Autumn has arrived in Fairfield County, bringing with it crisp air, colorful foliage, and a calendar packed with seasonal celebrations. From cozy harvest festivals and spooky Halloween haunts to pumpkin patches , apple orchards, and charming local markets, there’s no shortage of ways to embrace the magic of fall. Whether you’re looking to sip cider under the stars, take the kids on a hayride, get lost in a corn maze, or enjoy a night of live music and local brews, this season’s lineup has something for everyone. So, grab your favorite sweater, gather your family and friends, and explore all the fun, food, and festivities happening in and around Fairfield County this fall . Below, we’ve rounded up some of the area’s can’t-miss events, from weekend fairs to haunted happenings — and everything in between. Wednesday, October 15 📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm) Bethel: Jim Royle's Caribbean Jazz Connection LIVE at La Zingara(7pm) Bethel: Blue Jay Orchards PYO Pumpkins & Wagon Rides(11am-5pm) Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm) Higganum: Pumpkin Patch at Halfinger Farms(9am-6pm) Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm) 📣Newtown: Astrology Reading Night at Aquila's Nest Vineyards(5:30pm) 📣Newtown: Pilates with Goats at Aquila's Nest Vineyards(6pm) 📣Newtown: Sip n Learn French Class at Aquila's Nest Vineyards(6pm) North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm) Pawling, NY: Toronzo Cannon LIVE at the Daryl's House(7pm) 📣Stamford: Comedian Jenny Zigrino at New York Comedy Club Stamford(7pm) Tarrytown, NY: Ghost Tours of The Music Hall 2025 LIVE at Tarrytown Music Hall(8pm) Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm) Wilton: Beauty is Resistance: art as antidote(11m-6pm) Thursday, October 16 📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm) Bethel: Blue Jay Orchards PYO Pumpkins & Wagon Rides(11am-5pm) Bedford, NY: Hudson Valley Wind Quintet LIVE at Bedford Playhouse(7pm) Fairfield: Tangled Vine LIVE at The Sinclair(8:30pm) Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm) Higganum: Pumpkin Patch at Halfinger Farms(9am-6pm) Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm) Milford: Young Dan & Friends LIVE at Cafe Atlantique(5pm-8pm) 📣Newtown: Build Your Own Apple Bar at Aquila's Nest Vineyards(6pm) 📣Newtown: Hocus Pocus Need Wine to Focus Drag Show at Aquila's Nest Vineyards(6:30pm) 📣Newtown: Newtown Speaker Series: Wally Lamb at Edmond Town Hall(7pm-9pm) Norwalk: Live music with STEVEN KEITH!(5:30pm-8:30pm) Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm) Port Chester, NY : An Evening with Patty Griffin + Rickie Lee Jones LIVE at the The Capitol Theatre(8pm) Pawling, NY: Sir Paul: Tribute to Paul McCartney LIVE at the Daryl's House(8pm) Ridgefield: Traditional Irish Session LIVE at Nod Hill Brewery(6pm) Stamford: The Lodge at the Riverbank Ramble - Don Zlotnick & Christine Chanel (6:30-9:30pm) 📣Stamford: Comedian Usama Siddiquee - The Usama Bin Laughin Tour at New York Comedian Club Stamford(7pm) 📣Stamford: Not Dead Yet! - John Cleese and the Holy Grail at 50 at The Palace Stamford(7:30pm) South Windsor: Foster Family Farm Corn Maze(10am-6pm) Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm) Tarrytown, NY: Pink Martini All Stars LIVE at Tarrytown Music Hall(8pm) Westport: Chris Coogan Meets the Jazz Rabbi LIVE at Jazz at the Post(7:30pm-10:30pm) Wilton: Beauty is Resistance: art as antidote(11m-6pm) Friday, October 17 Bridgeport: Elana Zabari LIVE at Port 5(5pm-8:30pm) 📣Bridgeport: North County Band with Sasco Dead - Park City Music Hall - Bridegeport CT(8pm-11pm) Bethel: MICHAEL BRAM LIVE at Shakedown Street(6:30pm) Bethel: Blue Jay Orchards PYO Pumpkins & Wagon