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Fall Festivals & Concerts Around Fairfield County This Weekend
🍂 Fall is here, and Fairfield County is buzzing with live music, food festivals, and family-friendly fun! Whether you’re craving lobster rolls by the beach, rocking out to a live concert, or enjoying classic carnival rides, there’s something for everyone this weekend. Mark your calendars — here are the can’t-miss events from Wednesday, September 17 through Sunday, September 21.
- 📣Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)
- 📣 Bridgeport: Sean O'Reilly Band LIVE at Park City Music Hall(7pm)
- Fairfield: Mixtape Match at Elicit Brewing Fairfield(7pm)
- Fairfield: Rose City Band w/ Wet Tuna LIVE at StageOne FTC(8pm)
- 📣 Newtown: Ceremony & Sound: A Sacred Gathering at Aquila's Nest Vineyards(6pm)
- 📣 Newtown: Small Business Social at Aquila's Nest Vineyards(6pm)
- 📣 Newtown: Unapologetically Dream Big Workshop at Aquila’s Nest Vineyards(6pm)
- Norwalk: Trivia Night at 314 Beer Garden(7pm-9pm)
- 📣Stamford: Open Play Chess in Veterans Memorial Park – Stamford(12pm-2pm)
- 📣 Stamford: First Annual Connecticut Comedy Competition at New York Comedy Club Stamford(7pm)
- Westport: Art in the Barn! at Westport Country Playhouse(12pm-4pm)
- 📣Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)
- Bridgeport: Cruise Night at Port 5 - Assoc. of Naval Veterans(5pm)
- Bridgeport: Hurley Hour LIVE at BRYAC(6pm)
- Bridgeport: Party with Friends LIVE at BRYAC(9pm)
- Bethel: Open Mic Night at Molten Java(7pm-9pm)
- Danbury: Line Dancing at Elicit Brewing Danbury(7pm)
- Danbury: Thursday Open Jam w/ Sugar House at Sugar Hollow Taproom(8pm-11pm)
- Fairfield: Wine on the Water to benefit The Friends of the Bigelow Center for Senior Activites(5pm-7pm)
- Fairfield: Tangled Vine at THE SINCLAIR(8:30pm)
- Milford: Night Market returns to Milford(5pm-9pm)
- New Milford: Struggle Monkey at Rock the Block Summer Concerts(4pm-6pm)
- 📣 Newtown: Trivia Night at Newsylum Brewing Co(6:30pm)
- 📣 Newtown: Ponies and Wine Time at Aquila's Nest Vineyards(5pm)
- 📣 Newtown: What’s Good Duo LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm)
- Norwalk: Live music with STEVEN KEITH(5:30pm-8:30pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Ridgefield: Old Bob LIVE at Nod Hill Brewery(6:30pm)
- Stratford: Jukebox Bingo(6:30pm-9pm)
- 📣 Stamford: That's Fair Comedy at New York Comedy Club Stamford(7pm)
- Shelton: Beginner-Friendly Dance Lessons(7:30pm-9pm)
- Weston: Summer Thursdays at Weston History & Culture Center(1pm-4pm)
- 📣Westport: Yale Professor Akhil Reed Amar on ‘Born Equal: Remaking America’s Constitution’at Westport Library(7-8pm)
- Westport: David Hazeltine Quintet LIVE at Jazz FC(7:30pm-10pm)
- 📣Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)
- Bridgeport: Andrew Ibarra LIVE at Port 5(5pm-8:30pm)
- Bridgeport: Sugar House LIVE at BRYAC(10pm)
- Bethel: BluesyLand LIVE at Broken Symmetry(6pm)
- Bethel: BARRY from BONE DRY LIVE at Shakedown Street(6:30pm)
- Bethel: OKTOBERFEST at Broken Symmetry(6:30pm)
- Bethel: GRAVITY FEED LIVE at Notch 8(8pm)
- Danbury: Southern Desperation LIVE at Sugar Hollow Taproom(8:30pm)
- Danbury: Hijacked LIVE at Elicit Brewing Danbury(9pm)
- Derby: Anthony David LIVE at Badsons Beer(6pm-9pm)
- Fairfield: Kyle Hollingsworth Band w/ The Jauntee LIVE at StageOne FTC(7:30pm)
- Fairfield: Kathleen Edwards LIVE at The Warehouse FTC(8pm)
- Fairfield: Flannel Clad Masses LIVE at Elicit Brewing Fairfield(9pm)
- Milford: Milford Irish Festival at Fowler Field(5pm-10pm)
- New Milford: On The Rocks LIVE at Housatonic River Brewing(7pm-10pm)
- 📣 Newtown: Llamas and Llibations at Aquila's Nest Vineyards(5:30pm)
