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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!

Mar Jennings Takes the Stage with a Raw, One-Night-Only Performance

By Linda Kavanagh • April 16, 2026
America’s Top Lifestyle Expert Debuts Deeply Personal One-Man Show Benefiting Survivors of Domestic Violence Westport, CT: Mar Jennings, an Emmy®-nominated, nationally syndicated television host, award-winning Realtor, entrepreneur, philanthropist, and influencer, adds storyteller and performer to his dynamic career with “Mar Jennings — ONE-MAN SHOW”, a powerful and deeply personal production debuting May 22, 2026, at Sacred Heart University Community Theatre. This one-night-only performance is expected to sell out quickly. In a meaningful commitment to community impact, 100% of the proceeds will benefit The Center for Family Justice, supporting survivors of domestic violence, abuse, and trauma, with a fundraising goal of $200,000 going directly to the cause. “This chapter is about truth, legacy, and using my story for something bigger than myself,” says Jennings. “When I realized this show could raise real money for charity, it gave the project a deeper purpose. I’m ready to share my story now in a way I simply wasn’t before.” Years in the making, the production reflects both a lifetime of experiences and a turning point toward giving back in a more profound way. The result is a deeply human performance that balances vulnerability with purpose. Blending storytelling, humor, and raw honesty, Jennings shares a journey of resilience, reinvention, and hope, offering the audience an intimate, unfiltered look at overcoming life’s most difficult moments. “The hardest part is choosing what to reveal and what to hold sacred,” Jennings shares. “But if my story helps someone feel less alone, then every moment of discomfort is worth it.” Mar Jennings — ONE-MAN SHOW promises to be emotional, inspiring, and unforgettable, designed to create a genuine connection between performer and audience, reminding people that hope is real, that healing is possible, and that none of us are alone in the dark. "Mar’s decision to speak publicly about his journey marks an important moment, and we are grateful for his trust,” says Mark Antonini, President & CEO of The Center for Family Justice. “His voice will resonate with so many, and we are fully committed to supporting him and ensuring the success of this meaningful event.” “I’m ready to tell the whole story—the real one,” says Jennings. “If my journey can become a spark for someone else… if my pain can be transformed into power for others… then it all means something.” About Mar Jennings Mar Jennings is a nationally recognized lifestyle expert, bestselling author, television host, and speaker known for home design, entertaining, and lifestyle transformation. He is also a top-producing real estate professional and founder of The Mar Jennings Team, bringing his signature Casual Luxury® approach to every listing. Jennings uses his platform to inspire connection, positive change, and support for survivor advocacy. About The Center for Family Justice The Center for Family Justice provides crisis intervention, safe housing, counseling, and advocacy for survivors of domestic violence, sexual violence, and child abuse—helping individuals rebuild their lives with dignity and hope. Event Details Mar Jennings — ONE-MAN SHOW May 22, 2026 Sacred Heart University Community Theatre, Fairfield, CT Tickets: $54 http://shucommunitytheatre.showare.com/MarJenningsOne-ManShow

Aquila’s Nest Vineyards Invites Guests to a Sunset Sober Silent Disco in the Vines

By Neviana Zhgaba • April 15, 2026
A one-of-a-kind alcohol-free wellness dance experience showcasing elevated mocktails, mindful connection, and vineyard sunsets. NEWTOWN, CT — Aquila’s Nest Vineyards, Connecticut’s award-winning experience-focused vineyard and event venue, is redefining what a night out at the vineyard can look like with its upcoming “Sunset Session: Sober Silent Disco in the Vineyards.” This immersive golden-hour event invites guests to dance beneath the open sky with wireless headphones, curated music channels, breathtaking vineyard views, and a refreshing lineup of handcrafted mocktails and non-alcoholic beverages. Hosted in partnership with Autumn Fletcher, the event offers a vibrant alcohol-free social experience designed for guests seeking connection, movement, and joy in a mindful atmosphere. As the sun sets over the vines, attendees will sip beautifully crafted zero-proof drinks while enjoying the peaceful magic of the vineyard in a completely new way. “At Aquila’s Nest, we are proud to offer more than wine—we create experiences for every lifestyle and every guest ,” said Neviana Zhgaba, Co-Founder of Aquila’s Nest Vineyards. “From our signature mocktails to wellness gatherings, silent discos, yoga, and live music, we want everyone to feel they can fully enjoy the beauty of the vineyard in a way that feels right for them.” The Sunset Sober Silent Disco is part of Aquila’s Nest’s growing portfolio of inclusive experiences that showcase the vineyard as a destination for wellness, celebration, creativity, and community . Guests can expect an unforgettable evening where vineyard sunsets meet music, movement, and sophisticated zero-proof offerings that prove the vineyard experience extends far beyond the wine glass. The event will take place on Wednesday, May 27, 2026, from 7 PM to 8:45 PM , Early arrival is encouraged to enjoy mocktails before the sunset silent disco in the vines begins. For tickets and details, visit: Reserve Your Sunset Silent Disco Experience

