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Fairfield County Weekend Guide: Holiday Craft Fairs, Concerts, Comedy Shows & Fall Festivals Near You.
🎃 Now that Halloween is officially in the rearview mirror, it’s time to trade spooky thrills for cozy chills and kick off a new season of Fall Fun Adventures in and around Fairfield County! From festive pop-up Holiday Craft Fairs and charming local artisan markets to nights filled with live music, touring national acts, belly-laughing comedy shows, and colorful fall festivals, there’s so much to explore. Whether you’re in the mood for a laid-back vineyard concert, a family-friendly fair, or an after-dark comedy lineup with friends, we’ve got your week covered. Our daily listings are organized for Fall Fun Adventures all day and night — just pick your day, pick your town, and click on it! Boom — Instant Adventure, Fairfield After Dark Fans! Let’s make November unforgettable — one cozy, music-filled, laughter-packed day at a time.
- Bethel: Sarah Cion & Steps Behind Feat. Bill Reeve, Mike Rubino & Dave Livolsi LIVE at La Zingara(7pm-9:15pm)
- Fairfield: End of The Line A Tribute to the Allman Brothers Band on StageOne in FTC!(8pm)
- 🌟 Newtown: Dumpling Making Class at Aquila's Nest Vineyards(6pm)
- 🌟 Newtown: Salsa & Bachata Dance Night at Aquila's Nest Vineyards(6pm)
- 🌟 Stamford: Sessions & Confessions with Kevin Herrera at New York Comedy Club Stamford(7pm)
- Bridgeport: Ladies Game Day at Port 5 Naval Vets(1pm-3pm)
- Danbury: Line Dancing at Elicit Brewing - Danbury(7pm)
- Danbury: Thursday Open Jam w/ Fuzz LIVE at Sugar Hollow Taproom(8pm-10pm)
- Fairfield: ETA Music LIVE at The Sinclair(8:30pm)
- 🌟 Newtown: Wine, Words & Wisdom Book Club Series at Aquila's Nest Vineyards(6:30pm)
- 🌟 Newtown: WISHBONE ASH at Edmond Town Hall(7:30pm-10pm)
- Norwalk: Live music with STEVEN KEITH!(5:30pm-8:30pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Old Greenwich: Mojo LIVE at Bosco's Bar & Grill(9pm-12am)
- Redding: Midnight Cardinal LIVE at Milestone(7:30pm)
- Ridgefield: Traditional Irish Session LIVE at Nod Hill Brewery(6pm)
- Rowayton: DEVIN DAVERSA LIVE at Sails American Grill(6pm-9pm)
- 😂 Stamford: Comedian Jeff Arcuri at New York Comedy Club Stamford(7pm)
- Westport: Steve Johns Mythology CT CD LIVE at Jazz Society Of Fairfield County(7:30pm-10pm)
- Bethel: DAN LYON LIVE at Shakedown Street Eats(6:30pm)
- Bethel: JAKE KULAK BAND LIVE at Notch8 Bar(8pm)
- Danbury: Sex & Candy LIVE at Elicit Brewing - Danbury(7pm-9pm)
- Danbury: Zach Anderson LIVE at Charter Oak Brewing(7pm-9pm)
- Danbury: Live Irish music: John Whelan & Dylan Foley in concert 11/7/25(7pm-10pm)
- Danbury: Gratefully Yours LIVE at Sugar Hollow Taproom(8:30pm)
- Danbury: DJ ILARDI LIVE at Elicit Brewing - Danbury(10pm)
- 🎁 Montville: New England Christmas Festival(9am)
- Milford: IAN BIGGS LIVE at StoneBridge Restaurant(7pm)
- New Milford: The Remnants LIVE at Housatonic River Brewing(7pm-10pm)
