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Celebrate the Unofficial End of Summer with Labor Day Weekend Fun!
As summer winds down, the fun is just heating up! Fairfield After Dark has scoured the scene to bring you the best events happening this Labor Day Weekend. From outdoor concerts to vibrant festivals, there’s something for everyone. Plus, don't miss out on the chance to escape to the stunning Sullivan Catskills for a refreshing getaway! 🌄
Come Relax and Celebrate Labor Day in the Sullivan Catskills!
Book your Catskills Getaway here!
Tuesday, August 27
- 🎶 Norwalk: Open Jam in Freese Park | 7-10pm
- 🎺 Ridgefield: Tuba Skinny – Ballard Park – 485 Main St | 7-9pm
- 🍴 Stamford: Stamford Downtown Restaurant Week
- 🎡 Stamford: St. Leo’s Fair – 24 Roxbury Rd | 6-11pm
- 🎸 Stratford: Shot Down Band – Paradis Green - 121 Huntington Rd | 7pm
- 🎤 Trumbull: Mass Confusion – Trumbull Town Gazebo – 5866 Main St | 7pm
Wednesday, August 28
- 🎤 New Canaan: The Tom Duffy Band – Waveny Park – 677 South Ave | 7:30pm
- 🎸 Norwalk: One Hot Night with Tommy Lynn – Calf Pasture Beach | 7:30pm
- 🥁 Shelton: Silver Steel Band – Shelton Huntington Green – Huntington St | 7pm
- 🎡 Stamford: St. Leo’s Fair – 24 Roxbury Rd | 6-11pm
- 🎭 Stamford: Comedy Showcase with Gus Tate, Peter Wong, Maggie Lalley, Johnny MacDonald at NY Comedy Club Stamford – 230 Tresser Blvd | 7pm
Thursday, August 29
- 🍷 Newtown/Sandy Hook: Steve Capalbo – Aquila's Nest Vineyards – 56 Pole Bridge Rd | 5:30-8:30pm
- 🎷 Ridgefield: The Jim Kweskin Quartet with Samoa Wilson – Ballard Park – 485 Main St | 7-9pm
- 🎸 Stamford: The TNT Blues Revue – Street Beats in Columbus Park – Main St |6-8pm
- 🎡 Stamford: St. Leo’s Fair – 24 Roxbury Rd | 6-11pm
- 🎭 Stamford: Clean Comedy with Collin Chamberlin & Steven Rogers at New York Comedy Club Stamford-230 Tresser Blvd | 7pm
Friday, August 30
- 🎤 Bridgeport: Young Miko – XOXO Tour – Hartford HealthCare Amp – 500 Broad St | 8pm
- 🎶 Bethlehem: Long River Jams – March Farm – 160 Munger Ln | 6:30pm
- 🎸 Danbury: Apolo’s Band – Danbury City Center Green – 1 Ives St | 7-9 pm
- 🥁 Fairfield: Jim Royle’s Caribbean Connection – Fairfield Museum & History Cnt – 370 Beach Rd | 6:30pm
- 🎸 Fairfield: Fairfield County Jam – The Warehouse of FTC – 70 Sanford St | 7pm
- 🎤 Fairfield: Ruthie Foster – StageOne at FTC – 70 Sandford St | 7:45pm
RESCHEDULED TO WED OCT 2 @ 7:45PM
- 🎡 Haddam: Haddam Neck Fair – 26 Quarry Hill Rd, East Hampton CT | 4pm
- 🍷 Newtown/Sandy Hook: Alison Turner – Aquila's Nest Vineyards –56 Pole Bridge Rd | 5:30-8:30pm
- 🎡 Orange: St. Barabara Greek Festival – 480 Racebrook Rd | 12noon-10pm
- 🎤 Shelton: Holley McCreary – Jones Family Farms – 606 Walnut Tree Hill Rd | 5-7pm
- 🎡 Stamford: St. Leo’s Fair – 24 Roxbury Rd | 6-11pm
- 🎭 Stamford: Showcase Show with Ja-Ron Young, Katie Boyle, Julio Diaz, Nick Simmons at New York Comedy Club Stamford-230 Tresser Blvd | 7pm
