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Fairfield County Weekend Guide: Pure Fun, Live Music, and Comedy Without the Holiday Overload
Looking for things to do this weekend in and around Fairfield County? Fairfield After Dark has you covered! Sure, there’s plenty of holiday shopping, festive photo ops, and all things “holiday this and holiday that,” but what about some pure, no-theme-needed entertainment? You’ll be happy to know there’s plenty of that happening too. From live music and comedy shows to fun nights out with something to do, we’ve got the scoop on the best spots to enjoy a great weekend—holiday-free or not!
- Bridgeport: Trivia Night - Hub & Spoke, Black Rock(7:30pm-9:30pm)
- Fairfield: Live music with The Lamb Jam at The Seagrape Fairfield(8:30pm)
- Milford: Trivia Night - Flipside Burgers & Bar, Milford(7pm)
- Milford: Trivia Night at Tribus Beer Co.(7:30pm-9:30pm)
- ⭐Newtown: Whisper From Heaven w/ Patricia Griffin at Aquila's Nest Vineyards(6:15pm)
- Newtown: Wednesday Night Trivia at Reverie Brewing(7pm)
- Old Greenwich: "The Real" Liquid Courage LIVE at BOSCO's Bar & Grill(9pm-11pm)
- Rye, NY: Orchestra Lumos Small Spaces: The History of Jazz in 80 Minutes(7pm-8:30pm)
- Stratford: WEDNESDAY NIGHT TRIVIA AT AREA TWO(6:30pm)
- Stratford: Open Mic Night at Joey C's(7pm-10pm)
- Stamford: Trivia with MC JHype - Tiernan's, Stamford(7pm-9pm)
- Stamford: Open Mic Night at Half Full Brewery(7pm-9pm)
- ⭐Stamford: Comedians Sara Tollemache & Sean Donnelly at New York Comedy Club Stamford(7pm-10pm)
- Bethel: Trivia Night at Broken Symmetry(7pm)
- Danbury: Line Dancing LIVE at Elicit – Danbury(7pm)
- Fairfield: ETA Music LIVE at The Sinclair(8:30pm)
- Milford: Mix it Up Band LIVE at Dockside Brewery(7pm-10pm)
- Newtown: Trivia Night at Newsylum Brewing Co(6:30pm)
- ⭐Newtown: Wine, Words & Wisdom Book Club Series at Aquila's Nest Vineyards(6:30pm)
- ⭐Newtown: The Yale Whiffenpoofs & Whim n’ Rhythm comes to Edmond Town Hall(8pm-10pm)
- Norwalk: Live music with STEVEN KEITH!(5:30pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Rowayton: DEVIN DAVERSA LIVE at Sails American Grill(6pm-9pm)
- Sherman: Open Mic Night - JCC in Sherman(6:30pm-8:45pm)
- Stratford: Jukebox Bingo(6:30pm-9pm)
- ⭐Stamford: Comedian Tara Cannistraci at New York Comedy Club Stamford(7pm)
- Westport: Paul Bollenback w/ David Kikowski LIVE at Jazz FC(7:30pm-10pm)
- Westport: Live music with Billy Genuario(9pm)
- Bethel: ROVING SON LIVE at Shakedown Street Eats(6:30pm)
- Bethel: SISTER FUNK LIVE at Notch 8(8pm)
- Danbury: Go 2 Eleven LIVE at Charter Oak Brewing(7pm-9pm)
- Danbury: Good Godfrey, A Very Godfrey Christmas LIVE at Sugar Hollow Taproom(8:30pm)
- Danbury: DJ SKATE FRIDAYS at Danbury Arena(8:30pm-10:30pm)
- Danbury: Struggle Monkey LIVE at Elicit – Danbury(9pm)
- Danbury: DJ J.R LIVE at Elicit – Danbury(10pm)
- Fairfield: Hijacked LIVE at Elicit Fairfield(9pm)
- Newtown:Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm)
- ⭐Newtown: Bake Brie & Vino Night at Aquila's Nest Vineyards(6pm)
- ⭐Newtown: Jazz Winter Fest at Aquila's Nest Vineyards(6pm-9pm)
- Newtown: Rob Glassman Band LIVE at Reverie Brewing(6pm-9pm)
- ⭐Norwalk: SoNo 1420 Distillery Great Gatsby Party(5pm-10pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Norwalk: Old School 203 LIVE at 314 Beer Garden(7pm-11pm)
- Old Greenwich: The Last Hoorah LIVE at BOSCO's Bar & Grill(9pm-12am)
- Ridgefield: The North County Band with Jason Ingriselli & the Miles North LIVE at Nod Hill Brewery(7pm)