- 📣 Newtown: Bob Curiano LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm)
- 📣 Newtown: Chocolate Fondue Dip & Sip at Aquila's Nest Vineyards(6pm)
- 📣 Newtown: Friends & Family Glow Night in the Vines(6pm)
- Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm)
- 📣Newtown: Fall Carnival - Newtown Parks and Rec(6pm-10pm)
- Newtown: Ralph Judson Jazz Quartet LIVE at Perfusion Bar(8pm-11pm)
- 📣 Norwalk: Bittersweet Descent LIVE at SONO 1420(6pm-9pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Norwalk: THE JOHN CUTRONE TRIO Josie & Tony's(7pm-9pm)
- Old Greenwich: That’s What She Said LIVE at Bosco's Bar and Grill(9pm-12am)
- Ridgefield: Ian Tait & Friends LIVE at Nod Hill Brewery(6:30pm)
- Rowayton: Billy G and Friends LIVE at Sails American Grill(9:30pm-12am)
- Shelton: Seth Adam at Jones Winery — Season Finale!(5–7pm)
- Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm)
- Stratford: Dawn & Greg LIVE at Outriggers(5:30pm-8:30pm)
- Stratford: Category 5 LIVE at Joey C’s Boathouse(8pm-12am)
- 📣 Stamford: Comedian Ivan Decker at New York Comedy Club Stamford(7pm-9:30pm)
- Stamford: 80 Proof LIVE at Bobby V's Restaurant(7pm-10pm)
- 📣 Stamford: Parker Barrow at The Palace Stamford(8pm)
- Stratford: Pretty Nasty LIVE at Windmill Restaurant(8pm)
- Stamford: The Proper Villains LIVE at Tiernan's(9:30pm)
- 📣 Westport: Owen Daniel (Solo) at Music on Church Lane(6:00pm – 9:00pm)
- Westport: Art in the Barn! at Westport Country Playhouse(12pm-4pm)
- Westport: Symphonic Bodega LIVE at Walrus Alley(7:30pm-10:30pm)
- Westport: Not My Problem LIVE at Black Duck Cafe(9:30pm)
- Woodbury: Halen LIVE at Woodbury Brewing Company(8:30pm)
- 📣Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)
- Bridgeport: Tyrone Shoelaces LIVE at BRYAC(10pm)
- Bethel: OKTOBERFEST at Broken Symmetry(2pm-6:30pm)
- Bethel: Tangled Vine & Alex Cano LIVE at Broken Symmetry(6pm)
- Bethel: JUSTIN VIRGA LIVE at Shakedown Street(6:30pm)
- Bethel: HIT 'N RUN LIVE at Notch 8(8pm)
- 📣Danbury: 2025 Greater Danbury Irish Festival(12pm-10pm)
- Danbury: Milo’s Mojo LIVE at Charter Oak Brewing(5pm-7pm)
- 📣 Danbury: 1 WILD NIGHT - Bon Jovi Tribute at The Palace Danbury Theatre(7:30pm)
- Danbury: Faster Things - Allman Brothers Tribute @ Sugar Hollow(8pm-11pm)
- Danbury: BADFOOT LIVE at Elicit Brewing Danbury(9pm)
- Danbury: SEEING RED LIVE at Molly Darcy(10pm)
- Darien: TOUCHDOWN BOYS LIVE at The Goose(9pm-12am)
- Fairfield: Kendra Morris LIVE at StageOne FTC(8pm)
- Lebanon: 27th Annual Connecticut Renaissance Faire(10:30am-6pm)
- 📣Milford: Milford Lobster Roll Festival(11am-7pm)
- Milford: Milford Irish Festival at Fowler Field(11am-1pm)
- Milford: Oktoberfest at Dockside LIVE at Dockside Brewery(11:30am)
- Milford: PRESENCE (LED ZEPPELIN TRIBUTE) LIVE at Stonebridge Restaurant(6pm)
- New Milford: The Outcrops LIVE at Housatonic River Brewing(7pm-10pm)
- New Canaan: RETRO EXPRESS LIVE at Gates Restaurants and Bar(8:30pm)
- 📣 Newtown: Barn Babies Goat Cuddles at Aquila's Nest Vineyards(11:30am)
- 📣 Newtown: Tony & The West Siders LIVE at Aquila's Nest Vineyards(2:30pm-5:30pm)
- Newtown: Fall Carnival - Newtown Parks and Rec(2pm-10pm)
- Newtown: One Level down LIVE at Newsylum Brewing Co(3pm-6pm)
- 📣 Newtown: Back to School 80s and 90s DJ Bingo at Aquila's Nest Vineyards(6pm)
- 📣 Newtown: Fine Pastries and Wine Pairing at Aquila's Nest Vineyards(6pm)
- Newtown: Emma Henning LIVE at Perfusion Bar(8pm-11pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- Ridgefield: Free Whenever LIVE at Nod Hill Brewery(5pm)
- Redding: Oktoberfest Kickoff 2025 LIVE at The Redding Roadhouse(6pm-11pm)
- Redding: Bar Car Band LIVE at Milestone(9pm-12am)
- Stamford: Arts & Crafts on Bedford(10am-6:30pm)
- Stamford: Open Play Chess in Latham Park – Stamford(1pm-3pm)