- 🎭 Stamford: That's Fair Comedy ft: Chris Cyr, Chanel Ali, Josh Mandl, Cody Marino at NY Comedy Club Stamford 230 Tresser Blvd | 9:30pm
- 🎸 Weston: Logical Pretzel – Lachat Town Farm – 106 Godfrey Rd W | 6pm
- 🎶 Westport: John Richers – Music on Church Lane | 6-9 pm
- 🎡 Woodstock: 163rd Woodstock Fair – 281 CT-169 | 12pn-11pm
Saturday, August 31
- 🎷 Bridgeport: Jazz Festival at Downtown McLevy Green - 102 Bank St | 12pm-8pm
- 🎤 Bridgeport: Walker Hayes – Hartford HealthCare Ampitheater – 500 Broad St | 7pm
- 🎸 Bridgeport: ACE & Friends – BRYAC BlackRock 3074 Fairfield Ave | 9pm
- 🌽 Brookfield: The Corn Maze at Twins BBQ – 401 Federal Rd | 10:30am-5:30pm
- 🎸 Danbury: The Midnight Rock Show – The Palace Danbury – 165 Main St | 8pm
- 🎤 Fairfield: Sister Sparrow & The Dirty Birds – Fairfield Theatre Company in The Lot – 70 Sandford St | 8pm
- 🎡 Goshen: Goshen Fair – 116 Old Middle St , Goshen, CT | 8am-9pm
- 🎡 Haddam: Haddam Neck Fair – 26 Quarry Hill Rd, East Hampton CT | 4pm
- 🏰 Lebanon: The Connecticut Renaissance Faire – 122 Mack Rd | 10:30am-6pm
- 🍎 Middlefield: Corn Maze & Cider Donut Festival – Lyman Orchards – 32 Reeds Gap Rd | 10am-4pm
- 🍷 Newtown/Sandy Hook: Long River Jam – Aquila's Nest Vineyards – 56 Pole Bridge Rd | 2:30-5:30pm
- 🎡 Orange: St. Barabara Greek Festival – 480 Racebrook Rd | 12noon-10pm
- 🎡 Stamford: St. Leo’s Fair – 24 Roxbury Rd | 2-11pm
- 🎭 Stamford: Showcase Comedy with Mia Jackson, Christian Finnegan, Marion Grodin, Mike Finoia at NY Comedy Club Stamford 230 Tresser Blvd | 2 Shows | 7 & 9:30pm
- 🎶 Westport: Steve Ferentzy – Music on Church Lane | 6-9pm
- 🎡 Woodstock: 163rd Woodstock Fair – 281 CT-169 | 9am-11pm
Sunday, September 1
- 🌽 Brookfield: The Corn Maze at Twins BBQ – 401 Federal Rd | 10:30am-5:30pm
- 🚗 Danbury: Danbury Car & Truck Festival – 1 Memorial Dr | 10am-4pm
- 🎸 Fairfield: Herman & Company – Sherman Town Green- 1451 Post Rd | 4:30pm
- 🎡 Goshen: Goshen Fair – 116 Old Middle St , Goshen, CT | 8am-9pm
- 🕯️ Groton: Candlelight Remebrance Ceremony at Fort Griswold – Park Ave & Monument St | 6pm
- 🎡 Haddam: Haddam Neck Fair – 26 Quarry Hill Rd, East Hampton CT | 4pm
- 🏰 Lebanon: The Connecticut Renaissance Faire – 122 Mack Rd | 10:30am-6pm
- 🍎 Middlefield: Corn Maze & Cider Donut Festival – Lyman Orchards – 32 Reeds Gap Rd | 10am-4pm
- 🎸 Milford: Rum Runners – Devon Rotary Pavilion – 113 E. Broadway | 4-7pm
- 🎸 Newtown/Sandy Hook: North County Trio – Aquila's Nest Vineyards – 56 Pole Bridge Rd | 2:30-5:30pm
- 🎸 Norwalk: Junco Partners – Barley Beach – 11 Pine Point Rd | 4:30pm
- 🎡 Orange: St. Barabara Greek Festival – 480 Racebrook Rd | 12noon-10pm
- 🎸 Shelton: Seth Adam – Jones Family Farms – 606 Walnut Tree Hill Rd | 2-4pm
- 🎡 Windsor: CT River & Roots Festival – 275 Broad St | 12pm-6pm
- 🎡 Woodstock: 163rd Woodstock Fair – 281 CT-169 | 9am-11pm
Monday, September 2
- 🎡 Haddam: Haddam Neck Fair – 26 Quarry Hill Rd, East Hampton CT | 4pm
- 🎡 Goshen: Goshen Fair – 116 Old Middle St , Goshen, CT | 8am-6pm
