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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 🎑 to wildlife encounters πŸ…, 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. 


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. 


Thursday, Aug 28 – Fairs, Culture & History 

🎑 St. Leo’s Fair (Stamford, 6pm–11pm) 
A Labor Day week tradition for many families. 

πŸ… Beardsley Zoo + Skyhunters (Bridgeport, all day) 
A great daytime activity before heading to evening fun. 

πŸŽͺ 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. 


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. 


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. 

πŸ“šπŸ“–West 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!

🎠 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. 

πŸ… Beardsley Zoo + Skyhunters (Bridgeport, 10am–2pm) 
Perfect for a morning family outing before hitting the fairs. 


Sunday, August 31

🎭✨ Bethel:  Drag Brunch at Shakedown Street Eats (10am) – Brunch, glam, and fabulous performances!

🎑🎢 Goshen:  Goshen Fair (8am–9pm)   – Rides, food, live music & family fun all day.

🍷🐾 Newtown:  Wine & Wags at Aquila's Nest Vineyards (12pm) – Sip wine with your furry friends.

πŸ–οΈπŸŽΆ Norwalk:  Bim Skala Bim w/Demolition Brass Band at Pinkney Park(5:30PM)– Outdoor ska & brass grooves by the water.

πŸ“šπŸ“– West Redding: Book Fair – Mark Twain Library (10am–4pm) – Thousands of books & treasures for readers.


ο»ΏMonday, Sept 1 – Labor Day 

🎑🎢 Woodstock:   164th Annual Woodstock Fair (9am–7pm) – A true New England fair tradition.

πŸ…πŸ¦… Bridgeport: Beardsley Zoo + Skyhunters in Flight (10am–2pm)   – Animal adventures & bird show.

🎢🍷 Newtown: Nayra & Cyril Acoustic Duo at Aquila’s Nest Vineyards (2:30pm–5:30pm)   – Chill vineyard vibes.

πŸ‡πŸ‡¬πŸ‡· Orange: St. Barbara Greek Festival (12pm–6pm)   – Food, music, culture & dancing.

🎢🎀 East Haven: Bluegrass Jam at the Museum (6pm–8:30pm) – Live Americana pickin’ to close out the holiday.

Labor Day Week-End Family Fun Guide: Top 5 Picks & more!

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By EJ Crawford • January 6, 2026
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Stamford Downtown Brings Back Fire & Ice Winter Festival on January 24th.

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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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