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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)

Newtown Holiday Festival Returns to Main Street on December 7

November 23, 2025
Join the Newtown Holiday Festival Dec 7 for family activities, 80+ vendors, performances, Santa visits, and festive fun benefiting NYFS.

FairfieldAfterDark’s Must-See Holiday Show Picks at The Palace Theatre Stamford

November 23, 2025
The holidays are almost here, and with Thanksgiving around the corner, our hearts are craving something deeper than the usual dinner-table chatter — real connection, real memories, and real magic. Every year we say, “Let’s do something different!” Well, THIS is the year to make it happen. With an incredible lineup of holiday shows lighting up The Palace Theatre in Stamford, your perfect opportunity to create unforgettable moments with family and friends has finally arrived. FairfieldAfterDark has handpicked the most exciting, heart-warming, and totally unforgettable performances of the season — something for every age, every vibe, and every holiday mood. Whether you're looking for nostalgic music, laugh-out-loud comedy, magical family fun, or iconic Christmas classics, these shows will leave a lasting impression for years to come. Holiday Happenings at The Palace Theatre Stamford — Our Must-See Lineup Nov 30 – Jessica Lynn’s A Very Merry Classic Christmas (7pm) A sparkling, feel-good holiday spectacular filled with soaring vocals, festive classics, and pure Christmas cheer. Dec 5 – Dave Attell (8pm) A night of razor-sharp, high-energy comedy from one of the most legendary stand-ups of our time. Dec 6 – Rock & Roll Playhouse: Music of Queen (12pm) A fun, interactive, family-friendly musical adventure introducing kids to the iconic songs of Queen. Dec 6 – Julia Cole (8pm) A powerful, crowd-pleasing country-pop performance packed with soulful vocals and infectious energy. Dec 7 – Mannheim Steamroller Christmas (7pm) A breathtaking holiday experience blending classical, modern, and magical sounds that define the season. Dec 19 – StevieMac: Fleetwood Mac Tribute Show (8pm) A stunning tribute capturing the timeless harmonies and emotional fire of Fleetwood Mac’s biggest hits. Dec 20 – Little River Band (6pm) An evening of smooth rock classics and iconic hits from one of the most enduring bands of the ’70s and ’80s. Dec 21 – Santa’s Circus (6pm) A whimsical holiday circus spectacular filled with acrobatics, laughter, color, and Christmas wonder for all ages. Dec 28 – The Canine Stars (3pm) A jaw-dropping stunt dog show featuring incredible pups performing unbelievable tricks and heartwarming moments. If you’re looking for the perfect way to celebrate the season, skip the stress and give yourself the gift of shared experiences. These shows promise joy, excitement, and memories that will warm your heart long after the lights go down. Let FairfieldAfterDark be your guide — and let The Palace Theatre Stamford be where your holiday magic begins.

Where to Host Your Next Big Event: Best Local Party Spots

November 23, 2025
Planning a party should feel exciting—not stressful. Whether you're gearing up for festive holiday gatherings, showers, weddings, milestone birthdays, or any celebration in between, choosing the right venue is the key to making your event unforgettable. Fairfield After Dark has explored some of the most unique, stylish, and memorable places in and around Fairfield County—from local vineyards like Aquila’s Nest, to trendy urban spots like 80 Proof American Kitchen, to comedy-club settings, historic landmarks, and even hosting your own red carpet event at The Palace Danbury. Whatever vibe you’re envisioning, we’ve rounded up the best of the best to help you find the perfect backdrop for your next celebration.

The Moonrise Cartel’s Star Continues to Rise

November 19, 2025
Black Rock, CT - The Moonrise Cartel is honored to announce that the band has been named Rising Star: Connecticut by the New England Music Awards — a distinction recognizing emerging artists whose work is shaping one of the most vibrant music scenes in the country. This recognition comes on the heels of a run of quickly-filled, often at-capacity shows across Fairfield County and beyond, reflecting the band’s growing presence and loyal following throughout the region. “We’re proud to represent such an incredible CT music community — and honored to be named Rising Stars of Connecticut by the New England Music Awards,” said Al Pascarelli, Founder, Lyricist and Vocalist for The Moonrise Cartel. “This community has supported us from the beginning, and we’re grateful to be growing together.” The New England Music Awards are presented annually to musicians whose dedication, spirit, and achievements have established them as a vital part of New England’s robust and diverse musical landscape. The NEMA nominating committee comprises journalists from major music publications, radio personalities, talent buyers, event planners, record-label executives and more — representing all six New England states and every awards category. Each year, the committee selects over 100 nominees across multiple genres, culminating in the coveted individual state awards that recognize a single artist or band as Best in State. NEMA also presents three Individual Awards each year to honor artists whose long-term contributions have meaningfully shaped New England’s music community.  You can catch The Moonrise Cartel opening for The Alternate Routes at FTC’s Warehouse on Saturday, December 6th, and headlining Upstage at The Stamford Palace on January 9, 2026.

Stamford Downtown Parade Spectacular Launches the 2025 Holiday Season November 23

By Cathy Ithier • November 19, 2025
Stamford Downtown Parade Spectacular Launches the Holiday Season November 23

John Denver Tribute: Rocky Mountain Christmas at Edmond Town Hall on December 5.

By Cathy Ithier • November 17, 2025
Thursday, December 5, 2025 | Doors 7:00 PM | Show 8:00 PM | Edmond Town Hall Celebrate the season with the timeless music of John Denver as Ted Vigil, the nation’s number one Denver tribute artist, brings his acclaimed show Rocky Mountain Christmas to Edmond Town Hal l on December 5 . Ted Vigil doesn’t just sound like John Denver — he embodies him. With an uncanny resemblance and heartfelt vocals, Vigil delivers an unforgettable performance that captures Denver’s warmth, sincerity, and spirit. Even Denver’s own lead guitarist, Steve Weisberg , has described Vigil’s act as “uncanny.” A Seattle native and lifelong musician, Vigil began performing at age ten and went on to win the Talent Quest 2006 competition as well as KOMO TV’s Celebrity Look-Alike Contest . He has since performed nationwide and appeared twice for John Denver’s Windstar Foundation in Aspen, Colorado. Enjoy favorite hits like “Take Me Home, Country Roads,” “Annie’s Song,” and “Thank God I’m a Country Boy,” along with holiday classics that will warm your heart. 🍷 Beer, wine, and concessions will be available for purchase throughout the evening. 🎟️ Don’t miss this magical holiday tribute! Visit EdmondTownHall.org to get your tickets before they sell out.
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