- Rowayton: Pimpineella LIVE at Sails American Grill(9pm-12am)
- Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm)
- Shelton: Tangled Vine LIVE at Pier 131(9:30pm-12am)
- Stratford: Frank Yantorno LIVE at Windmill Tavern(5pm)
- Stratford: Freestyle Holiday Dance Party LIVE at Joey C’s Boathouse(9pm-12am)
- ⭐Stamford: Comedian Yannis Pappas at New York Comedy Club Stamford(7pm-9:30pm)
- ⭐Stamford: Dave Attell at The Palace Stamford(8pm)
- Stamford: EKG LIVE at Third Place(9pm)
- Stamford: New Panic LIVE at Tiernan's Bar(9:30pm)
- Westport: Pimpinella LIVE at Black Duck Cafe(9:30pm)
- Bethel: JOE PROC LIVE at Shakedown Street Eats(6:30pm)
- Bethel: MYSTERY TRAIN LIVE at Notch 8(8pm)
- Bridgeport: Ladies Game Day at Port 5 Naval Vets(1pm-3pm)
- ⭐Fairfield: A Hometown Celebration: The Alternate Routes with Opening Act The Moonrise Cartel in The Warehouse at FTC(8pm)
- Fairfield: Black Rock Fire LIVE at Elicit Fairfield(9pm)
- Danbury: Tony & The West Siders LIVE at Charter Oak Brewing(4pm-7pm)
- Danbury: Future Tense LIVE at Sugar Hollow Taproom(8:30pm)
- Danbury: Hawkins French LIVE at Elicit – Danbury(9pm)
- Danbury: BOSCO & THE STORM LIVE at Molly Darcy(10pm)
- Danbury: DJ ILARDI LIVE at Elicit – Danbury(10pm)
- Milford: DJ Flip Band LIVE at Dockside Brewery(9pm-12am)
- New Milford: VinylCut LIVE at Houstatonic River Brewing(7pm-10pm)
- New Canaan: RETRO EXPRESS LIVE at Gates Restaurant(8:30pm-11:30pm)
- Newtown: Nick Di Maria Christmas Jazz LIVE at Reverie Brewing(12pm-3pm)
- ⭐Newtown:Jazz Winter Fest at Aquila's Nest Vineyards(1pm)
- Norwalk: Electric Wonderland at 314 Beer Garden(5pm-11pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Norwalk: Live Music Every Saturday!!(10pm)
- Old Greenwich: Meet Santa LIVE at BOSCO's Bar & Grill(3pm-5pm)
- Old Greenwich: Frankie and the Soundcats LIVE at BOSCO's Bar & Grill(9pm-12am)
- Ridgefield: 'TheDisneyPinventory' Pin Trading Event(12pm-4:30pm)
- Ridgefield: Western Skies LIVE at Nod Hill Brewery(6:30pm)
- ⭐Stamford: Comedians Paul Valdes-Rodriguez, Colin Pasquarella, Dan Kalwhite, Michele Traina at New York Comedy Club Stamford(4:30pm)
- ⭐Stamford: Comedian Yannis Pappas at New York Comedy Club Stamford(7pm-9:30pm)
- ⭐Stamford: Rock and Roll Playhouse Plays: Music of Queen & More For Kids at The Palace Theatre Stamford(12pm)
- ⭐Stamford: Julia Cole Performs Live at The Palace Theatre Stamford(8pm)
- Stamford: Almost Ablaze LIVE at Third Place by Half Full Brewery(8pm-10pm)
- Stamford: Get Lit LIVE at Tiernan's Bar(9:30pm)
- Stratford: Bad Saints LIVE at Windmill Tavern(8pm)
- Stratford: Branded Country Band LIVE at Joey C’s Boathouse(9pm-12am)
- Westport: On the Trail LIVE at Voices Cafe(8pm)
- Westport: Vertigo LIVE at Black Duck Cafe(9:30pm)
- Weston: Jane Austen’s 250th Birthday - Lecture & Dance(2pm-3:30pm)
- Bethel: ROBER FULLERTON LIVE at Shakedown Street Eats(11am)
- Danbury: The Argyle Sax Quartet LIVE at Charter Oak Brewing(3pm-5pm)
- Danbury: Tangled Vine LIVE at Sugar Hollow Taproom(4pm)
- ⭐Danbury: The Edwards Twins at The Palace Danbury Theatre(3pm)
- New Milford: Dan Sawyer LIVE at Houstatonic River Brewing(4pm-7pm)
- ⭐Newtown: Jazz Winter Fest at Aquila's Nest Vineyards(12pm)
- Newtown: Round Two LIVE at Reverie Brewing(2pm-5pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Shelton: DJ Johnny Bananas LIVE at Pier 131(11:30am-3:30pm)
- ⭐Stamford: MANNHEIM STEAMROLLER CHRISTMAS at The Palace Stamford(7pm)
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.