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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.
🧙 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)
🚂 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)
📣 🎸 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)
📣 🍂🍻 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)
Why do people join cults? What keeps them inside? And—most importantly—what does it take to break free? On Saturday, October 18, 2025 , The Palace Theatre Stamford invites you to step inside one of society’s most fascinating and unsettling mysteries with The Psychology of Cults , a powerful live event hosted by renowned cult interventionist Ashlen Hilliard . This gripping evening pulls back the curtain on the world of cults—past and present. From infamous groups like Jonestown, Heaven’s Gate, and NXIVM to lesser known but equally manipulative organizations, Ashlen unpacks the tactics cults use to recruit, control, and isolate their members. Through chilling case studies, expert analysis, and interactive discussion, audiences will see how psychological manipulation works—and why even the smartest and strongest among us can be vulnerable. But cult influence isn’t confined to the headlines. This live show also shines a light on how coercion and abuse can creep into everyday life —within personal relationships, workplaces, wellness movements, and social communities. With real-world stories and insights, Ashlen gives audiences the tools to: Recognize red flags of high-control groups and relationships Understand the psychology that makes people susceptible to manipulation Learn how to protect themselves and others from coercive influence Whether you’re captivated by true crime, intrigued by human behavior, or simply want to understand how to safeguard yourself and your loved ones, The Psychology of Cults offers a thought-provoking, unforgettable night at the theater. Don’t miss this rare opportunity to explore the hidden world of control, coercion, and freedom with one of the leading voices in the field. 📍 The Palace Theatre Stamford 📅 Saturday, October 18, 2025 🎟 Tickets start at $25 ⏰ Doors 7 PM | Show 8 PM 👉 Secure your seats now and take the first step in understanding the powerful psychology behind cults.
Thursday, October 9 | 7 PM Aquila’s Nest Vineyards The vineyard comes alive on October 9 with music, community, and a powerful cause! Mombies DJ Night: Raising Spirits & Funds takes place on Thursday, October 9 at 7 PM —and it’s sure to be an evening to remember. Enjoy an evening of great music as DJ RJ Borruso spins your favorite hits under the autumn sky. Throughout the night, guests will also meet the inspiring Fairfield MOMbies (mombies.org)—a group of local moms who transform into zombies each October to raise awareness and funds for metastatic breast cancer research . Since their founding, the MOMbies have raised nearly $700,000 to support groundbreaking research and improve outcomes for those living with metastatic breast cancer. Their energy, creativity, and passion have made them a beloved part of the community—and now they’re bringing their mission to the vineyard. This outdoor fundraiser will be hosted in Aquila’s cozy Fire Pit Circles , where guests can sip wine, warm up by the fire, and soak in the vineyard’s magical fall atmosphere. Keep an eye out for MOMbies wandering the grounds—they’ll be joining in for photo ops, wine tastings, and spooky fun, while sharing their mission and stories of impact. All ticket sales will be donated to MOMbies.org , directly supporting metastatic breast cancer research and providing hope to families impacted by the disease. Please note: this is a Halloween meet-and-greet , not a MOMbies dance performance. Event Details 📍 Aquila’s Nest Vineyards 📅 Thursday, October 9, 2025 ⏰ 7:00 PM 🎟️ Tickets required for all guests ages 3+ Raise a glass, raise your spirits, and help raise funds for an extraordinary cause. Together, we can make a difference—one song, one laugh, and one toast at a time. Join the MOMbies at the Vineyard!
The Friday Night Acoustic SONO Fall Music Series at SONO 1420 America’s Maritime Distillery continues this October with great music, craft spirits, and now an incredible new food experience!
Acclaimed author Wally Lamb comes to Edmond Town Hall on Thursday, October 16 , for a special evening of conversation and storytelling. Called “a modern-day Dostoyevsky [who] never grapples with anything less than life’s biggest questions” by The New York Times Book Review , Lamb is the author of six New York Times bestsellers and a rare three-time Oprah’s Book Club pick . His novels include She’s Come Undone , I Know This Much Is True (adapted into an Emmy-winning HBO series starring Mark Ruffalo), The Hour I First Believed , We Are Water , Wishin’ and Hopin’ , and I’ll Take You There . His latest novel, The River is Waiting , continues his tradition of profound, character-driven storytelling. In addition to his fiction, Lamb has edited anthologies featuring the voices of women incarcerated at Connecticut’s York Correctional Institute, work that earned national recognition and a feature on 60 Minutes . A Connecticut native, teacher, and literary voice of compassion and humanity, Wally Lamb offers readers stories of imperfect people striving to grow and connect. Don’t miss this opportunity to hear from one of America’s most celebrated writers. Tickets available at EdmondTownHall.org
The 3rd Newtown Record Riot takes place on Sunday, October 5, 2025, at 10 AM $5 entry fee (Early Birds 9:00 AM, $10 entry fee) until 4:30 PM in the Edmond Town Hall gym, 45 Main Street in Newtown, CT 06470. Beach Boys co-founder Brian Wilson shared with the Los Angeles Times that “Vinyl has a warmth to it, a soul. Digital doesn’t really capture that emotion. When I first heard my music on vinyl, it was like hearing it in full color, and that’s how I still feel about it.” Come shop at over 30 tables of LPs, CDs, 45s and more. Dealers from all over New England and beyond. Meet new music friends, find that special LP that you've been looking for. All types of music: punk, funk, country, classical, blues rock, hip hop and more. $5.00 regular admission starts at 10 AM, with early admission kicking off at 9 AM ($10). Nomad Bites food truck will be on site selling breakfast sandwiches and lunch food throughout the day. Beer from local breweries NewSylum and Watson Farmhouse Brewery available for purchase. Free Parking, entrance to gym in back of the building. Portions of the event will support Friends of Edmond Town Hall (FOETH), whose mission statement is ‘Committed to bringing arts and humanities programming and events to the community at large while maintaining the historic Edmond Town Hall. For more information about Record Riots visit www.recordriots.com. For more information or how to join, donate, volunteer or sponsor Friends of Edmond Town Hall please visit www.FriendsofETH.org or email friendsofeth@gmail.com.
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)