Rides(11am-5pm) 📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm) Danbury: Shameless LIVE at Elicit Brewing Danbury(9pm) Danbury: DJ GIODE at the Speak Easy - Elicit Brewing Danbury(10pm) Fairfield: DJ CHARLIE at the Speak Easy - Elicit Brewing Fairfield(10pm) Fairfield: Harvest Fair Halloween Haunt(7pm-10pm) Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm) Hartford: The Name Droppers Perform Live At Black-Eyed Sally's Southern Kitchen And Bar(8am-11pm) Higganum: Pumpkin Patch at Halfinger Farms(9am-6pm) Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm) Milford: Paul Loether LIVE at Cafe Atlantique(6:30pm-9:30pm) Mamaroneck, NY: Naturally 7 LIVE at Emelin Theatre(8pm) New Milford: The Winnie Shins LIVE at Housatonic Brewery(7pm-10pm) New Haven: Ghosts of New Haven(7:30pm) 📣Newtown: Frank Lind LIVE at Aquila's Nest Vineyards(5:30pm-8:30pm) 📣Newtown: Local Cheese & Wine Pairing at Aquila's Nest Vineyards(6pm) 📣 Brie & Vino Nights at Aquila's Nest Vineyards(6:30pm) Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm) Newtown: Sal Grillo LIVE at Perfusion Bar(8pm-11pm) 📣Norwalk: Brother Dave LIVE at SONO 1420(6pm-9pm) Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) Norwalk: Fake ID Band LIVE at 314 Beer Garden(7pm-11pm) North Salem, NY: Mystic Moon at Harvest Moon Farm and Orchards(7pm) North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm) Pawling, NY: The Third Mind LIVE at the Daryl's House(8pm) Ridgefield: Old Bob LIVE at Nod Hill Brewery(6pm) Ridgefield: The Loner ~ The Music of Neil Young LIVE at Nod Hill Brewery(6:30pm) Rowayton: The Third Rail LIVE at Sails American Grill(9:30pm) Rye, NY: Scarded By The Sound at Playland(8pm-11pm) Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm) Stratford: Jon Hollywood LIVE at Windmill Tavern(5pm) Stamford: Whiskey & Woodfire at Stamford Museum & Nature Center(6:30pm) 📣Stamford: Comedian Brittany Brave at New York Comedy Club Stamford(7pm) Stamford: Dive Bar Confessional LIVE at Third Place by Half Full Brewery(7pm-9pm) Stamford: Suck R' Punch LIVE at Bobby V's(7pm-10pm) 📣Stamford: Anthony Rodia: Laugh till It Hurts Tour at The Palace Stamford(8pm) Stamford: Something Fried LIVE at Tiernan's Bar(9:30pm) 📣Stamford: That's Fair Comedy at New York Comedy Club Stamford(9:30pm) Stamford: Club Shebeen at Tigin Irish Pub(10pm) Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm) Tarrytown, NY : Marty Stuart and His Fabulous Superlatives LIVE at Tarrytown Music Hall(8pm) Wethersfield: Cove Side Carnival 2025(5pm-10pm) 📣Westport: StoryFest to Celebrate Storytelling in All Its Forms with Special Film Screening and Concert Event(6:30pm) Westport: Ruff Dogs LIVE at Black Duck Cafe(9:30pm) Saturday,October 18 📣Bridgeport: The Anna & Raven Goodwill Trick or Treat Day at Sacred Heart University's Discovery Science Center and Planetarium(10am) Bridgeport: Oktoberfest 2025 at Foolproof Brewing Co. Bridgeport(12pm-10pm) Bethel: JUSTIN VIRGA LIVE at Shakedown Street(6:30pm) Bethel: Beatnicks LIVE at Notch 8(8pm) 📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm) Bedford, NY: Alison Shearer Album Release Concert and Party LIVE at Bedford Playhouse(8pm) Branford: The Traveling Bazaar at Caius Brewing(11am-5pm) Colchester: Colchester Food Truck and Wine Festival(11am-6pm) Danbury: Tony & The West Siders LIVE at Charter Oak Taproom(4pm-7pm) Danbury: Five Dollar Shake LIVE at Elicit Brewing Danbury(9pm) Danbury: DJ MIKEY LIVE in the Speak Easy at Elicit Brewing Danbury(10pm) Easton: Pumpkin Patch at Silverman's Farm(9am-5pm) East Windsor: Pumpkin Patch at Connecticut Trolley Museum(10am-4pm) Fairfield: Fairfield Harvest Market(10am-4pm) Fairfield: Juicebox LIVE at Elicit Brewing Fairfield(9pm) Fairfield: