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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 π‘ to wildlife encounters π , live music πΆ, and food fests π΄, 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.
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
π‘
St. Leo’s Fair (Stamford, 6pm–10pm)
The rides, food, and family fun continue.
πΆ
ROYAL KINGS at Waveny Park Summer Concert (New Canaan, 7:30pm–9:30pm)
Free live music under the stars — bring a blanket and snacks.
πΌ
The Bernadettes – Music Under the Stars (Shelton, 7pm)
A family dance-along favorite!
π§©
Open Play Chess at Veterans Park(Stamford, 12pm–2pm)
A fun mix of strategy, fresh air, and community.
πΎ
Zoo & Treesure Hunt Combo (Bridgeport/Norwalk)
Perfect daytime adventures before the music begins.
- π£ 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)
- π£ Newtown: Meditation on Twin Hearts at Aquila's Nest Vineyards(7pm)
- π£ 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
π‘ St. Leo’s Fair (Stamford, 6pm–11pm)
A Labor Day week tradition for many families.
π
Beardsley Zoo + Skyhunters (Bridgeport, all day)
A great daytime activity before heading to evening fun.
πͺ Woodstock Fair – 164th Annual Kickoff (Woodstock, 4pm–9:30pm)
A classic agricultural fair with rides, food, and livestock — New England tradition at its best.
π¨ Summer Thursdays at Weston History & Culture Center (1pm–4pm)
Kid-friendly hands-on activities mixed with local history.
πΆ Outdoor Family-Friendly Music Across Fairfield County
Multiple towns host live music — an easygoing family night out.
- π£ Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)
- Bridgeport: Hurley Hour at Bryac Black Rock(6pm)
- Bridgeport: Chris Radz at The Castle(7pm-10pm)
- Danbury: Line Dancing at Elicit Danbury(7pm)
- π£ 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)
- π£ Newtown: Glen Roth LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm)
- π£ Newtown: Tarot Reading with Jenny Gypsy at Aquila's Nest Vineyards(5:30pm-9pm)
- π£ 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)
- π£ 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: Billy Genuario at Spotted Horse Tavern (9pm)
Friday, Aug 29 – Fairs & Outdoor Concerts
π‘ St. Leo’s Fair (Stamford, 6pm–9pm)
Friday night rides and lights!
πΎ Beardsley Zoo (Bridgeport, all day)
Always a top family adventure.
π Haddam Neck Fair (East Hampton, opens 3pm)
A long-running fair with rides, farm animals, and fireworks.
π Woodstock Fair (Woodstock, 12pm–9:30pm)
Day two of one of CT’s largest agricultural fairs.
πΆ 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)
- π£ 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)
- π£ Bridgeport: James Taylor & His All-Star Band at Hartford HealthCare Amp(7:30pm)
- 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)
- 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 at Milford Arts Council (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 - at the Sand Bar(8pm-11pm)
- Norwalk: Tom Petty Night at Washington Social(8pm-11:30pm)
- Norwalk: Tangled Vine at SOHO bar(9pm)
- Newtown: Johnny Chapman at Newsylum Brewing Co.(6pm-9pm)
- Newtown: Blimp Fest 2025: Case Galv & Code, Drink Baby, & Atlas AltaLIVE at Reverie Brewing(6:30pm-10pm)
- π£ Newtown: Bobby Wheeler LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm)
- π£ Newtown: Belgian Chocolate and Wine Pairing at Aquila's Nest Vineyards(6pm)
- π£ Newtown: Baked Brie & Vino Nights at Aquila's Nest Vineyards(6:30pm)
- π£ Newtown: Yappy Hour - Bring Your Furry Friends at Aquila's Nest Vineyards(6pm)
- π£ Newtown: The Lightfoot Band at Edmond Town Hall(8pm)
- Newtown: Orb Mellon at Perfusion(8pm-11pm)
- π£ Newtown: ETH DRIVE-IN: Dirty Dancing (PG-13)(9pm)
- Old Greenwich: Dad Bod Band at Bosco's Bar & Grill(9pm-11:30pm)
- Orange: GREEK FESTIVAL – St. Barbara (12pm-10pm)
- Redding: Jonny Chapman Trio at The Redding Roadhouse(7pm-10pm)
- Ridgefield: Phil & Isabel at Odeen’s Restaurant(5:30pm)
- Ridgefield: Corey Lewin at 850 Degree(6pm-9pm)
- Ridgefield: Nathaniel Hintz at Nod Hill Brewery(6:30pm)
- Rowayton: Not My Problem at Sails Bar & Grill(9:30pm-12am)
- Shelton: Riley Johnson at Jones Winery(5–7pm)
- π£ Stamford: That's Fair Comedy at New York Comedy Club Stamford(9:30pm)
- Stamford: Dive Bar Confessional at Half Full Brewery(7pm-9pm)
- π£ Stamford: Comedian Troy Bond at New York Comedy Club Stamford(7pm-9:30pm)
- Stratford: No Strings Attached at Windmill Tavern(5pm)
- Stratford: Frank Chiafari at Outriggers(5:30pm-8:30pm)
- Stratford: Stairway to Halen at Joey C’s Boathouse(9pm-12am)
- Woodbury: Macalas at Woodbury Brewing Company(8:30pm)
- π£ Westport: Picnic on the 4th of July at Music on Church Lane(6pm-9pm)
- Westport: Union Rail at Walrus Alley(7:30pm-11pm)
- Westport: Shell Shockt at Black Duck Cafe(9:30pm)
- π£West Redding: Book Fair - Mark Twain Library(9am-4pm)
Saturday, Aug 30 – Festivals & Fairs Galore
π΄
Fairfield International Food Fest at FTC (Fairfield, 4pm)
A global food adventure with live music and entertainment — perfect for families with adventurous eaters.
