Pumpkins, Apples & Halloween Haunts: Top Things to Do This Week in and around Fairfield County.

Fall Adventures in and Around Fairfield County, CT   

When the crisp air rolls in and the leaves turn to shades of gold and crimson, Fairfield County, CT, comes alive with fall magic. From pumpkin patches and apple orchards to haunted happenings and cozy wine tastings, there’s something for everyone to enjoy this season. Here are some of the best fall adventures to experience in and around Fairfield County. 

October 1, 2025 (Wednesday) 

🧙 CT Witch Crawl Kickoff — The statewide metaphysical / “witchy” shops crawl begins across CT, including stops in Fairfield County. Collect stamps, explore local spiritual shops, and enter raffles.  

🕯📣 ️ Witchy Wednesdays at Aquila’s Nest Vineyards   – Every Wednesday in October 

📣 😂🥊   Roast Battle at New York Comedy Club Stamford   - Watch comics go head-to-head with no mercy 

•  Bethel: Vocalist Giacomo Gates Trio Feat. Phil Bowler & Tony Lombardozzi at La Zingara(7pm) 
• Cos Cob: Mike Milazzo LIVE at Cos Cobbler(4pm-6pm) 
• East Haven: Bluegrass Jam at the Museum(6pm-8:30pm) 
• 📣 Newtown: Salsa & Bachata Dance Night at Aquila's Nest Vineyards(6pm) 
• 📣 Newtown: Sunset Zumba in the Vineyard at Aquila's Nest Vineyards(6pm) 
• 📣 Newtown: Yoga in the Vineyard at Aquila's Nest Vineyards(6pm) 
• Ridgefield: Al Rivoli LIVE at 850 Degrees(5pm) 

October 2, 2025 (Thursday) 

🚂 Tracks of Terror — Essex Steam Train — This immersive haunted train experience runs on Thursdays (plus Fridays & Saturdays) through October.  

🪕 Bluegrass Nights at The Granite Church ( 7:00pm – 10:00pm) 

🍻 Fall / Oktoberfest Evening in a Local Town — Many towns host Oktoberfest or harvest-themed evenings with beer, food, and live music.  

•  Bethel: DJ DIZZASTER LIVE at Notch 8(8pm) 
• Danbury: Line Dancing every Thursday night at Elicit Brewing Danbury(7pm) 
• Danbury: Sweet & Low LIVE at Sugar Hollow(8pm) 
• Fairfield: Car Cruises at Elicit Fairfield(5pm) 
• Fairfield: Salsa Nights at Elicit Fairfield(8pm) 
• Fairfield: ETA MUSIC LIVE at The Sinclair(8:30pm) 
• Milford: Ode To Rosie LIVE at Cafe Atlantique(6:30pm-9:30pm) 
• 📣 Newtown: Llamas and Llibations at Aquila's Nest Vineyards(6:30pm) 
• 📣 Newtown: Dave Vargo LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm) 
• 📣 Newtown: Wine, Words & Wisdom Book Club Series at Aquila's Nest Vineyards(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) 
• 📣 Stamford: Comedian Juston McKinney at New York Comedy Club Stamford(7pm) 
• Stratford: Eric Christensen LIVE at Blackbird's Nest(5pm-8pm) 
• Woodbury: The Dave Matthews Tribute Band LIVE at Woodbury Brewing Company(6:30pm)  
• Westport: Melissa Newman LIVE at Jazz at the Post(7:30pm) 
• Westport: Live music with Billy Genuario(9pm) 

October 3, 2025 (Friday) 

📣 🎸 Vennie Ferrone at SONO 1420 America’s Maritime Distillery (6:00 – 9:00pm) 

📣 🎹 Bennie & The Jets at Edmond Town Hall (8:00-10:00 pm) 

Experience the magic of Elton John with this premier tribute band 

👽 ALIEN INVASION: Haunted Trolley Ride — The Shore Line Trolley Museum hosts this special Halloween-themed ride event on October 3 & 4.  

