Share the news!
Autumn Adventures: Fairs, Festivals & Local Fun
Fall is in full swing, and Fairfield County is buzzing with seasonal excitement this weekend! From pumpkin and apple picking to the first round of Halloween thrills, there’s no shortage of ways to soak in the season. Music lovers can enjoy live concerts across the county, comedy fans can laugh the night away, and families can explore farmers markets, brewery tastings, craft fairs, and fall festivals. Wherever your interests lie, this weekend is packed with everything we love about autumn—cozy, colorful, and full of community fun.
- Bridgeport: Josh A LIVE at Port 5(5pm-8:30pm)
- 🎪 Bristol: Bristol Mum Festival(5pm-9pm)
- Bethel: BRANDON MULLIS LIVE at Shakedown Street(6:30pm)
- Bethel: CHICAGO DAWGS at Notch 8(8pm)
- 🎪 Durham: Durham Fair(9am-10am)
- Danbury: Teddy Goldstein + Dad’s Grill LIVE at Charter Oak Brewing(6pm-8pm)
- Danbury: Ace and Friends LIVE at Sugar Hollow(8:30pm)
- Danbury: Funnel LIVE at Elicit Brewing Danbury(9pm)
- Easton: Pumpkin Patch at Silverman's Farm
- Fairfield: Rock for a cause with Tangled Vine(5:30pm)
- Fairfield: Willie Nile on StageOne at FTC(8pm)
- 🎪 Kent: Fall Festival at Connecticut Antique Machinery(10am-4pm)
- Monroe: Shay Sully LIVE at Marcello’s Italian Eatery(8pm-10pm)
- 🍻 Milford: Milford Oktoberfest(5pm-10pm)
- 🎪 Milford: St. Mary's Carnival(5pm-10pm)
- Milford: HAPPY SALLY LIVE at Stonebridge Restaurant(6:30pm)
- Mahopac, NY: Billy Joel & Elton John LIVE at Putnam County Golf Course(6:30pm)
- New Milford: The Ultimate Bangles & GoGo's Tribute Band LIVE at Housatonic River Brewing(7pm-10pm)
- 👻 New Haven: Ghosts of New Haven(7:30pm)
- 📣 Newtown: Gab Kallay Duo LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm)
- 📣 Newtown: Wine and Wheels Car Show at Aquila's Nest Vineyards(6pm)
- 📣 Newtown: Brownies & Wine Pairing at Aquila's Nest Vineyards(6pm)
- Newtown: Crossroad Crooks LIVE at Reverie Brewing(6pm-9pm)
- Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm)
- 🎪 Newtown: Newtown Arts Festival(7pm-10pm)
- Newtown: DJ JR In the Mix at Perfusion Bar(8pm-11pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Port Chester, NY: Johnny Marr w/Trace Mountains LIVE at The Capitol Theatre(8pm)
- Pawling, NY: Strange Magic NY LIVE at Daryl's House Restaurant & Live Music Club(8pm)
- Ridgefield: Hitch & the Giddyup LIVE at Nod Hill Brewery(6:30pm)
- Redding: Cat Lines LIVE at The Redding Roadhouse(7pm-10pm)
- Rowayton: 41 North Band LIVE at Sails American Grill(9:30pm-12am)
- Shelton: No Strings Attached LIVE at Pier131(9:30pm-12am)
- Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm)
- Stratford: Sentinel Salt LIVE at Windmill Restaurant(5pm)
- Stratford: Dawn & Greg LIVE at Outriggers(5:30pm-8:30pm)
- Stratford: SAPPHIRE LIVE at Blackbird's Nest(6pm)
- Stratford: Dueling Pianos Night at Two Roads Brewing(6:30pm-9:30pm)
- Stratford: Sentinel Salt LIVE at Windmill Restaurant(8pm)
- Stratford: The Wankers LIVE at Joey C’s Boathouse(8pm-12am)
- 📣 🤣 Stamford: Comedian Dustin Nickerson ("The Tonight Show", "After Midnight") at New York Comedy Club Stamford(7pm-9:30pm)
- Stamford: Dive Bar Confessional LIVE at Bobby V's Restaurant(7pm-10pm)
- 📣 Stamford: The Electric Light Orchestra at The Palace Stamford(8pm)
- Stamford: The Tub Band LIVE at Tiernan's(9:30pm)
- Westport: Green Eyed Lady LIVE at Black Duck Cafe(9:30pm)
- 🍎 West Haven: West Haven Apple Festival(4pm-8pm)
- Westport: The Last Minutemen LIVE at Walrus Alley(7:30pm-11pm)
- Woodbury: The Rakes LIVE at Woodbury Brewing Company(8:30pm)
- Armonk, NY: Armonk Outdoor Art Show(10am-5pm)
- 🍻 Bridgeport: Oktoberfest at Berlinetta Brewing Co(1pm-9pm)
- Bridgeport: The Dharma Bums LIVE at BRYAC(10pm)
- Bethel: MICHAEL BRAM LIVE at Shakedown Street(6:30pm)
- Bethel: MUDDY RIVER BLUES LIVE at Notch 8(8pm)