ππWest Redding: Book Fair - Mark Twain Library(9am-4pm) - Discover treasures for every reader at the annual Mark Twain Library Book Fair — thousands of books, family fun, and great summer reads!
π
Haddam Neck Fair (East Hampton, 3pm)
Tractor pulls, rides, and fireworks make this a highlight of the weekend.
π°
Connecticut Renaissance Faire – Opening Weekend (Lebanon, 10:30am–6pm)
Step back in time with jousting, costumed performers, and themed family fun.
π
Beardsley Zoo + Skyhunters (Bridgeport, 10am–2pm)
Perfect for a morning family outing before hitting the fairs.
- Bethel: MUDDY RIVER BLUES at Notch 8(8pm)
- Bridgeport: Acoustic Mafia at Boca Oyster Bar(5pm)
- Bridgeport: Ryan Collins at The Castle(8pm-11pm)
- Bridgeport: Sneaky Pete at Bryac Black Rock(9:30pm)
- Danbury: The Light w/Atom Rush at Sugar Hollow Taproom(8:30pm)
- Danbury: Get Lit at Elicit Brewing(9pm)
- Fairfield: El Camino at Sherman Green Gazebo(6:30-8:00 PM)
- π£π Fairfield: Fairfield International Food Fest at FTC(4pm)
- Fairfield: DJ DONNY D in the Speakeasy at Elicit Brewing(10pm)
- Fairfield: El Camino at Sherman Green Gazebo(6:30pm-8pm)
- Goshen: Goshen Fair(8am-9pm)
- Milford: STILETTO (BILLY JOEL TRIBUTE) at Stonebridge Restaurant(5pm)
- Milford: Bob Gotta at Cafe Atlantique(6:30pm-9:30pm)
- Middlefield: Corn Maze & Cider Donut Festival at Lyman Orchards(10am-4pm)
- New Milford: Street Survivors - Tribute to Lynyrd Skynyrd at Housatonic River Brewing(7pm-10pm)
- Norwalk: Norwalk’s Treesure Hunt(7am-7pm)
- Norwalk: What Up Funk Band at 314 Beer Garden(7:30pm-10:30pm)
- π£ Newtown: Mini Cheesecakes & Sweet Wines Pairing at Aquila's Nest Vineyards(12pm)
- π£ Newtown: Frandango at Aquila's Nest Vineyards(2:30pm-5:30pm)
- π£ Newtown: I Love the 80s to Death Murder Mystery at Aquila's Nest Vineyards(6pm)
- Newtown: Seth Adam at Newsylum Brewing Co(3pm-6pm)
- Newtown: Eric Christensen at Perfusion(8pm-11pm)
- π£ Newtown: ETH DRIVE-IN: Dirty Dancing (PG-13)(9pm)
- Orange: GREEK FESTIVAL – St. Barbara (12pm-10pm)
- Redding: Pimpinella at Milestone(9pm-12am)
- Ridgefield: Don Lowe at 850 Degree(6pm)
- Ridgefield: The Last Minutemen at Nod Hill Brewery(6:30pm)
- Stamford: Open Play Chess in Latham Park – Stamford(1pm-3pm)
- Stamford: Outsiders at Half Full Brewery(2pm-5pm)
- Stamford: St. Leo's Fair(2pm-11pm)
- Stamford: Cobblestone Road at The Beer Garden (Shippan Landing)(5pm-8pm)
- π£ Stamford: Comedians Meka Mo, Adam Muller, JC Mendoza, Brendan Sagalow at New York Comedy Club Stamford(4:30pm)
- π£ Stamford: Comedian Troy Bond at New York Comedy Club Stamford(7pm-9:30pm)
- Stamford: Superhero at Tigín Irish Pub(10pm)
- Stratford: Dawn & Greg at Outriggers(5:30pm-8:30pm)
- Stratford: Zac & Fried 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)
- π£ Westport: Vinnie Ferrone at Music on Church Lane(6pm-9pm)
- Westport: Massive Diva at Walrus Alley(7:30pm-11pm)
- Westport: Sucker Punch at Black Duck Cafe(9:30pm)
- Woodbury: Second Nature at Woodbury Brewing Company(8:30pm)
πβ¨ Bethel: Drag Brunch at Shakedown Street Eats (10am) – Brunch, glam, and fabulous performances!