- 🌟 Newtown: The 80s Rock Experience Tribute Show at Aquila's Nest Vineyards(6pm)
- Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm)
- Newtown: DJ Sienna LIVE at The Perfusion Bar(8pm)
- Newtown: Comeback Kings Live at Reverie Brewing(6pm-9pm)
- 🌟Norwalk: BENNY MIKULA LIVE at SONO 1420(6pm-9pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Norwalk: Scratch Live at 314 Beer Garden(7pm-11pm)
- Old Greenwich: Captain Obvious LIVE at Bosco's Bar & Grill(9pm-12am)
- Redding: Max Wareham & the National Bluegrass Team LIVE at The Granite Church(7pm)
- Redding: Mike Milazzo LIVE at The Redding House(7pm-10pm)
- Ridgefield: Reed Foehl LIVE at Nod Hill Brewery(7pm)
- Rowayton: Tangled Vine LIVE at Sails American Grill(9:30pm)
- Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm)
- Shelton: Happy Sally LIVE at Pier 131(9:30pm-12am)
- 🌟 Stamford: Comedian Jeff Arcuri at New York Comedy Club Stamford(7pm-9:30pm)
- 🌟 Stamford: A Live Conversation with Rainn Wilson at The Palace Theatre Stamford(8pm)
- Stamford: T.A.N. BAND LIVE at Third Place by Half Full Brewery(8pm-10pm)
- Stamford: Just Below Me LIVE at Tiernan's Bar & Restaurant(9:30pm)
- Stratford: Murray the Wheel LIVE at Windmill Tavern(5pm)
- Stratford: Saltwater RIOT LIVE at Windmill Tavern(8pm)
- Stratford: The Greg Sherrod Band LIVE at Joey C's BoatHouse(9pm-12am)
- Weston: Weston Library Book Sale(9am)
- Westport: Bad Manners LIVE at Black Duck Cafe(9:30pm)
- Bridgeport: 18th Annual AmFab Open Studios(10am-5pm)
- Bethel: ROVING SON LIVE at Shakedown Street Eats(6:30pm)
- Bethel: BLUESEYLAND LIVE at Notch8 Bar(8pm)
- 🎁 Danbury: A Very Gifty Christmas - Danbury(10am-4pm)
- Danbury: Diwali Celebration at the Danbury Library(11am)
- Danbury: Music Festival For a Cause LIVE at Charter Oak Brewing(1pm-9pm)
- 🌟 Danbury: Yellow Brick Road - A Tribute to Elton John at The Palace Danbury Theatre(7:30pm)
- Danbury: Vinyl Cut LIVE at Sugar Hollow Taproom(8:30pm)
- Danbury: Heavy Hitters LIVE at Elicit Brewing - Danbury(9pm)
- Danbury: DJ Pickz LIVE at Elicit Brewing - Danbury(10pm)
- Danbury: THE ZOO LIVE at Molly Darcy's Irish Pub & Restaurant(10pm)
- Derby: AG3 LIVE at Badsons Beer Co.(6pm)
- 🎁 Montville: New England Christmas Festival(9am)
- 🎁 Meriden: Weihnachtsfest Christmas Bazaar - Meriden(9am-3pm)
- Milford: Milford CT - North County Band w/s/g Drew Ryder Smith(7:30pm)
- 🎁 Milford: Kicking Off The Holidays - Pop Shop Market Milford(10am-4pm)
- New Canaan: Fan Fiction LIVE at Gates Restaurant & Bar(8:30pm-11:30pm)
- New Milford: Southern Desperation LIVE at Housatonic River Brewing(7pm-10pm)
- 🌟 Newtown: Fall Fair at Christ the King Church (9am-3pm)
- 🌟 Newtown: Fall Desserts & Wine Pairing at Aquila's Nest Vineyards(12pm)
- 🌟 Newtown: Dueling Pianos with the Flying Ivories at Aquila's Nest Vineyards(6pm)
- 🌟 Newtown: Acoustic Mafia LIVE at Aquila's Nest Vineyards(2pm-5pm)
- Newtown: Mike & Ike LIVE at Newsylum Brewing Co.(3pm-6pm)
- Newtown: Ralph Judson LIVE at The Perfusion Bar(8pm-11pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Norwalk: Tangled Vine LIVE at 314 Beer Garden(7:30pm-11pm)
