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Countdown to Labor Day: Family Fun & Local Adventures You’ll Love (Aug 24–30, 2025)
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.
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.
Sunday, Aug 24 – Fairs, Festivals & Outdoor Music
- 🦅Skyhunters in Flight at Connecticut’s Beardsley Zoo (Bridgeport, 11am–2pm)
Watch majestic birds of prey soar overhead in this thrilling live presentation — a must-see for families and animal lovers. - 🐯Beardsley Zoo Joins the CT Season Pass
(Bridgeport, all day)
Great news: Beardsley Zoo is now part of the statewide attraction pass, making it the perfect day trip with extra value. - 🎡Danbury San Gennaro Festival (Danbury, 1pm–10pm)
A family favorite with Italian food, carnival rides, live music, and cultural fun for all ages. - 🎭Chester Fair(Chester, 9am–6pm)
A slice of old-fashioned New England with livestock, games, rides, and local crafts. - 🎶Sound Beach Community Band – An Evening of Stephen Schwartz (Greenwich, 7pm)
Families can picnic at Binney Park while enjoying Broadway favorites under the stars.
- Bethel: DIRTY MARTINIS LIVE at Shakedown Street Eats(12pm)
- Bethel: $2 CAP Live at Notch 8(5pm)
- Bridgeport: The Rum Runners at Port 5 (3pm)
- Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)
- Bridgeport: Skyhunters in Flight at Connecticut's Beardsley Zoo(11am-2pm)
- Bridgeport: Ross & Bost LIVE atBoca Oyster Bar(5pm)
- Bridgeport: Fred & Ethel LIVE at The Castle(5pm-8pm)
- Brooklyn: CT Brooklyn Fair(9am-6pm)
- Danbury: Danbury San Gennaro Festival(1pm-10pm)
- Chester: Chester Fair(9am-6pm)
- Fairfield: Jazz Rabbi Greg Wall at Fairfield Museum (6:30 PM – 8:00 PM)
- Greenwich: Sound Beach Community Band-An Evening of Stephen Schwartz at Binney Park(7pm)
- Greenwich: Chris brown LIVE at Griff Club House(3pm-5pm)
- Greenwich: Kenny Weiss and Vicky Dussich LIVE at Bosco's Bar & Grill(4pm-7pm)
- Milford: Kathy Thompson Band at Walnut Beach Pavillion(4-9pm)
- Milford: BEATLES A TO Z (TRIBUTE TO THE BEATLES) LIVE at Stonebridge Restaurant(5pm)
- Middlefield: Lyman Orchards Sunflower Maze ~ Sesame Street(9am)
- Norwalk: Sensational Soul Cruisers at Calf Pasture Beach(5:00pm – 7:00pm)
- Norwalk: Norwalk’s Treesure Hunt(7am-7pm)
- Norwalk: Brunch with Fuzz LIVE at Washington Social(12pm-3pm)
- Newtown: Transformers One (PG) at Edmond Town Hall(1pm)
- Newtown: Pinot and Pilates at Aquila's Nest Vineyards(11am)
- Newtown: Sip & Shimmy Belly Dancing at Aquila's Nest Vineyards(12pm)
- Newtown: Bittersweet Descent LIVE at Aquila's Nest Vineyards(2pm-5pm)
- Newtown: Fine Cigars Night at Aquila's Nest Vineyards(6pm)
- Newtown: Reggae Meets Soul with Rho & The Nomads at Aquila’s Nest Vineyards(6pm-9pm)
- Newtown: Chris Cavaliere LIVE at Reverie Brewing(2p-5pm)
- Newtown: Dan's Garage Band LIVE at Newsylum Brewing Co(2pm-5pm)
- Piermont, NY: Sunday Piano Brunch with Kevin Lovejoy at OTTO's(12pm-3pm)
- Ridgefield: Abby Payne LIVE at Nod Hill Brewery(2:30pm)
- Ridgefield: Live Music with Gab Kallay at 850 Degree(5pm-8pm)
- Redding: On the Count of Two LIVE at Milestone(4pm-7pm)
- Stratford: Nashville Drive LIVE at Joey C’s Boathouse(3pm-7pm)
- Stratford: Alex Cano LIVE at Two Roads(2pm-4:30pm)
- Stratford: Brittany LIVE at Outriggers(2pm-5pm)
- Stamford: Sun Kings at Bartlett Arboretum & Gardens (5-7pm)
- Stamford: Comedy Jackpot Finals at New York Comedy Club Stamford(4pm)
- Shelton: Canyon at Jones Winery( 2–4pm)
- Shelton: Live Music from Tangled Vine! at Pier 131 Kitchen(5:30pm-8pm)
- Shelton: The Scratch Band LIVE at Spotted Horse(4pm)
- Valhalla, NY: Westchester Muslim Heritage Festival(12pm-6pm)
- Woodbury: Dan Ringrose LIVE at Woodbury Brewing Company(2pm)
- Westport: Elektrik Trio LIVE at Walrus Alley(5pm-8pm)
- Westport: Eight to the Bar LIVE at Levitt Pavilion(7pm)
Monday, Aug 25 – Family Adventures
- 🐾
Beardsley Zoo with CT Season Pass
(Bridgeport, all day)
A perfect family outing that now stretches your dollar even further. - 🌳
Norwalk’s Treesure Hunt (Norwalk, 7am–7pm)
An interactive scavenger hunt through town — kids love the adventure while parents enjoy the fresh air. - 🍦
Family Ice Cream Stops + Evening Strolls
Pair a zoo or hunt outing with your favorite local ice cream shop for a classic summer day. - 🗓️Plan Ahead for St. Leo’s Fair
(Stamford, opening Tuesday)
Get the kids excited for rides, food, and games later in the week. - ️🗓️ Plan Ahead for Woodstock Fair ( Opening Thursday)
Celebrate summer’s end at the 164th Annual Woodstock Fair, one of Connecticut’s longest-running traditions, with fun for all ages.
- Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)
- Norwalk: Norwalk’s Treesure Hunt(7am-7pm)
- Stamford: Monday Night Mic at New York Comedy Club Stamford(7:30pm)
Tuesday, Aug 26 – Fair Fun Begins
- 🎡St. Leo’s Fair
(Stamford, 6pm–10pm)
One of the area’s biggest family events with rides, carnival games, and treats — fun for all ages. - 🐅Beardsley Zoo
(Bridgeport, all day)
Always a family favorite, especially with the CT Pass perk. - 🌳Norwalk’s Treesure Hunt (Norwalk, all day)
Keep the kids busy exploring hidden gems throughout town. - 🎶Michelle Pauker LIVE at Villa Italia (Stamford, 6:30pm)
A great dinner outing with live entertainment. - 🎠
Classic Fair Food & Rides
Grab funnel cakes and cotton candy — the true taste of late summer.
- Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)
- Norwalk: Norwalk’s Treesure Hunt(7am-7pm)
- Stamford: St. Leo's Fair(6pm-10pm)
- Stamford: Michelle Pauker LIVE at Villa Italia Restaurant(6:30pm)
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)
- 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: Norwalk’s Treesure Hunt(7am-7pm)
- 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)
- 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: Chris Coogan at Jazz Fridays(6:30 PM – 8:00 PM)
- 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: 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)
- 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)
- 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: BADFOOT LIVE at Elicit Danbury(9pm)
- 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)
- 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: Live Music by Cobblestone Road at The Beer Garden (Shippan Landing)(5pm-8pm)
- 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)
👉 This guide keeps families busy all week long leading into Labor Day. Whether you love animals, live music, or classic fair traditions, there’s no shortage of fun.