- 🎪 Durham: Durham Fair(9am-10pm)
- Danbury: Iris Lies + Smash Bros Truck LIVE at Charter Oak Brewing(6pm-8pm)
- 📣 🤣 Danbury: The Uncle Louie Variety Show at The Palace Danbury(8pm)
- Danbury: Sugar House Band w/Touro Band at Sugar Hollow(8:30pm)
- Danbury: GOOD TIME CHARLIES LIVE at Molly Darcy(9pm)
- Darien: DIRTY WATER DOGS LIVE at The Goose(9pm-12am)
- Easton: Pumpkin Patch at Silverman's Farm
- Fairfield: The Moonrise Cartel w/ Charlotte Roth and the Big Drama LIVE at StageOne FTC(7pm)
- 🍻 Hunter, NY: OKTOBERFEST at Hunter Mountain(11am-6pm)
- 🎪 Kent: Fall Festival at Connecticut Antique Machinery(10am-4pm)
- 🎪 Lebanon: 27th Annual Connecticut Renaissance Faire(10:30am-6pm)
- 🎪 Milford: St. Mary's Carnival(1pm-10pm)
- 🍻 Milford: Milford Oktoberfest(2pm-10pm)
- 🎪 New London: New London Harvest Festival at the Old Town Mill(11am-3pm)
- New Milford: Candy-O LIVE at Housatonic River Brewing(7pm-10pm)
- New Canaan: VERTIGO LIVE at Gates Restaurants and Bar(8:30pm)
- 🍂 Newtown: Fall Festival at Castle Hill Farm(10am-5pm)
- 🎪 Newtown: Newtown Arts Festival(11am-5pm)
- 📣 Newtown: Color Between the Wines at Aquila's Nest Vineyards(12pm)
- 📣 Newtown: Croissants & Wine Brunch at Aquila's Nest Vineyards(12pm)
- 📣 Newtown: Mini Cheesecakes & Sweet Wines Pairing at Aquila's Nest Vineyards(12pm)
- 📣 Newtown: Frandango LIVE at Aquila's Nest Vineyards(2:30pm-5:30pm)
- 📣🤣 Newtown: Comedy Night at Aquila's Nest Vineyard(7pm)
- 🍻 Newtown: Oktoberfest at Reverie Brewing Co(12pm-10pm)
- Newtown: Hitch & the Giddy Up LIVE at Newsylum Brewing Co(3pm-6pm)
- Newtown: Orb Mellon LIVE at Perfusion Bar(8pm-11pm)
- Norwalk: SoNo Saturday Market(10am-1pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Pawling, NY: John Fries Duo LIVE at Daryl's House Restaurant & Live Music Club(12pm)
- Pawling, NY: Romeo Delight LIVE at Daryl's House Restaurant & Live Music Club(8pm)
- Ridgefield: The Fairfield County Brass Quintet LIVE at Nod Hill Brewery(1pm)
- Ridgefield: Nathaniel Hintz LIVE at Nod Hill Brewery(5pm)
- 🎪 Redding: Artisan Fair - First Church of Christ Congregational Artisan Fair(10am-4:30pm)
- Redding: Pimpinella LIVE at Milestone(9pm-12am)
- Shelton: Suck' r Punch LIVE at Stormy's(8:30pm)
- Sherman: Mike Latini - Mike & The Mysteries Ride Again Concert LIVE at JCC in Sherman(7pm-9pm)
- 🍻 Stamford: Oktoberfest Weekend – Axe Throwing at Third Place by Half Full Brewery(2pm-6pm)
- Stamford: Riverbank Ramble(2pm-9pm)
- Stamford: Live Music by Whiskey & Rye at The Beer Garden (Shippan Landing)(5pm-8pm)
- 📣 🤣 Stamford: Comedian Dustin Nickerson ("The Tonight Show", "After Midnight") at New York Comedy Club Stamford(7pm-9:30pm)
- 📣 Stamford: Julia Cole at The Palace Stamford(8pm)
- Stamford: Ulysses and the Leftys LIVE at Tiernan's(9:30pm)
- Stratford: Dawn & Greg LIVE at Outriggers Restaurant(5:30pm-8:30pm)
- Stratford: SHEFFIELD DRIVE LIVE at Blackbird's Nest(6pm)
- Stratford: Preacher Dogs LIVE at Windmill Restaurant(8pm)
- Stratford: Freestyle Night LIVE at Joey C’s Boathouse(8pm-12am)
- 🍻 Westport: Oktoberfest 2025 LIVE at Walrus Alley(12:30pm-11:30pm)
- Westport: Alligator LIVE at Walrus Alley(7:17pm-8:18pm)
- Westport: Underdogs LIVE at Black Duck Cafe(9:30pm)
- 🎪 West Haven: West Haven Apple Festival(10am-8pm)
- Woodbury: Anchor Management LIVE at Woodbury Brewing Company(8:30pm)
- Woodbury: Juice Box LIVE at Woodbury Brewing Company(8:30pm)
- Armonk, NY: Armonk Outdoor Art Show(10am-5pm)
- Bethel: ERIK RABASCA LIVE at Shakedown Street(12pm)
- Bethel: TOURO BAND LIVE at Notch 8(5pm)
- 🎪 Bristol: Bristol Mum Festival(12pm-6pm)
- Bridgeport: The Signature Duo LIVE at Port 5(3pm)
- Bridgeport: Laughin’ Bones LIVE at BRYAC(6pm)
- 🎪 Durham: Durham Fair(9am-6pm)
- Danbury: The Angry O’Haras + Blangn Thai Bistro Truck LIVE at Charter Oak Brewing(2:30pm-5:30pm)
