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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.  


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 


  1. 🦅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. 
  2. 🐯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. 
  3. 🎡Danbury San Gennaro Festival (Danbury, 1pm–10pm) 
    A family favorite with Italian food, carnival rides, live music, and cultural fun for all ages. 
  4. 🎭Chester Fair(Chester, 9am–6pm) 
    A slice of old-fashioned New England with livestock, games, rides, and local crafts. 
  5. 🎶Sound Beach Community Band – An Evening of Stephen Schwartz (Greenwich, 7pm) 
    Families can picnic at Binney Park while enjoying Broadway favorites under the stars. 

 

Monday, Aug 25 – Family Adventures 


  1. 🐾 Beardsley Zoo with CT Season Pass (Bridgeport, all day) 
    A perfect family outing that now stretches your dollar even further. 
  2. 🌳 Norwalk’s Treesure Hunt (Norwalk, 7am–7pm) 
    An interactive scavenger hunt through town — kids love the adventure while parents enjoy the fresh air. 
  3. 🍦 Family Ice Cream Stops + Evening Strolls 
    Pair a zoo or hunt outing with your favorite local ice cream shop for a classic summer day. 
  4. 🗓️Plan Ahead for St. Leo’s Fair (Stamford, opening Tuesday) 
    Get the kids excited for rides, food, and games later in the week. 
  5. ️🗓️ 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. 


Tuesday, Aug 26 – Fair Fun Begins 


  1. 🎡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. 
  2. 🐅Beardsley Zoo (Bridgeport, all day) 
    Always a family favorite, especially with the CT Pass perk. 
  3. 🌳Norwalk’s Treesure Hunt (Norwalk, all day) 
    Keep the kids busy exploring hidden gems throughout town. 
  4. 🎶Michelle Pauker LIVE at Villa Italia (Stamford, 6:30pm) 
    A great dinner outing with live entertainment. 
  5. 🎠 Classic Fair Food & Rides 
    Grab funnel cakes and cotton candy — the true taste of late summer. 


Wednesday, Aug 27 – Outdoor Music & Family Nights

 

  1. 🎡 St. Leo’s Fair (Stamford, 6pm–10pm) 
    The rides, food, and family fun continue.
  2. 🎶 ROYAL KINGS at Waveny Park Summer Concert (New Canaan, 7:30pm–9:30pm) 
    Free live music under the stars — bring a blanket and snacks.
  3. 🎼 The Bernadettes – Music Under the Stars (Shelton, 7pm) 
    A family dance-along favorite!
  4. 🧩 Open Play Chess at Veterans Park (Stamford, 12pm–2pm) 
    A fun mix of strategy, fresh air, and community.
  5. 🐾 Zoo & Treesure Hunt Combo (Bridgeport/Norwalk) 
    Perfect daytime adventures before the music begins. 


Thursday, Aug 28 – Fairs, Culture & History 


  1. 🎡 St. Leo’s Fair (Stamford, 6pm–11pm) 
    A Labor Day week tradition for many families. 
  2. 🐅 Beardsley Zoo + Skyhunters (Bridgeport, all day) 
    A great daytime activity before heading to evening fun. 
  3. 🎪 Woodstock Fair – 164th Annual Kickoff (Woodstock, 4pm–9:30pm) 
    A classic agricultural fair with rides, food, and livestock — New England tradition at its best. 
  4. 🎨 Summer Thursdays at Weston History & Culture Center (1pm–4pm) 
    Kid-friendly hands-on activities mixed with local history. 
  5. 🎶 Outdoor Family-Friendly Music Across Fairfield County 
    Multiple towns host live music — an easygoing family night out. 


Friday, Aug 29 – Fairs & Outdoor Concerts

 


Saturday, Aug 30 – Festivals & Fairs Galore 


  1. 🍴 Fairfield International Food Fest at FTC (Fairfield, 4pm) 
    A global food adventure with live music and entertainment — perfect for families with adventurous eaters. 
  2. 🎠 Haddam Neck Fair (East Hampton, 3pm) 
    Tractor pulls, rides, and fireworks make this a highlight of the weekend. 
  3. 🏰 Connecticut Renaissance Faire – Opening Weekend (Lebanon, 10:30am–6pm) 
    Step back in time with jousting, costumed performers, and themed family fun. 
  4. 🎡 St. Leo’s Fair (Stamford, 2pm–11pm) 
    A full day of rides, games, and food — kids’ favorite stop of the week. 
  5. 🐅 Beardsley Zoo + Skyhunters (Bridgeport, 10am–2pm) 
    Perfect for a morning family outing before hitting the fairs. 

 


👉 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. 



