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.

Friday, September 26, 2025 

• 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) 

Saturday, September 27, 2025 

• 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) 

Sunday, September 28, 2025  

• 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)