- Stamford: Live Music by Last Hoorah at The Beer Garden (Shippan Landing)(5pm-8pm)
- 📣 Stamford: Comedian Ivan Decker at New York Comedy Club Stamford(7pm-9:30pm)
- 📣 Stamford: Jimmie Allen at The Palace Theater Stamford(8pm)
- Stamford: Mugshot LIVE at Tiernan's(9:30pm)
- Stratford: Round Two LIVE at Outriggers(5:30pm-8:30pm)
- Stratford: Stereobomb LIVE at Windmill Restaurant(8pm)
- Stratford: Bernadettes LIVE at Joey C’s Boathouse(8pm-12am)
- Sherman: MADZ Muzic LIVE at JCC in Sherman(7pm-9pm)
- Westport: PopUp Shop Market Returns to Westport – Saturday, September 20th(10am-3pm)
- Shelton: Da' Band LIVE at Pier131(9:30pm)
- Westport: Art in the Barn! at Westport Country Playhouse(12pm-4pm)
- Westport: The Girls LIVE at Black Duck Cafe(9:30pm)
- Westport: Argonaut & Wasp w/s/g Wild & Co. at Levitt Pavilion(7pm)
- Woodbury: Zac ’n’ Fried LIVE at Woodbury Brewing Company(8:30pm)
- 📣Bridgeport: Beardsley Zoo is now part of the CT Season Pass!(10am)
- Bridgeport: Andy & Scott LIVE at Port 5(3pm)
- Bridgeport: The Red Planet LIVE at BRYAC(6pm)
- Bethel: DIRTY MARTINIS LIVE at Shakedown Street(12pm)
- Bethel: OKTOBERFEST at Broken Symmetry(2pm)
- Bethel: MYSTERY TRAIN LIVE at Notch 8(5pm)
- Bethel: Tom Duffy Band LIVE at Broken Symmetry(6pm)
- 📣Danbury: 2025 Greater Danbury Irish Festival(12pm-6pm)
- Danbury: OAKtoBEERfest(1pm-3pm) at Charter Oak Brewing
- Danbury: Between the Keys LIVE at Charter Oak Brewing(3pm-5pm)
- Derby: Anthony David LIVE at Badsons Beer(2pm-5pm)
- Greenwich: The Annual PUTTIN' ON THE DOG(10am-4:30pm)
- Lebanon: 27th Annual Connecticut Renaissance Faire(10:30am-6pm)
- New Milford: Dan Sawyer LIVE at Housatonic River Brewing(4pm-7pm)
- Newtown: Girl Scout Cookies & Wine Pairing(12pm)
- 📣 Newtown: Sourdough 101 Class at Aquila's Nest Vineyards(12pm)
- 📣 Newtown: The Vanity Project LIVE at Aquila's Nest Vineyards(2pm-5pm)
- 📣 Newtown: Joni Mitchell and Cat Stevens Tribute at Aquila’s Nest Vineyards(6pm-9pm)
- Newtown: Fall Carnival - Newtown Parks and Rec(1pm-5pm)
- Newtown: Bone Dry Live at Reverie Brewing Co(2pm-5pm)
- Newtown: The Oktoberfest Band LIVE at Newsylum Brewing Co(2pm-5pm)
- Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
- 📣 Stamford: Comedian Charles McBee at New York Comedy Club Stamford(7pm)
- Stratford: Kathy Thompson Band LIVE at Two Roads(2pm-4:30pm)
- Stratford: Pimpinella LIVE at Joey C’s Boathouse(3pm-7pm)
- Seymour: Seymour Pumpkin Festival(10am-5pm)
- Shelton: Harvest Fest Live Music at Jones Family Farms(1:30pm-4:30pm)
- Shelton: Billy G and Friends LIVE at Spotted Horse(4pm)
- Westport: Hintz & Carlucci LIVE at Walrus Alley(12pm-1pm)
- Westport: Art in the Barn! at Westport Country Playhouse(12pm-4pm)
- Weston: Chamber Music w/ Harp at Weston Library September 21(4pm-6pm)
- Woodbury: Gender Mutiny LIVE at Woodbury Brewing Company(2pm)
Celebrate 3 years of laughs on March 1 at 4:30 PM with a special matinee showcase featuring top comics, great vibes, and nonstop stand-up fun.
Connecticut folk-rock favorites The Moonrise Cartel bring soaring harmonies and high-energy Americana to Daryl’s House in Pawling, NY on April 9. Get tickets now.
Enjoy a free “Blues & Beyond” concert at First Congregational Church of Stamford in Stamford, exploring African American history through music. Reserve seats now.
Join Team Woofgang & Co. for Bunco Blast on Feb 26—games, drinks, and fun supporting adults with disabilities. First session sold out; limited spots left for the 2nd session!
Experience Drew Angus live at SHU Community Theatre March 21 for a powerful night of timeless rock and storytelling.
Best-selling author Claire Dederer joins Hilarie M. Sheets at Verso Fest'26 - March 28th to discuss Monsters: A Fan’s Dilemma and the ethics of art.