event planning experience, Debbi uses her local ties to strengthen Fairfield’s community spirit. ConnectFairfield produces cultural festivals, fundraisers, and interactive gatherings that bring neighbors together, while donating a portion of proceeds to local nonprofits such as Operation Hope.
Wednesday, Aug 27 – Outdoor Music & Family Nights
🎡
St. Leo’s Fair (Stamford, 6pm–10pm)
The rides, food, and family fun continue.
🎶
ROYAL KINGS at Waveny Park Summer Concert (New Canaan, 7:30pm–9:30pm)
Free live music under the stars — bring a blanket and snacks.
🎼
The Bernadettes – Music Under the Stars (Shelton, 7pm)
A family dance-along favorite!
🧩
Open Play Chess at Veterans Park (Stamford, 12pm–2pm)
A fun mix of strategy, fresh air, and community.
🐾
Zoo & Treesure Hunt Combo (Bridgeport/Norwalk)
Perfect daytime adventures before the music begins.
📣 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)
Bethel: "Nothing But The Blues" LIVE at La Zingara Restaurant(7pm)
Fairfield: Mixtape Match Musical Bingo at Elicit Brewing(7pm)
Norwalk: Norwalk’s Treesure Hunt(7am-7pm)
📣 Newtown: Meditation on Twin Hearts at Aquila's Nest Vineyards(7pm)
New Canaan: ROYAL KINGS at Waveny Park (7:30pm-9:30pm)
Stamford: Open Play Chess in Veterans Memorial Park – Stamford(12pm-2pm)
Stamford: St. Leo's Fair(6pm-10pm)
📣 Stamford: History Hyenas w/ Chris Distefano & Yannis Pappas at New York Comedy Club Stamford(7pm)
Shelton: The Bernadettes at Music Under the Stars Summer Concert Series(7pm)
Thursday, Aug 28 – Fairs, Culture & History
🎡
St. Leo’s Fair (Stamford, 6pm–11pm)
A Labor Day week tradition for many families.
🐅
Beardsley Zoo + Skyhunters (Bridgeport, all day)
A great daytime activity before heading to evening fun.
🎪
Woodstock Fair – 164th Annual Kickoff (Woodstock, 4pm–9:30pm)
A classic agricultural fair with rides, food, and livestock — New England tradition at its best.
🎨
Summer Thursdays at Weston History & Culture Center (1pm–4pm)
Kid-friendly hands-on activities mixed with local history.
🎶
Outdoor Family-Friendly Music Across Fairfield County
Multiple towns host live music — an easygoing family night out.
📣 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)
Bridgeport: Hurley Hour LIVE at Bryac Black Rock(6pm)
Bridgeport: Chris Radz LIVE at The Castle(7pm-10pm)
Danbury:Line Dancing at Elicit Danbury(7pm)
📣 Fairfield: Jake Shimabukuro in The Warehouse at FTC(8pm)
Fairfield: Suck'R Punch LIVE at The Sinclair(8:30pm)
Milford: Young Dan & Jumpin Johnny LIVE at Cafe Atlantique(5pm-8pm)
Milford: HAVANA NIGHT LIVE at Stonebridge Restaurant(6pm)
Norwalk: Steven Keith at BANC House (5:30-8:30pm)
Norwalk: Norwalk’s Treesure Hunt(7am-7pm)
Norwalk: Mike Millazo at Sails Bar & Grill
Norwalk: Party with Friends LIVE at Washington Social(8pm-11:30pm)
📣 Newtown: Glen Roth LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm)
📣 Newtown: Tarot Reading with Jenny Gypsy at Aquila's Nest Vineyards(5:30pm-9pm)
📣 Piermont, NY: Live Jazz with Trumpet: Antoine Drye & Pianist: Kevin Lovejoy at OTTO'S(6pm-9pm)
Rowayton: Mike Millazo LIVE at Sails Bar & Grill(6pm-9:30pm)
Stamford: St. Leo's Fair(6pm-11pm)
Stamford: Karaoke with T.A.N. BAND LIVE at Half Full Brewery(8pm-10pm)
📣 Stamford: That's Fair Comedy ft: Cody Marino, Brittany Brave, Nikhill Mehta, Chris Kinback, Trent Mabry at New York Comedy Club Stamford(7pm)
Stratford: Dawn & Greg LIVE at Outriggers(5pm-8pm)
Stratford: The Groove Grove Band LIVE at Joey C’s Boathouse(6pm-9pm)
Weston: Summer Thursdays at Weston History & Culture Center(1pm-4pm)
Westport: Live music with Billy Genuario(9pm)
Woodstock: Woodstock Fair - 164th Annual Fair!(4pm-9:30pm)
🎪 Friday, Aug 29 – Fairs & Outdoor Concerts
🎡
St. Leo’s Fair (Stamford, 6pm–9pm)
Friday night rides and lights!