•  Bethel: MIKE & IKE LIVE at Dragonfly(6pm-9pm) 
• Bethel: MYSTERY TRAIN LIVE at Notch 8(8pm) 
• Bethel: JOHNNY CHAPMAN LIVE at Shakedown Street(6:30pm) 
• Bridgeport: Ethyl Flying Solo LIVE at Port 5(5pm-8:30pm) 
• Danbury: Jordan Toma is "Just a Kid With an IEP" at The Palace Danbury Theatre(7pm) 
• Danbury: North County Band at Sugar Hollow(7pm) 
• Danbury: “Thy Will Be Done” Interactive Theater at Wilton Historical Society(7pm-8:30pm) 
• Danbury: Jeff Petescia Live at Charter Oak Brewing(7pm-9pm) 
• Danbury: “Thy Will Be Done” Interactive Theater Performance(8pm-9:30pm) 
• Danbury: Sex & Candy LIVE at Elicit Brewing Danbury(9pm) 
• Danbury: DJ ROC at Elicity Brewing Danbury(10pm) 
• Fairfield: Diva & The Play Boys LIVE at Elicit Fairfield(9pm) 
• Fairfield: DJ DONNY D in the Speakeasy at Elicit Fairfield(10pm) 
• Greenwich: Greenwich Library Opening Night Celebration with Music From The Sole(7pm-10pm) 
• 📣 Harwinton: 168th Annual Harwinton Fair(4pm-9:30pm) 
• Milford: Mat Kastner & Friends LIVE at Cafe Atlantique(6:30pm) 
• New Milford: Five to One LIVE at Housatonic River Brewing Co.(7pm) 
• 📣 Newtown: Dylan Connor LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm) 
• 📣 Newtown: Fall Belgian Chocolate and Wine Pairing at Aquila's Nest Vineyards(6pm) 
• 📣 Newtown: Wine and Wheels Car Show at Aquila's Nest Vineyards(6pm) 
• 📣 Newtown: Yappy Hour - Bring Your Furry Friends at Aquila's Nest Vineyards(6pm) 
• 📣 Newtown: Albanian Traditions Harvest Celebration at Aquila's Nest Vineyards(6:30pm) 
• Newtown: Jake Kulak LIVE at Reverie Brewing(6pm-9pm) 
• Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm)  
• 📣 Newtown: Bennie & The Jets at Edmond Town Hall(8pm) 
• Newtown: Shay Sullivan LIVE at Perfusion Bar(8pm-11pm) 
• 📣 Norwalk: Vinnie Ferrone LIVE at SONO 1420(6pm-9pm) 
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) 
• Norwalk: Thin Sandwich Band at O'Deens – Norwalk(7pm) 
• Norwalk: Pimpinella LIVE at 314 Beer Garden(7:30pm-11pm) 
• 📣 Portland: 25th Annual Portland Fair(3pm-11pm) 
• Rowayton: Ron Wilson Band LIVE at Sails(9:30pm) 
• Redding: Mike Milazzo LIVE at the Redding Roadhouse(7pm-10pm) 
• Ridgefield: Gab Kallay at O'Deens – Ridgefield(6pm) 
• Ridgefield: The Hot Club of Black Rock LIVE at Nod Hill Brewery(6:30pm) 
• Stamford: Club Shebeen at Tigin Irish Pub(10pm) 
• Stamford: Just Below Me Live at Tiernan's(9:30pm) 
• Stamford: Retro Express LIVE at Third Place(7pm-9pm) 
• 📣 Stamford: Comedian David Nihill at New York Comedy Club Stamford(7pm-9:30pm) 
• Stamford: CORE LIVE at Bobby V's(7pm-9pm) 
• 📣 Stamford: HOW?! The Magic Show at The Palace Stamford(7:30pm) 
• Stratford: Night Visitors duo LIVE at the Windmill Tavern(5pm) 
• Stratford: Chris Q LIVE at Blackbird's Nest(6pm) 
• Stratford: DKP BAND LIVE at the Windmill Tavern(8pm) 
• Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm) 
• Sherman: Poetry Showcase: Season Of The Witch at JCC in Sherman(7pm-9pm) 
• Westport: Hitch & the Giddyup LIVE at Walley Alley(7:30pm) 
• Westport: Bar Car Band LIVE at Black Duck Cafe(9:30pm) 
• Woodbury: STREETS - The Ultimate Tribute to 80's Hair Metal at the Woodbury Brewing Company(8:30pm) 

 October 4, 2025 (Saturday) 