Fairfield Hills Music Festival Returns May 16, 2026 in Newtown, CT Featuring 10 Bands, Food Trucks & Beer Garden — 6-Week Countdown Begins

By Cathy Ithier • April 14, 2026
Newtown, CT - Fairfield Hills Music Festival returns May 16 in Newtown, CT with 10 bands, two stages, food trucks, and a high-energy mix of national and local talent.

Step Into Style at Fashionably Westport 2026 — Hosted by the Westport Downtown Association

April 11, 2026
Westport, CT - The Westport Downtown Association, Inc. (WDA) presents Fashionably Westport for the sixth year, an evening that brings together fashion, community, and philanthropy in support of Homes with Hope. This year’s event promises an elevated yet intimate experience, featuring over twenty local boutiques, seven salons, and a dynamic lineup of 90 models. The Westport community is looking forward to coming together once again to celebrate this hometown event while supporting a meaningful cause. “The WDA is excited to host our 6th annual Fashionably Westport in support of Homes with Hope,” said Maxwell Crowley, President of the WDA. “It’s a great opportunity to bring the community together while highlighting and supporting our local businesses.” The event will be held at the Westport Library on Saturday, April 25th, from 7 to 10 p.m. Event Information: Visit the official event website Tickets: Purchase tickets on Eventbrite The WDA is honored to welcome Lonnie Quinn as co-emcee. Lonnie is an Emmy Award-winning meteorologist and has served as the Chief weathercaster for CBS News New York since 2007. A Westport resident, Quinn brings both energy and local connection to the evening. The WDA is excited to welcome back Dave Briggs as co-emcee. Briggs is a former CNN, NBC Sports, Fox News, and Turner Sports anchor. He has lived in Westport with his family since 2008. Finally, the WDA is excited to welcome the return of Carey Price , owner of Westport-based The Cove Collective, as runway director. Price is a Parsons School of Design alum with experience working alongside top fashion designers. No charity event is complete without a silent auction. The proceeds will benefit Homes with Hope. In 2024, the WDA raised $20,000, and hopes to exceed that goal this year. This year, the local business community has shown up in a big way, with over 100 donations. The silent auction is not to be missed. Explore all of the generous silent auction donors here , and stay tuned as the auction goes live on April 25, 2026, at 6:00 p.m.

Brews on Bedford in Stamford Downtown Returns on May 30!

By Stamford Downtown Special Services District • April 11, 2026
Stamford, CT — Brews on Bedford, presented by Stamford Downtown, returns on Saturday, May 30 from 2–5pm in Latham Park on Bedford Street, featuring craft beer. Tickets are on sale now through Afton . Guests can fill a sampling glass with beer from a variety of regional breweries while enjoying live music, lawn games, and local food vendors. Participating breweries include: Berlinetta Brewing, Best Friends Lunch, Captain Zig, Delta Seltzers, Greenwich Brewing Company, Half Full Brewery, Hop & Vine Tap Room, Nod Hill Brewery, Twelvenote Brew Co, Whalers and more to come! General Admission Tickets for Brews on Bedford are $30 for Early Birds until April 20, so get your tickets now! A limited number of VIP tickets are available for an additional $10, granting early entry at 1pm (VIP hours: 1–5pm). The entry fee includes a tasting glass, unlimited samples (while supplies last) and entertainment. All guests must be 21 or older. Valid ID is required for admission, including: A current motor vehicle operator’s license A state-issued identity card A valid passport or Global ID accompanied by another form of photo ID Digital IDs are not accepted. Please drink responsibly and know your limits. No pets or children under 21 will be admitted. Brews on Bedford is presented by Stamford Downtown and supported by Hey Stamford! and Star 99.9. For more information, visit Stamford Downtown Brews on Bedford and to purchase tickets, visit: BrewsonBedfordTicketsatAfton

An Icon. Legacy. A Night of Love: Smokey Robinson Live at The Palace Theatre Stamford on April 16.

By Cathy Ithier • April 7, 2026
Stamford, CT - Experience Smokey Robinson live at The Palace Theatre Stamford on April 16 during his Legacy of Love Tour. A night of timeless Motown hits awaits.
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