🐾
Beardsley Zoo (Bridgeport, all day)
Always a top family adventure.
🎠
Haddam Neck Fair (East Hampton, opens 3pm)
A long-running fair with rides, farm animals, and fireworks.
🎭
Woodstock Fair (Woodstock, 12pm–9:30pm)
Day two of one of CT’s largest agricultural fairs.
🎶
Free Outdoor Concerts (Brookfield, Bethlehem, Fairfield & more)
Pack a picnic and enjoy a community night out with music.
Bethel: John Fazio Jr LIVE at Broken Symmetry(6pm)
Bethel: BRANDON MULLIS LIVE at Shakedown Street Eats(6:30pm)
Bethel: FIVE TO ONE Live at Notch 8(8pm)
📣 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)
Bridgeport: The Two J's at Port 5(5-8:30pm)
Bridgeport: Scratch Band LIVE at The Castle(8pm-11pm)
Bridgeport: TBA LIVE at Bryac Black Rock(10pm)
Bethlehem: The Rakes at Friends Friday Summer Concerts at March Farm(6-8pm)
Brookfield: Dan’s Garage LIVE at Brookfield's Concerts in the Park(6:30 PM)
Danbury: Zach Anderson LIVE at Charter Oak Brewing(7pm-9pm)
Danbury: DERT LIVE at Sugar Hollow Taproom(8:30pm)
Danbury: Vivid LIVE at Elicit Danbury(9pm)
East Hampton: Haddam Neck Fair(3pm)
Fairfield: Jazz Fridays w/Chris Coogan at Fairfield Museum(6:30pm-8pm)
Fairfield: Black Rock Fire LIVE at Elicit Brewing(9pm)
Fairfield: DJ Durso in the Speakeasy LIVE at Elicit Brewing(10pm)
Greenwich: TNT Band LIVE at Griff Club House(7pm-10pm)
Milford: Handpan Concert – Spirit Voices 2(7:30pm-9:30pm)
Milford: RECKLESS SUNSET LIVE at Stonebridge Restaurant(5:30pm)
Milford: Lindsey & Shelley LIVE at Cafe Atlantique(6:30pm-9:30pm)
New Milford: Lost Rebel LIVE at Housatonic River Brewing(7pm-10pm)
Norwalk: Live Music With Geoff Hartwell(10pm)
Norwalk: Norwalk’s Treesure Hunt(7am-7pm)
Norwalk: Pimpinella - LIVE at the Sand Bar(8pm-11pm)
Norwalk: Tom Petty Night LIVE at Washington Social(8pm-11:30pm)
Norwalk: Tangled Vine - LIVE at SOHO bar(9pm)
Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm)
Newtown: Blimp Fest 2025: Case Galv & Code, Drink Baby, & Atlas AltaLIVE at Reverie Brewing(6:30pm-10pm)
📣 Newtown: Bobby Wheeler LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm)
📣 Newtown: Belgian Chocolate and Wine Pairing at Aquila's Nest Vineyards(6pm)
📣 Newtown: Baked Brie & Vino Nights at Aquila's Nest Vineyards(6:30pm)