Countdown to Labor Day: Family Fun & Local Adventures You’ll Love (Aug 24–30, 2025)

Gabby’s Dollhouse LIVE! Comes to The Palace Theatre Stamford on January 24

January 6, 2026
Gabby’s Dollhouse LIVE! comes to The Palace Theatre Stamford on January 24. Enjoy a magical, music-filled family show with Gabby and friends.

Verso Studios at The Westport Library Presents First-Ever Battle of the Bands

By EJ Crawford • January 6, 2026
Westport, CT - Verso Studios, the media arm of The Westport Library, is excited to announce its first-ever Battle of the Bands , an electrifying live music event celebrating the next generation of Fairfield County talent. Taking place Saturday, January 10, in the Library’s incomparable Trefz Forum, the high-energy showcase will feature four standout teen and college-aged bands: The Breakers, Clockwork, Caravan, and MOSS . Doors open at 7 pm , with the show beginning at 8 pm . Tickets are $10 for students and $20 for general admission, and can be purchased here . More than just a concert, this interactive competition puts the outcome entirely in the hands of the audience. Attendees will vote at the end of the night to determine the winner, awarding a $500 grand prize to first place and $250 to second place. Verso Studios is dedicated to amplifying creativity, collaboration, and community, and the debut of this Battle of the Bands marks an exciting new initiative in support of local live music. The event brings together emerging artists and music fans for a night that celebrates original sound, high-energy performance, and grassroots support for the local music scene. Whether attendees come to support a favorite band or discover something new, the event promises an unforgettable experience where community engagement plays a central role. Event Details Location: Trefz Forum, The Westport Library, 20 Jesup Road, Westport, CT 06880 Doors: 7 pm Show: 8 pm Bands: The Breakers, Clockwork, Caravan, MOSS Audience-voted competition with cash prizes Tickets and additional information: https://westportlibrary.org/event/verso-studios-presents-battle-of-the-bands/

Brookfield Film Festival Submissions Deadline February 26th.

By Brookfield Arts Commission • January 6, 2026
Brookfield Film Festival: A Small Town with a Big Film Legacy Brookfield, CT - Brookfield, Connecticut may be a small town, but it holds a meaningful place in the regional film community. Located in Fairfield County within the southern foothills of the Berkshire Mountains, Brookfield is bordered by Candlewood Lake and Lake Lillinonah and sits just 43 miles northeast of New York City. With a population of approximately 17,000, the town has become a welcoming hub for independent filmmakers. Now in its 18th year, the Brookfield Film Festival continues to gain momentum inside the historic Brookfield Theatre for the Arts. Sponsored by the all-volunteer Brookfield Arts Commission, the festival not only celebrates independent film, but also supports arts education. Proceeds benefit the Brookfield Arts Commission Arts Scholarship Award, presented annually to a graduating Brookfield high school senior pursuing a degree in the arts. This year’s two-day festival features four curated program blocks. Regional Indie Afternoon showcases films from Connecticut and neighboring states, followed by filmmaker Q&A discussions. Read-Through Indie Morning, presented with the Brookfield Theatre for the Arts, gives screenwriters the opportunity to hear their work read aloud and network with actors and filmmakers in a collaborative setting, complete with complimentary coffee and pastries. Shorts and to the Point highlights a handpicked selection of Oscar-nominated and award-winning short films, while Music Indie Evening features original music videos from regional artists and filmmakers. The Brookfield Film Festival takes place March 27 through March 29 at the Brookfield Theatre for the Arts, located at 184 Whisconier Road in Brookfield, CT. A $15 suggested donation supports festival programming and scholarships. Light refreshments and festival merchandise will be available throughout the weekend. With its intimate atmosphere, diverse programming, and strong community focus, the Brookfield Film Festival proves that big creative impact can come from a small town.

Stamford Downtown Brings Back Fire & Ice Winter Festival on January 24th.

By Stamford Downtown Special Services District • January 6, 2026
Stamford, Ct - Stamford Downtown is excited to announce the return of the beloved Fire & Ice Winter Festival , bringing warmth, artistry, and winter fun back to Columbus Park on Saturday, January 24, 2026, from 1:00 to 5:00 PM . A favorite seasonal tradition, Fire & Ice offers a dynamic afternoon for all ages. Visitors can gather around cozy fire pits, watch live ice sculpting demonstrations by talented professional artists, and enjoy live music throughout the park. Nearby Columbus Park restaurants will add to the experience with inviting indoor and outdoor dining options, creating a lively and welcoming winter atmosphere. This FREE community festival celebrates the best of winter in Stamford Downtown—bundled-up fun, glowing fires, sparkling ice, and shared moments. Don’t miss this signature winter event!

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