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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)


Westport, CT - Verso Studios, the media arm of The Westport Library, is excited to announce its first-ever Battle of the Bands , an electrifying live music event celebrating the next generation of Fairfield County talent. Taking place Saturday, January 10, in the Library’s incomparable Trefz Forum, the high-energy showcase will feature four standout teen and college-aged bands: The Breakers, Clockwork, Caravan, and MOSS . Doors open at 7 pm , with the show beginning at 8 pm . Tickets are $10 for students and $20 for general admission, and can be purchased here . More than just a concert, this interactive competition puts the outcome entirely in the hands of the audience. Attendees will vote at the end of the night to determine the winner, awarding a $500 grand prize to first place and $250 to second place. Verso Studios is dedicated to amplifying creativity, collaboration, and community, and the debut of this Battle of the Bands marks an exciting new initiative in support of local live music. The event brings together emerging artists and music fans for a night that celebrates original sound, high-energy performance, and grassroots support for the local music scene. Whether attendees come to support a favorite band or discover something new, the event promises an unforgettable experience where community engagement plays a central role. Event Details Location: Trefz Forum, The Westport Library, 20 Jesup Road, Westport, CT 06880 Doors: 7 pm Show: 8 pm Bands: The Breakers, Clockwork, Caravan, MOSS Audience-voted competition with cash prizes Tickets and additional information: https://westportlibrary.org/event/verso-studios-presents-battle-of-the-bands/

Brookfield Film Festival: A Small Town with a Big Film Legacy Brookfield, CT - Brookfield, Connecticut may be a small town, but it holds a meaningful place in the regional film community. Located in Fairfield County within the southern foothills of the Berkshire Mountains, Brookfield is bordered by Candlewood Lake and Lake Lillinonah and sits just 43 miles northeast of New York City. With a population of approximately 17,000, the town has become a welcoming hub for independent filmmakers. Now in its 18th year, the Brookfield Film Festival continues to gain momentum inside the historic Brookfield Theatre for the Arts. Sponsored by the all-volunteer Brookfield Arts Commission, the festival not only celebrates independent film, but also supports arts education. Proceeds benefit the Brookfield Arts Commission Arts Scholarship Award, presented annually to a graduating Brookfield high school senior pursuing a degree in the arts. This year’s two-day festival features four curated program blocks. Regional Indie Afternoon showcases films from Connecticut and neighboring states, followed by filmmaker Q&A discussions. Read-Through Indie Morning, presented with the Brookfield Theatre for the Arts, gives screenwriters the opportunity to hear their work read aloud and network with actors and filmmakers in a collaborative setting, complete with complimentary coffee and pastries. Shorts and to the Point highlights a handpicked selection of Oscar-nominated and award-winning short films, while Music Indie Evening features original music videos from regional artists and filmmakers. The Brookfield Film Festival takes place March 27 through March 29 at the Brookfield Theatre for the Arts, located at 184 Whisconier Road in Brookfield, CT. A $15 suggested donation supports festival programming and scholarships. Light refreshments and festival merchandise will be available throughout the weekend. With its intimate atmosphere, diverse programming, and strong community focus, the Brookfield Film Festival proves that big creative impact can come from a small town.

Stamford, Ct - Stamford Downtown is excited to announce the return of the beloved Fire & Ice Winter Festival , bringing warmth, artistry, and winter fun back to Columbus Park on Saturday, January 24, 2026, from 1:00 to 5:00 PM . A favorite seasonal tradition, Fire & Ice offers a dynamic afternoon for all ages. Visitors can gather around cozy fire pits, watch live ice sculpting demonstrations by talented professional artists, and enjoy live music throughout the park. Nearby Columbus Park restaurants will add to the experience with inviting indoor and outdoor dining options, creating a lively and welcoming winter atmosphere. This FREE community festival celebrates the best of winter in Stamford Downtown—bundled-up fun, glowing fires, sparkling ice, and shared moments. Don’t miss this signature winter event!