- 🏰 Lebanon: The Connecticut Renaissance Faire – 122 Mack Rd | 10:30am-6pm
- 🎈🎷 Newtown: LaborDay Parade – Main Street | 9:55am
- 🍷 Newtown/Sandy Hook: Shawn Taylor – Aquila's Nest Vineyards – 56 Pole Bridge Rd | 1-4pm
- 🎡 Orange: St. Barabara Greek Festival – 480 Racebrook Rd | 12noon-6pm
- 🎡 Woodstock: 163rd Woodstock Fair – 281 CT-169 | 9am-8pm
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.
Norwalk, CT - Experience Odeen’s in Norwalk this week for speed dating, trivia night, and live music with Exit 5. Great food, fun vibes, and new connections await!
First-of-Its-Kind Event Brings Together Talented Young Artists from Across the Region. Danbury, CT – Get ready, art lovers! CityCenter Danbury is thrilled to announce the Danbury Rising Art Expo, a vibrant celebration of creativity featuring emerging artists from our local community. This dynamic exhibition is your chance to experience the bold, fresh perspectives of the next generation of local talent, all in the heart of Downtown Danbury! Sunday, April 12, 2026 12:00 PM – 4:00 PM Arthur Murray Dance Studio , 345 Main Street, Danbury, CT 06810 FREE ADMISSION – Open to the Public Visitors will be immersed in an exciting pop-up gallery featuring a wide variety of artwork, from stunning visual pieces to interactive installations. Guests can meet the artists, participate in live Q&A sessions, and even catch live open-mic interviews, making this more than just an exhibition, it’s a full celebration of creativity, community, and culture! Light bites and refreshments will be provided, generously sponsored by Mothership Bakery , ensuring your experience is both visually and gastronomically delightful. “We are beyond excited to shine a spotlight on the rising talent in our community,” said Lazaro Chavez, Executive Director of CityCenter Danbury. “The Danbury Rising Art Expo is more than just an art show, it’s a showcase of imagination, innovation, and the incredible creativity thriving right here in Downtown Danbury.” Don’t miss this one-of-a-kind pop-up art experience! Come support local artists, connect with your community, and discover the future of art in Danbury. For more information, visit www.citycenterdanbury.com About CityCenter Danbury CityCenter Danbury is a nonprofit organization dedicated to fostering arts, culture, and economic vitality in downtown Danbury. Through engaging events and community initiatives, CityCenter Danbury continues to enhance the city’s cultural landscape and bring people together.
Sandy Hook, CT - 35,000 daffodils bloom at Aquila’s Nest Vineyards in Sandy Hook, with golden sunsets creating one of Connecticut’s most stunning spring views.
Bridgeport, CT - Tickets on sale for Beardsley Zoo’s 20th Wild Wine Safari—June 6. Enjoy 50+ tastings, live music, auctions & animal encounters at this unique 21+ event.
Brookfield Film Festival returns March 27–29 with indie films, shorts, live script readings & filmmaker Q&As at Brookfield Theatre for the Arts.