📣 Newtown: Yappy Hour - Bring Your Furry Friends at Aquila's Nest Vineyards(6pm)
📣 Newtown: The Lightfoot Band at Edmond Town Hall(8pm)
Newtown: Orb Mellon LIVE at Perfusion(8pm-11pm)
Newtown: ETH DRIVE-IN: Dirty Dancing (PG-13)(9pm)
Old Greenwich: Dad Bod Band LIVE at Bosco's Bar & Grill(9pm-11:30pm)
Orange: GREEK FESTIVAL – St. Barbara (12pm-10pm)
Redding: Jonny Chapman Trio LIVE at The Redding Roadhouse(7pm-10pm)
Ridgefield: Phil & Isabel LIVE at Odeen’s Restaurant(5:30pm)
Ridgefield: Live Music with Corey Lewin at 850 Degree(6pm-9pm)
Ridgefield: Nathaniel Hintz LIVE at Nod Hill Brewery(6:30pm)
Rowayton: Not My Problem LIVE at Sails Bar & Grill(9:30pm-12am)
Shelton: Riley Johnson at Jones Winery(5–7pm)
📣 Stamford: That's Fair Comedy at New York Comedy Club Stamford(9:30pm)
Stamford: St. Leo's Fair(6pm-9pm)
Stamford: Dive Bar Confessional LIVE at Half Full Brewery(7pm-9pm)
📣 Stamford: Comedian Troy Bond at New York Comedy Club Stamford(7pm-9:30pm)
Stratford: Live Music with No Strings Attached at Windmill Tavern(5pm)
Stratford: Frank Chiafari LIVE at Outriggers(5:30pm-8;30pm)
Stratford: Stairway to Halen LIVE at Joey C’s Boathouse(9pm-12am)
Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm)
Woodbury: Macalas LIVE at Woodbury Brewing Company(8:30pm)
Woodstock: Woodstock Fair - 164th Annual Fair!(12pm-9:30pm)
📣 Westport: Picnic on the 4th of July at Music on Church Lane(6pm-9pm)
Westport: Union Rail LIVE at Walrus Alley(7:30pm-11pm)
Westport: Shell Shockt LIVE at Black Duck Cafe(9:30pm)
Saturday, Aug 30 – Festivals & Fairs Galore
🍴
Fairfield International Food Fest at FTC (Fairfield, 4pm)
A global food adventure with live music and entertainment — perfect for families with adventurous eaters.
🎠
Haddam Neck Fair (East Hampton, 3pm)
Tractor pulls, rides, and fireworks make this a highlight of the weekend.
🏰
Connecticut Renaissance Faire – Opening Weekend (Lebanon, 10:30am–6pm)
Step back in time with jousting, costumed performers, and themed family fun.
🎡
St. Leo’s Fair (Stamford, 2pm–11pm)
A full day of rides, games, and food — kids’ favorite stop of the week.
🐅
Beardsley Zoo + Skyhunters (Bridgeport, 10am–2pm)
Perfect for a morning family outing before hitting the fairs.