📣 🍂🍻 WestoberFest (12pm-6pm) — Craft Beer & Family Fall Festival in Downtown Westport  

🍺🥨 OKTOBERFEST kickoff at Elicit Brewing Danbury 

📣 🩸 Blood – Manor Kicks off at Stamford Town Center —  

“Step inside Stamford’s scariest haunted house experience   

•  Bridgeport:Greater Bridgeport Symphony (GBS) Kicks Off 80th Season With “Horizons of The Air” October 4 at The Klein Memorial Auditorium in Bridgeport, CT 
• Bethel: ERIK RABASCA LIVE at Shakedown Street(6:30pm) 
• Bethel: ROB GLASSMAN BAND LIVE at Notch 8(8pm) 
• Danbury: OKTOBERFEST KICKOFF at Elicit Brewing Danbury(12pm) 
• Danbury: Colonial Tavern Night at Wilton Historical Society(6pm-8pm) 
• Danbury: Peter and His Band of Wolves Live + Dad’s Grill Live at Charter Oak Brewing(7pm-9pm) 
• Danbury: Sister Funk LIVE at Sugar Hollow(8:30pm) 
• Danbury: JUNK LIVE at Elicit Brewing Danbury(9pm) 
• Danbury: DJ FRANKIE at Elicit Brewing Danbury(10pm) 
• Danbury: HiJACKED LIVE at Molly Darcy's(10pm) 
• Danbury: SUCK R PUNCH LIVE at Molly Darcy's(10pm) 
• Darien: OKTOBERFEST 2025 at The Gardener's Center(6pm-10pm) 
• Fairfield: 100 Proof LIVE at Elicit Fairfield(9pm) 
• Fairfield: DJ GIODE in the Speakeasy at Elicit Fairfield(10pm) 
• Hartford: Head of the Riverfront(8am) 
• 📣 Harwinton: 168th Annual Harwinton Fair(9am-9:30pm) 
• Lebanon: 27th Annual Connecticut Renaissance Faire(10:30am-6pm) 
• 📣 Milford: Porchfest – Milford(12pm-6pm) 
• Milford: JAM CHOWDER LIVE at Stonebridge(6:30pm) 
• Mystic: Foodways and Fisheries at the Mystic Seaport Museum(10am) 
• New Milford: Pimpinella LIVE at Housatonic River Brewing(7pm) 
• New Canaan: FAKE ID LIVE at Gates Restaurant & Bar(8:30pm-11:30pm) 
• 📣 Newtown: Fall Desserts & Wine Pairing at Aquila's Nest Vineyards(12pm) 
• 📣 Newtown: The Adults Band LIVE at Aquila's Nest Vineyards(2pm-5pm) 
• 📣 Newtown: Hocus Pocus Need Wine to Focus Drag Show at Aquila's Nest Vineyards(7pm) 
• 📣 Newtown: Buckets N Boards at Edmond Town Hall(3pm-5pm) 
• Newtown: Symphonic Bodega LIVE at Newsylum Brewing(3pm-6pm) 
• Newtown: Sound Dog LIVE at Perfusion Bar(8pm-11pm) 
• 📣 Norwalk: Fall Festival at Rowayton Civic Assoc.(12pm-4pm) 
• Norwalk: RCA Fall Festival 2025(12pm-4pm) 
• 📣 Norwalk: 9th Annual NICE Fest!(12pm-8pm) 
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) 
• Norwalk: Incidental Contact LIVE at 314 Beer Garden(7:30pm-11pm) 
• Old Greenwich: Rock Paper Soul LIVE at Bosco's Bar&Grill(9pm-12am) 
• 📣 Pound Ridge, NY: Pound Ridge Harvest Festival(1pm-6pm) 
• Portland: 25th Annual Portland Fair(10:30am-10pm) 
• Redding: VINTAGE BAND LIVE at Milestone(9pm) 
• Ridgefield: The Oktoberfest Band LIVE at Nod Hill Brewery(1pm) 
• Ridgefield: The Last Minutemen LIVE at Nod Hill Brewery(5pm) 
• Stratford: Max Collins LIVE at Blackbird's Nest(6pm-9pm) 
• Stratford: American 27's LIVE at Windmill Tavern(8pm) 
• 📣 Stamford: New York Comedy Club Stamford Beginner Workshop at New York Comedy Club Stamford(12pm) 
• 📣 Stamford: Comedian David Nihill at New York Comedy Club Stamford(7pm-9:30pm) 
• Stamford: Oktoberfest Weekend– Steinholding & Hammerschlagen competitions & “Rocktoberfest” by the Kovac Brothers at Third Place by Half Full Brewery(2pm-5pm) 
• Stamford: Orchestra Lumos: Wynton and All That Jazz(7:30pm-10pm) 
• 📣 Stamford: Blood-Manor(6pm) 
• Stamford: Big Chief & the Midnight Groove LIVE at Tiernan's(9:30pm) 
• Stratford: COOKED UP LIVE at Two Roads Brewing Co(4pm-6pm) 
• Sherman: Mallas & Coombe - Live at JCC Sherman(7pm-9pm) 
• Shelton: Legends of Fear(7pm) 
• Westport: Vibe Cartel w Scott Chamberland special guest(6:30pm) 
• Westport: Matt Rhone at Walrus Alley(7:30pm) 
• Westport: Caravan of Thieves at Voices Cafe(8pm-11pm) 
• Westport: Sucker Punch LIVE at Black Duck Cafe(9:30pm) 
• 📣 Wilton: Floating Pumpkin Patch at the Riverbrook YMCA(12pm-5pm) 
• Watertown: Watertown Fall Festival(10am) 
• Wethersfield: 43rd Annual Old Wethersfield Arts and Crafts Fair(10am-4pm) 
• Woodbury: Back in Black: AC/DC Tribute at the Woodbury Brewing Company(8:30pm) 

