Holiday Shopping Done? Unwind With This Week’s Best Happenings Around Fairfield County

All your holiday shopping is done—now it’s time to relax and enjoy the week ahead. Whether you’re in the mood for a lively Trivia Night, a Sip & Learn French experience, or a night of laugh-out-loud comedy, Fairfield After Dark has you covered. We’ve curated our weekly happenings to keep you entertained through Sunday, with something happening every day in and around Fairfield County. Take a look at what’s on tap and start planning your week of fun.  And Enter To  Win 2 Tickets to see StevieMac: A Fleetwood Mac and Stevie Nicks Experience here.  

Wednesday 17th,2025 

• Bridgeport: Trivia Night - Hub & Spoke, Black Rock(7:30pm-9:30pm) 
• Fairfield: Trivia - Flipside Burgers & Bar, Fairfield(7pm-9pm) 
• 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) 
• Milford: Laugh Tracks Standup Comedy – John Bennett(8pm-10pm) 
• Newtown: Sip n Learn French Class at Aquila's Nest Vineyards(6pm)  
• Newtown: Sips & Sparks Singles Mixer at Aquila's Nest Vineyards(7pm) 
• Newtown: Wednesday Night Trivia at Reverie Brewing(7pm) 
• Stratford: WEDNESDAY NIGHT TRIVIA AT AREA TWO(6:30pm) 
• Stratford: Open Mic Night at Joey C's(7pm-10pm) 
• Stamford: Comedians Alex Pavone, Chris Scopo, Tocarra Elise, Jason Choi at New York Comedy Club Stamford (7:00pm) 
• Stamford: Trivia with MC JHype - Tiernan's, Stamford(7pm-9pm) 
• Stamford: Open Mic Night at Half Full Brewery(7pm-9pm) 

Thursday 18th,2025 

• Bethel: Trivia Night at Broken Symmetry(7pm) 
• Bridgeport: Hurley Hour LIVE at Bryac(6pm)  
• Bridgeport: Vicky & Adam LIVE at The Castle Black Rock(7pm-10pm) 
• Bridgeport: Party With Friends at Bryac(9pm) 
• Danbury: Line Dancing LIVE at Elicit - Danbury(7pm) 
• Danbury: Thursday Open Jam with Fuzz LIVE at Sugar Hollow Taproom(8pm) 
• Fairfield: Tangled Vine LIVE at The Sinclair(8:30pm) 
• Milford: Young Dan & Jumpin Johnny LIVE at Cafe Atlantique(5pm-8pm) 
• Newtown: Chocolate Fondue Dip & Sip at Aquila's Nest Vineyards(6pm) 
• Newtown: Trivia Night at Newsylum Brewing Co(6:30pm) 
• 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)  
• Ridgefield: Chris Cavaliere LIVE at Nod Hill Brewery(6:30pm) 
• Rowayton: Henry Jones LIVE at Sails American Grill(6pm-9pm)  
• Sherman: Open Mic Night - JCC in Sherman(6:30pm-8:45pm) 
• Shelton: Happy Sally LIVE at Pier 131(7pm-10pm) 
• Stratford: Jukebox Bingo(6:30pm-9pm) 
• Westport: Live music with Billy Genuario(9pm) 

Friday 19th,2025 

• Bethel: IRIS LIES LIVE at Notch 8(8pm) 
• Bridgeport: Style Acoustic LIVE at The Castle Black Rock(8pm-11pm) 
• Bridgeport: Otis & The Hurricanes LIVE at Bryac(9:30pm) 
• Danbury: Snake Dog LIVE at Sugar Hollow Taproom(8:30pm) 
• Danbury: DJ SKATE FRIDAYS at Danbury Arena(8:30pm-10:30pm) 
• Danbury: Melodus LIVE at Elicit - Danbury(9pm) 
• Danbury: Sex & Candy LIVE at Elicit - Danbury(9pm) 
• Danbury: DJ Roc LIVE at Elicit - Danbury(10pm) 
• Fairfield: Hawkins French LIVE at Elicit Fairfield(9pm) 
• New Milford: Pimpinella LIVE at Houstatonic River Brewing(7pm-10pm)  
• Milford: Ode to Rosie LIVE at Cafe Atlantique(6:30pm-9:30pm) 
• Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm) 
• Newtown: Scratch LIVE at Reverie Brewing(6pm-9pm) 
• Newtown: Mike Super Magic & Illusion at Edmond Town Hall(7pm) 
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) 
• Norwalk: Jukebox Radio LIVE at 314 Beeer Garden(7:30pm-10:30pm) 
• Old Greenwich: Chasing Romeo LIVE at BOSCO's Bar & Grill(9pm-12am) 
• Port Chester, NY: Pigeons Playing Ping Pong with Spafford LIVE at Capitol Theatre - Port Chester, NY(7:30pm) 
• Ridgefield: Traditional Irish Session LIVE at Nod Hill Brewery(6pm)  
• Rowayton: Billy G and Friends LIVE at Sails American Grill(9pm-12am) 
• Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm) 
• Stamford: Comedian Michael Blaustein at New York Comedy Club(7pm-9:30pm) 
• Stamford: Dive Bar Confessional LIVE at Bobby V's Stamford(7pm-10pm) 
• Stamford: StevieMac Fleetwood Mac Tribute at The Palace Theatre Stamford(8pm) 
• Stamford: Captain Obvious LIVE at Third Place by Half Full Brewery(8pm-10pm) 
• Stamford: Bad Management LIVE at Tiernan's Bar(9:30pm)  
• Stratford: Flannel Clad Masses LIVE at Windmill Tavern(8pm) 
• Stratford: Latin Night Afinke Christmas Party LIVE at Joey C’s Boathouse(9pm-12am)  
• Westport: Green Eyed Lady LIVE at Black Duck Cafe(9:30pm) 