- Easton: Pumpkin Patch at Silverman's Farm
- Fairfield: The Cactus Blossoms LIVE at StageOne FTC(8pm)
- 🍻 Hunter, NY: OKTOBERFEST at Hunter Mountain(11am-6pm)
- 🎪 Kent: Fall Festival at Connecticut Antique Machinery(10am-4pm)
- 🎪 Lebanon: 27th Annual Connecticut Renaissance Faire(10:30am-6pm)
- 🎪 Milford: St. Mary's Carnival(1pm-5pm)
- New Milford: Lost Rebel LIVE at Housatonic River Brewing(4pm-7pm)
- 🍂 Newtown: Fall Festival at Castle Hill Farm(10am-5pm)
- 🎪 Newtown: Newtown Arts Festival(11am-5pm)
- 📣 Newtown: Nineteen89 - A Tribute to Taylor's Music at Aquila's Nest Vineyards(12pm)
- 📣 Newtown: Sip & Shimmy Belly Dancing at Aquila's Nest Vineyards(12pm-2pm)
- 📣 Newtown: On the Road Again LIVE at Aquila's Nest Vineyards(2pm-5pm)
- Newtown: R.A.E. LIVE at Newsylum Brewing Co(2pm-5pm)
- Newtown: Round Two LIVE at Reverie Brewing(2pm-5pm)
- 📣 Newtown: Albanian Live Music with Vedat Ademi at Aquila's Nest Vineyards(5pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Pawling, NY: David Powers LIVE at Daryl's House Restaurant & Live Music Club(12pm)
- Pawling, NY: Awaken LIVE at Daryl's House Restaurant & Live Music Club(7pm)
- Shelton: Fake ID LIVE at Spotted Horse(4pm)
- Stratford: Paper Suns LIVE at Two Roads(2pm-4:30pm)
- Stratford: Rahsaan Langley Project LIVE at Joey C’s Boathouse(3pm-7pm)
- Stratford: BILLY GENUARIO LIVE at Blackbird's Nest(5pm)
- 📣🤣 Stamford: Comedian Jason Ellis at New York Comedy Club Stamford(7pm)
- 📣 🤣 Stamford: Comedy Jackpot Competition at New York Comedy Club Stamford(4pm)
- Westport: Bluegrass Brunch LIVE at Walley Alley(12pm-2:30pm)
- Westport: MIHALI * Full Band Show * w/ Night Zero and Residual Groove at Levitt Pavilion(4:30pm)
- 🍎 West Haven: West Haven Apple Festival(12pm-5pm)
- Weston: Summer Sundays at Weston History & Culture Center(1pm-4pm)
- Woodbury: Liquid Love LIVE at Woodbury Brewing Company(2pm)
Snowy weather calls for adventure. Fairfield After Dark rounds up the best ski resorts near Connecticut for winter fun.
Michael Jackson’s iconic hits come alive with Who’s Bad, the ultimate MJ tribute, live at The Palace Theatre Stamford on January 16.
Experience A Kenny Chesney Tribute with Pirate Flag live at The Palace Theatre Stamford on January 17. High-energy country hits—tickets on sale now.
GRAMMY winners The Band Perry perform Jan 10 at The Palace Theatre Stamford, joined by rising artist Stephanie Ryann.
Stamford, CT - Looking for a fun, family-friendly event in Stamford this holiday season? The Canine Stars is bringing its high-energy stunt dog show to The Palace Theatre Stamford on Sunday, December 28 , and Fairfield After Dark is giving one lucky family the chance to win a free family four-pack of tickets . The Canine Stars is a nationally touring, fan-favorite live show featuring talented rescue dogs performing incredible stunts, agility tricks, and crowd-pleasing routines. This interactive performance is perfect for kids, parents, and dog lovers of all ages, making it one of the best family events in Fairfield County this winter. Before the show, ticket holders can attend a special pre-show dog adoption event from 1:00–3:00 PM , where families can meet adoptable dogs and connect with local rescue organizations. It’s a heartwarming way to support animal adoption while enjoying a memorable day out. Fairfield After Dark has secured four tickets for one lucky family to attend this exciting live performance at The Palace Theatre Stamford. 👉 To enter to win, click the link: ENTER TO WIN Prefer not to wait? Tickets to Canine Stars at The Palace Theatre Stamford are available now and are expected to sell quickly. Whether you enter the giveaway or purchase tickets, this is a must-see holiday event for families in 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)