- Redding: Fake ID LIVE at Milestone(8:30pm-12am)
- Ridgefield: Chris Berry & Abe Seiferth LIVE at Nod Hill Brewery(6:30pm)
- Sherman: Wonsey Jazz Trio LIVE at JCC In Sherman(7pm-9pm)
- Shelton: LOUBIRDMUSIC LIVE at Pier 131(9:30pm)
- 🌟 Stamford: Comedians Dan St. Germain, Meka Mo, Max Antonucci, Neko White at New York Comedy Club Stamford(4:30pm)
- 🌟 Stamford: Comedian Jeff Arcuri at New York Comedy Club Stamford(7pm-9:30pm)
- 🌟 Stamford: NEEDTOBREATHE at The Palace Stamford(7:30pm)
- Stamford: Ulysses and the Leftys LIVE at Tiernan's Bar & Restaurant(9:30pm)
- Stratford: Sister Funk LIVE at Windmill Tavern(8pm)
- Stratford: Not My Problem LIVE at Joey C's BoatHouse(9pm-12am)
- Weston: Weston Library Book Sale(9am)
- Westport: N.O.S. Band LIVE at Black Duck Cafe(9:30pm)
- Bethel: RICH MOLDEN LIVE at Shakedown Streets Eats(12pm)
- Danbury: Tangled Vine LIVE at Sugar Hollow Taproom(4pm)
- 🎁 Hamden: Howliday Hoopla at Quinnipiac University(10am-4pm)
- 🎁 Montville: New England Christmas Festival(9am)
- 🎁 North Haven: North Haven Holiday Welcome Craft Festival(11am)
- New Milford: Seth Adam LIVE at Housatonic River Brewing(4pm-7pm)
- 🌟 Newtown: The Music of Sabrina Carpenter at Aquila's Nest Vineyards(12pm)
- 🌟 Newtown: The Mighty Soul Drivers - Memphis in CT at Aquila's Nest Vineyards(4pm-8pm)
- Newtown: Willie Portera Trio LIVE at Newsylum Brewing Co.(2pm-5pm)
- 🌟 Newtown: Beginnings (Chicago Tribute) AT Edmond Town Hall(7pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Newtown: Otis & the Hurricanes Trio Live at Reverie Brewing(2pm-5pm)
- Sherman: "Leaving Kiev: Coming Full Circle" One Woman Show with Mila Levine LIVE at JCC In Sherman(3pm-5pm)
- 🌟 Stamford: Rock and Roll Playhouse Plays: Music of The Grateful Dead & More For Kids at The Palace Theatre Stamford(12pm)
- 🌟 Stamford: Comedians Dan Altano, Pranav Behari, Tom Cassidy, Nonye Brown-West at New York Comedy Club Stamford(7pm)
- 🎁 Torrington: 3rd Annual Torrington Christmas Holiday Festival(10am-3pm)
- Weston: Weston Library Book Sale(9am)
Celebrate 3 years of laughs on March 1 at 4:30 PM with a special matinee showcase featuring top comics, great vibes, and nonstop stand-up fun.
Connecticut folk-rock favorites The Moonrise Cartel bring soaring harmonies and high-energy Americana to Daryl’s House in Pawling, NY on April 9. Get tickets now.
Enjoy a free “Blues & Beyond” concert at First Congregational Church of Stamford in Stamford, exploring African American history through music. Reserve seats now.
Join Team Woofgang & Co. for Bunco Blast on Feb 26—games, drinks, and fun supporting adults with disabilities. First session sold out; limited spots left for the 2nd session!
Experience Drew Angus live at SHU Community Theatre March 21 for a powerful night of timeless rock and storytelling.
Best-selling author Claire Dederer joins Hilarie M. Sheets at Verso Fest'26 - March 28th to discuss Monsters: A Fan’s Dilemma and the ethics of art.