Saturday 20th,2025 

• Bethel: SETH ASAM LIVE at Shakedown Street Eats(6:30pm) 
• Bethel: JUNK LIVE at Notch 8(8pm)  
• Bridgeport: Live Music + Poetry at “Corridor for Ghosts and Heralds” Exhibition(7pm-9pm)  
• Bridgeport: Greater Bridgeport Symphony Presents Holiday Quintessence December 20 at The Klein Memorial Auditorium in Bridgeport, CT(7:30pm-10pm) 
• Bridgeport: Ruff Dogs LIVE at The Castle Black Rock(8pm-11pm) 
• Bridgeport: Grateful Ghost LIVE at Bryac(10pm) 
• Danbury: Sugar House Winter Show w/ Chowdah Music LIVE at Sugar Hollow Taproom(7:30pm) 
• Danbury: FDR DRIVE LIVE at Molly Darcy(10pm) 
• Darien: FAN FICTION LIVE at The Goose(9pm-12am) 
• Fairfield: Beggars & Choosers LIVE at Elicit Fairfield(9pm) 
• Milford: Cintia Maio/ Sydney DiStefano (DOUBLE HEADER) LIVE at Cafe Atlantique(6:30pm-9:30pm) 
• New Canaan: Mind the Gap LIVE at Gates Restaurant(8:30pm-11:30pm) 
• New Milford: The Outcrops LIVE at Houstatonic River Brewing(7pm-10pm) 
• Newtown: Shawn Taylor LIVE at Aquila's Nest Vineyards(1pm-4pm) 
• Newtown: Silent Disco Ugly Sweater Party at Aquila's Nest Vineyards(6pm)  
• Newtown: Mike & Ike LIVE at Newsylum Brewing Co.(3pm-6pm) 
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)  
• Norwalk: For Legal Reasons LIVE at 314 Beeer Garden(7:30pm-10:30pm) 
• Norwalk: Live Music Every Saturday(10pm)  
• Old Greenwich: Kovac Brothers Winter Fest LIVE at BOSCO's Bar & Grill(9pm-12am)  
• Port Chester, NY: Pigeons Playing Ping Pong with Great Blue LIVE at Capitol Theatre - Port Chester, NY(7:30pm) 
• Stamford: Comedian Michael Blaustein at New York Comedy Club(7pm-9:30pm)  
• Stamford: Little River Band at The Palace Stamford(8pm) 
• Stamford: The Proper Villains LIVE at Tiernan's Bar(9:30pm) 
• Stratford: Bad Mannerz LIVE at Windmill Tavern(8pm) 
• Stratford: Bernadettes Christmas Party LIVE at Joey C’s Boathouse(9pm-12am) 
• Westport: Shell Shockt LIVE at Black Duck Cafe(9:30pm) 

Sunday 21st,2025 

• Bethel: BRUNCH with LORRAINE MCGUIRE LIVE at Shakedown Street Eats(11am) 
• Bridgeport: Stephen Capalbo LIVE at The Castle Black Rock(5pm-8pm) 
• Bridgeport: The Red Planet LIVE at Bryac(6pm) 
• Milford: Dan Watson LIVE at Dockside Brewery(2pm-5pm) 
• New Milford: Seth Adam LIVE at Houstatonic River Brewing(4pm-7pm) 
• Newtown: Local Cheese & Wine Pairing at Aquila's Nest Vineyards(12pm) 
• Newtown: Jailhouse LIVE at Reverie Brewing(2pm-5pm) 
• Newtown: Comedy Night at Aquila's Nest Vineyards(5pm) 
• Newtown: An Irish Christmas with Andy Cooney comes to Edmond Town Hall(7pm-9pm) 
• Norwalk: Jazz Brunch LIVE at Odeen's Restaurant(12pm) 
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) 
• Shelton: DJ Revuelo LIVE at Pier 131(11:30am-3:30pm) 
• Stamford: Comedian Michael Blaustein at New York Comedy Club (NEW SHOW ADDED)(4:30pm)