Stroll, Shop & Savor: Holiday Markets and Festivals Happening This Weekend!

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)

With just one week to go until Christmas , who’s still on your gift list? Or maybe you’re checking off the final holiday shows, festive outings, and family fun before the big day arrives. As the countdown continues, there are still plenty of ways to celebrate — and a few perfect last-minute gift ideas to make your shopping easy. 🎁 Pro tip: Gift cards from our local favorites make excellent stocking stuffers, teacher gifts, host gifts, or “just because” surprises — and they support the businesses that keep Fairfield County vibrant year-round. For the past 16 years , Fairfield After Dark has proudly delivered weekly happenings across Fairfield County , made possible by the incredible support of our community partners and sponsors. When you support them, you’re helping us continue to highlight the best of where we live, work, and play. ❤️ Thank You to Our Amazing Sponsors, Community Partners & Friends We are deeply grateful to the local businesses, community partners, and friends who help make Fairfield After Dark possible. Your continued support over the years is what allows us to share weekly happenings and highlight the best of Fairfield County. This holiday season, many of our sponsors are also offering fantastic gift card options , making it easy to shop local while giving meaningful experiences. Thank you to: Aquila’s Nest Vineyards Avon Theatre CityCenter Danbury ConnectFairfield The Palace Danbury Theatre Edmond Town Hall Fairfield Theatre Company The Palace Theatre Stamford New York Comedy Club Stamford Stamford Downtown Special Services District Sono 1420 America’s Maritime Distillery Sullivan County Visitors Association Westport Downtown Association And don’t forget — we have two exciting giveaways coming up : StevieMac Concert tickets and The Canine Stars . Be sure to sign up for our weekly newsletter so you don’t miss out on these giveaways or the many incredible shows and concerts happening across Fairfield County in 2026. Wednesday 17th,2025 Essex: 2025 NORTH POLE EXPRESS - The Essex Steam Train(4pm) Milford: Menorah Lighting on the West Haven Green!(4:30pm-5:30pm) Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm) Wilton: Wilton Great Trains Holiday Show(10am-4pm) Thursday 18th,2025 Milford: The Grinch Himself & viewing Party of the Grinch Movie at Dockside!(6pm) Milford: Grinch Trivia at Dockside!(7pm) Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm) Wilton: Wilton Great Trains Holiday Show(10am-4pm) Friday 19th,2025 Milford: Welcome to Santa Claus(7:30pm) Newtown: Christmas with the Celts Dance Show at Aquila's Nest Vineyards(6:30pm) Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm) Norwalk: The Ultimate Holiday Market OnWashington, Shop-Sip-Swing(5pm-9pm) Sherman: Wreck the Halls at The Sherman Players(8pm) Stratford: Latin Night Afinke Christmas Party LIVE at Joey C’s Boathouse(9pm-12am) Stamford: Rudolph, with a special appearance by Rudolph!(5pm) Wilton: Wilton Great Trains Holiday Show(10am-4pm) Weston: 1940s Christmas Tours of the Coley House(6pm -7:15pm) & (7:30pm - 8:45pm) Saturday 20th,2025 Essex: 2025 NORTH POLE EXPRESS - The Essex Steam Train(4pm) East Haven: Breakfast with Santa at the Shore Line Trolley Museum(8:30am-10:30am) Greenwich: Holiday Happenings & Movie Night at Bendheim Western Greenwich Civic Center(5pm) Mamaroneck, NY: Nutcracker Dream LIVE at The Emelin Theatre(1:30pm & 5pm) Milford: Welcome to Santa Claus(2pm-5:30pm) Milford: SantaCon at Stonebridge Restaurant(8pm) Newtown: Yuletide Magic: Carolers & Santa Visit at Aquila's Nest Vineyards(12pm) Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(10pm-5pm) Norwalk: The Ultimate Holiday Market OnWashington, Shop-Sip-Swing(12pm-7pm) ’ Redding: "A Very Massive Christmas" at The Redding Roadhouse(6pm-9pm) Sherman: Wreck the Halls at The Sherman Players(8pm) Stratford: Bernadettes Christmas Party LIVE at Joey C’s Boathouse(9pm-12am) Weston: 1940s Christmas Tours of the Coley House(4:30pm - 5:45pm) & (6pm - 7:15pm) & (7:30pm - 8:45pm) Wilton: Wilton Great Trains Holiday Show(10am-4pm) Sunday 21st,2025 Mamaroneck, NY: Nutcracker Dream LIVE at The Emelin Theatre(1:30pm & 5pm) Milford: Welcome to Santa Claus(2pm) Monroe: Brunch with Santa at Marcello's Italian Eatery(11:30am-3pm) Newtown: An Irish Christmas with Andy Cooney comes to Edmond Town Hall(7pm-9pm) Norwalk: Holiday Gift Show 2025 at Rowayton Arts Center(12pm-5pm) Norwalk: The Ultimate Holiday Market OnWashington, Shop-Sip-Swing(12pm-5pm) New Haven: SantaCon in New Haven(11:30am) Redding: Georgetown Holiday Festival(11am-3pm) Stratford: Brunch with Santa at Area Two Experimental Brewing(10am-2pm) Stamford: Santa's Circus at The Palace Stamford(6pm) Wilton: Wilton Great Trains Holiday Show(10am-4pm)

Win the Ultimate StevieMac Holiday Bundle from FairfieldAfterDark, including show tickets, a StevieMac tee, and the iconic Buckingham Nicks vinyl.

The Canine Stars bring their thrilling stunt dog show to The Palace Theatre Stamford on Dec. 28. A high-energy, family-friendly performance you won’t want to miss.

Explore this week’s best Fairfield County entertainment, from live music and comedy to trivia nights, open mic events, and more fun things to do around the region.