October 5, 2025 (Sunday) 

🎃🍁   PumpkinTown USA -   Step into Pumpkintown U.S.A. for whimsical pumpkin villages, hayrides, and fall family fun! 

🍂 Southington Apple Harvest Festival   — The three-day festival runs Oct 3–5 on Southington Town Green, featuring crafts, food, apple-based treats, family fun.  

🎃🚜 Blue Jay Orchards PYO Pumkins & Wagon Rides (10am-5pm) 

•  Bethel: DRAG BRUNCH LIVE at Shakedown Street(11am) 
• Bethel: GUMBO LIVE at Notch 8(4pm) 
• Bloomfield: Fall Festival at Auerfarm(11am-4pm) 
• Bridgeport: Purvis LIVE at Port 5(3pm) 
• 📣 Danbury: Manhattan Short Film Festival at The Palace Danbury Theatre(3pm) 
• Danbury: Between the Keys LIVE at Charter Oak Brewing(3pm-5pm) 
• 📣 Harwinton: 168th Annual Harwinton Fair(9am-6pm) 
• Hunter, NY: OKTOBERFEST at Hunter Mountain(11am-6pm) 
• Lebanon:27th Annual Connecticut Renaissance Faire(10:30am-6pm) 
• 📣 Newtown: Grape Harvest Volunteer Registration at Aquila's Nest Vineyards(8am) 
• 📣 Newtown: One Track Mind LIVE at Newsylum Brewing(2pm-5pm) 
• Newtown: RAE LIVE at Reverie Brewing(2pm-5pm) 
• 📣 Newtown: Rockoustic Duo LIVE at Aquila's Nest Vineyards(2:30pm-5:30pm) 
• 📣 Newtown: Meat Loaf Tribute Show at Aquila’s Nest Vineyards(6pm-9pm) 
• Norwalk: Incidental Contact LIVE at 314 Beer Garden(3pm-6pm) 
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) 
• Portland: 25th Annual Portland Fair(10:30am-6pm) 
• Redding: OCTOBERFEST at Milestone(3pm-8pm) 
• 📣 Stamford: New York Comedy Club Stamford Beginner Workshop at New York Comedy Club Stamford(12pm) 
• Stratford: Gab Kallay LIVE at Blackbird's Nest(12pm-3pm) 
• Shelton: Sketchy at Best Band LIVE at Spotted Horse(4pm) 
• Stratford: TIMMY MAIA LIVE at Two Roads Brewing Co(2pm-4:30pm) 
• Westport: Hot Club of Black Rock LIVE at Walrus Alley(12pm)