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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)

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