π‘πΆ Goshen: Goshen Fair (8am–9pm) – Rides, food, live music & family fun all day.
π·πΎ Newtown: Wine & Wags at Aquila's Nest Vineyards (12pm) – Sip wine with your furry friends.
ποΈπΆ Norwalk: Bim Skala Bim w/Demolition Brass Band at Pinkney Park(5:30PM)– Outdoor ska & brass grooves by the water.
ππ West Redding: Book Fair – Mark Twain Library (10am–4pm) – Thousands of books & treasures for readers.
- Bethel: Bethel Holiday Weekend Craft Festival(11am-5pm)
- Bethel: BLACK ROCK 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: Chuck & Andy from the C-Sides LIVE at The Castle(5pm-8pm)
- East Hampton: Haddam Neck Fair(7:30am)
- Goshen: Goshen Fair(8am-9pm)
- Lebanon: 27th Annual Connecticut Renaissance Faire(10:30am-6pm)
- Milford: Rum Runners at Walnut Beach Pavillion(4-7pm)
- Milford: LABOR DAY SUNDAY W/ KATHY THOMPSON BAND LIVE at Stonebridge Restaurant(5pm)
- Middlefield: Corn Maze & Cider Donut Festival at Lyman Orchards(10am-4pm)
- New Milford: Parrothead Party Celebrating Jimmy Buffett with JAMIE'S JUNK SHOW at Housatonic River Brewing(4pm-7pm)
- Newtown: ZAC N' FRIED LIVE at Newsylum Brewing Co(12pm-5pm)
- π£Newtown: Wine & Wags at Aquila's Nest Vineyards(12pm)
- π£Newtown: Silent Disco White Party at Aquila's Nest Vineyards(6pm)
- π£Newtown: On the Road Again LIVE at Aquila's Nest Vineyards(2pm-5pm)
- π£ 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)
- Norwalk: Billy G and Friends at 314 Beer Garden(2:30pm-6pm)
- π£Orange: GREEK FESTIVAL – St. Barbara (12pm-10pm)
- π£Piermont, NY: Piano Brunch with Conal Fowkes at OTTO's(12pm-3pm)
- Ridgefield: Skylab at Nod Hill Brewery(2:30pm)
- Shelton: Griffin Anthony at Jones Winery(2–4pm)
- Shelton: Suck'R Punch at the Spotted Horse(4pm)
- Shelton: Da' Band at Pier 131 Kitchen(9:30pm)
- Stratford: Labor Day Weekend Hop Yard Clambake at Two Roads Brewing(12pm-4pm)
- Stratford: Mike LoQuidice at Outriggers(2pm-5pm)
- Stratford: What Up Funk at Joey C’s Boathouse(3pm-7pm)
- Stratford: Cooked Up at Windmill Tavern(8pm)
- π£Stamford: Comedians Matt Vita, Talal Alyan, Tyler Groce, Molly Brenner at New York Comedy Club Stamford(7pm)
- Westport: Savitsky Jazz Trio at Walrus Alley(5pm-7:30pm)
π‘πΆ Woodstock: 164th Annual Woodstock Fair (9am–7pm) – A true New England fair tradition.
π π¦ Bridgeport: Beardsley Zoo + Skyhunters in Flight (10am–2pm) – Animal adventures & bird show.
πΆπ· Newtown: Nayra & Cyril Acoustic Duo at Aquila’s Nest Vineyards (2:30pm–5:30pm) – Chill vineyard vibes.
ππ¬π· Orange: St. Barbara Greek Festival (12pm–6pm) – Food, music, culture & dancing.
πΆπ€ East Haven: Bluegrass Jam at the Museum (6pm–8:30pm) – Live Americana pickin’ to close out the holiday.
- East Hampton: Haddam Neck Fair(7:30am)
- Goshen: Goshen Fair(8am-6pm)
- Norwalk: Norwalk’s Treesure Hunt(7am-7pm)
- π£Newtown: Nayra & Cyril Acoustic Duo LIVE at Aquila's Nest Vineyards(2:30pm-5:30pm)
- π£Stamford:
Monday Night Mic at New York Comedy Club Stamford(7:30pm)
