By Cathy Ithier
•
August 23, 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. 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 . 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.