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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)
Experience the magic of Mannheim Steamroller Christmas on December 7 at The Palace Theatre Stamford. A festive night of timeless holiday music and tradition awaits.
Discover Fairfield County’s top holiday events, including Newtown’s Holiday Festival, sip & shops, tree lightings, festive shows, and Repeal Day celebrations.
Country fans, mark your calendars — Julia Cole is coming to The Palace Theatre Stamford on December 6, 2025, and this is one high-energy show you won’t want to miss. Please note: the originally scheduled September 27 & 28 performances have been rescheduled to December 6 , and all tickets from those dates will be honored. The show has also moved from the UpStage to the Mainstage and will remain general admission . Nashville recording artist Julia Cole continues her rapid rise as one of country music’s most empowering and influential new voices. With over 500 million streams , more than 2 million social followers , and a debut on the Grand Ole Opry , Julia’s star power is undeniable. She’s been named a CMT Next Woman of Country and featured on CMT, SiriusXM, Circle TV, CBS, The CW, and more. Blending authentic country storytelling with real-life moments, Julia’s musical journey began singing the national anthem at her high school volleyball games—eventually performing for NFL, MLB, MLS, NASCAR, and ESPN crowds of 75,000. She’s toured internationally, opening for major acts like Dierks Bentley, Dan + Shay, Jon Pardi, Carrie Underwood, Kenny Chesney, Kane Brown, The Chainsmokers, Lee Brice and more. 🎟️ Tickets are on sale now! Purchase here: palacestamford.org Don’t miss Julia Cole live at The Palace Theatre Stamford’s Mainstage!
Celebrate Repeal Day at SONO 1420 with a Great Gatsby Party featuring Prohibition cocktails, a Land & Sea menu, and live jazz from DTHREE Music.
Enjoy five live jazz performances, gourmet food trucks, and cozy vibes at Aquila’s December Jazz Fest in Newtown, CT. Tickets just $20 for the full weekend.
Paul Virzi takes the stage at Edmond Town Hall on December 12 for a night of sharp wit, bold humor, and unforgettable stand-up comedy.