Bethel: MUDDY RIVER BLUES Live at Notch 8(8pm)
📣 Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)
📣 Bridgeport: Skyhunters in Flight at Connecticut's Beardsley Zoo(11am-2pm)
Bridgeport: Acoustic Mafia LIVE at Boca Oyster Bar(5pm)
Bridgeport: Ryan Collins LIVE at The Castle(8pm-11pm)
Bridgeport: Sneaky Pete LIVE at Bryac Black Rock(9:30pm)
Danbury: The Light w/Atom Rush LIVE at Sugar Hollow Taproom(8:30pm)
Danbury: Get Lit LIVE at Elicit Brewing(9pm)
East Hampton: Haddam Neck Fair(3pm)
Fairfield: El Camino LIVE at Sherman Green Gazebo(6:30-8:00 PM)
Fairfield: Movie Day - featuring Alice in Wonderland (Live Action)! at Elicit Brewing(1pm)
📣 Fairfield: Fairfield International Food Fest at FTC(4pm)
Fairfield: DJ DONNY D in the Speakeasy LIVE at Elicit Brewing(10pm)
Fairfield: El Camino LIVE at Sherman Green Gazebo(6:30pm-8pm)
Lebanon: 27th Annual Connecticut Renaissance Faire(10:30am-6pm)
Milford: STILETTO (BILLY JOEL TRIBUTE) LIVE at Stonebridge Restaurant(5pm)
Milford: Bob Gotta LIVE at Cafe Atlantique(6:30pm-9:30pm)
New Milford: Street Survivors - Tribute to Lynyrd Skynyrd LIVE at Housatonic River Brewing(7pm-10pm)
Norwalk: Norwalk’s Treesure Hunt(7am-7pm)
Norwalk: SoNo Saturday Market(10am-1pm)
Norwalk: What Up Funk Band LIVE at 314 Beer Garden(7:30pm-10:30pm)
Norwalk: The Last Hoorah LIVE at Washington Social(8pm-11:30pm)
📣 Newtown: Mini Cheesecakes & Sweet Wines Pairing at Aquila's Nest Vineyards(12pm)
📣 Newtown: Frandango LIVE at Aquila's Nest Vineyards(2:30pm-5:30pm)
📣 Newtown: I Love the 80s to Death Murder Mystery at Aquila's Nest Vineyards(6pm)
Newtown:Seth Adam LIVE at Newsylum Brewing Co(3pm-6pm)
Newtown: Eric Christensen LIVE at Perfusion(8pm-11pm)
📣 Newtown: ETH DRIVE-IN: Dirty Dancing (PG-13)(9pm)
Orange: GREEK FESTIVAL – St. Barbara (12pm-10pm)
Redding: Pimpinella LIVE at Milestone(9pm-12am)
Ridgefield: Live Music with Don Lowe at 850 Degree(6pm)
Ridgefield: The Last Minutemen LIVE at Nod Hill Brewery(6:30pm)
Stamford: Open Play Chess in Latham Park – Stamford(1pm-3pm)
Stamford: Outsyders LIVE at Half Full Brewery(2pm-5pm)
Stamford: St. Leo's Fair(2pm-11pm)
Stamford: Cobblestone Road at The Beer Garden (Shippan Landing)(5pm-8pm)
📣 Stamford: Comedians Meka Mo, Adam Muller, JC Mendoza, Brendan Sagalow at New York Comedy Club Stamford(4:30pm)
📣 Stamford: Comedian Troy Bond at New York Comedy Club Stamford(7pm-9:30pm)
Stamford: Superhero LIVE at Tigín Irish Pub(10pm)
Stratford: Dawn & Greg LIVE at Outriggers(5:30pm-8:30pm)
Stratford: Zac & Fried LIVE at Joey C’s Boathouse(9pm-12am)
Shelton: SOME HACKS at Pier 131 Kitchen(9:30pm)
Woodstock: Woodstock Fair - 164th Annual Fair!(12pm-9:30pm)
Westport: Vinnie Ferrone at Music on Church Lane(6pm-9pm)
Westport: Massive Diva LIVE at Walrus Alley(7:30pm-11pm)
Westport: Sucker Punch LIVE at Black Duck Cafe(9:30pm)
Woodbury: Second Nature LIVE at Woodbury Brewing Company(8:30pm)
Milford: Rum Runners at Walnut Beach Pavillion(4-7pm)
📣 Newtown: Summer Lovin' Drag Bingo at Aquila’s Nest Vineyards(12 pm)
Norwalk: Fairfield County 9 Band at Calf Pasture Beach(5:00 pm - 7:00 pm)
Norwalk: Bim Skala Bim w/Demolition Brass Band at Pinkney Park(5:30PM)
Orange: GREEK FESTIVAL – St. Barbara (12pm-10pm)
Shelton: Griffin Anthony at Jones Winery(2–4pm)
Monday, Sept 1 – Labor Day Celebrations
Orange: GREEK FESTIVAL – St. Barbara (12pm-10pm)