DJ JAY SPRING LIVE in the Speakeasy at Elicit Brewing Fairfield(10pm) Fairfield: Harvest Fair Halloween Haunt(7pm-10pm) Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm) Goshen: Fall Festival on the Zoo Farm - Action Wildlife Foundation(5pm) Harwinton: All Hallows Weekend at The Connecticut Renaissance Faire(10:30am-6pm) Lebanon: 27th Annual Connecticut Renaissance Faire(10:30am-6pm) Litchfield: Bunnell Farm Corn Maze & Pumpkin Patch(10am-5pm) Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm) Milford: Milford Artisan Market(10am-4pm) Mystic: Mystic Apple Festival(11am-6pm) New Canaan: STRICTLY BUSINESS LIVE at Gates Restaurants & Bar(8:30pm-11:30pm) New Milford: Dan's Garage LIVE at Housatonic Brewery(7pm-10pm) New Milford: Scarrybrooke Park CT's Haunted Trail(6pm) New London: Boo Bash at the Beach 5!!!(11am-4pm) New Haven: Ghosts of New Haven(7:30pm) 📣Newtown: Long River Jam LIVE at Aquila's Nest Vineyards(2:30pm-5:30pm) 📣Newtown: Silent Disco Costumes Party at Aquila's Nest Vineyards(6pm) Newtown: Chris Daly LIVE at Newsylum Brewing(3pm-6pm) Newtown: Night Corn Maze at Castle Hill Farm(5pm-8pm) 📣Newtown: Mike DelGuidice comes to Edmond Town Hall(8pm-10pm) Newtown: DJ D Brown LIVE at Perfusion Bar(8pm-11pm) Newtown: Fall Festival at Castle Hill Farm(10am-5pm) Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) Norwalk: Music of the Sea: Norwalk Concert Hall at Norwalk City Hall(7:30pm-9pm) North Salem, NY: Mystic Moon at Harvest Moon Farm and Orchards(7pm) Old Greenwich: Phunk and Roses LIVE at Bosco's Bar & Grill(9pm-12am) Putnam: Putnam's Great Pumpkin Festival(10am-3pm) Pawling, NY: Jim Pospisil LIVE at the Daryl's House(12pm-2pm) Pawling, NY: WILDSIDE LIVE at the Daryl's House(8pm) Ridgefield: Skylab LIVE at Nod Hill Brewery(3:30pm) Redding: Not My Problem LIVE at Milestone(9pm-12am) Shelton: Juliet’s Run LIVE at Pier 131(9:30pm-12am) Shelton: Legends of Fear(7pm) 📣Stamford: WineFest on Bedford(3pm-5:30pm) 📣Stamford: Comedian Natalie Cuomo at New York Comedy Club Stamford(7pm-9:30pm) Stamford: Slowburn LIVE at Tiernan's Bar(9:30pm) Stamford: Blood-Manor(6pm-10pm) Stratford: Whabendos LIVE at Windmill Tavern(8pm) Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm) Tarrytown, NY: Eric D'Alessandro LIVE at Tarrytown Music Hall(6 & 9pm) Wethersfield: Cove Side Carnival 2025(12pm-10pm) Westport: Beardsley Gala(6pm) Westport: Bad Manners LIVE at Black Duck Cafe(9:30pm) Wilton: Halloween Spooktacular at The Riverbrook Regional YMCA(4pm-7:30pm) Windsor: Pumpkin Patches, Hay Rides and Mazes / Corn at Brown's Harvest(10am-5pm) Sunday, October 19 Bethel: TYE DYE BRUNCH w/ ROB GLASSMAN LIVE at Shakedown Street(12pm) Bethel: Black Rock Blues LIVE at Notch 8(4pm) Colchester: Colchester Food Truck and Wine Festival(11am-6pm) Danbury: Comedian Brad Upton at The Palace Danbury Theatre(2pm) Darien: Orchestra Lumos: Small Space Series- A Tale of Two Prodigies(3pm-4:30pm) Easton: Pumpkin Patch at Silverman's Farm(9am-5pm) East Windsor: Pumpkin Patch at Connecticut Trolley Museum(10am-4pm) Guilford: Making Chocolate the 18th Century Way at Henry Whitfield State Museum(10am-4pm) Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm) Harwinton: All Hallows Weekend at The Connecticut Renaissance Faire(10:30am-6pm) Lebanon: 27th Annual Connecticut Renaissance Faire(10:30am-6pm) Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm) Mystic: Mystic Apple Festival(11am-6pm) Milford: Milford Artisan Market(10am-4pm) Mamaroneck, NY : Fearless – The Taylor Swift Experience LIVE at Emelin Theatre(2pm) New Haven: Ghosts of New Haven(7:30pm) 📣Newtown: Mini Cheesecakes & Sweet Wines Pairing at Aquila's Nest Vineyards(12pm) 📣Newtown: A&R Duo LIVE at Aquila's Nest Vineyards(2pm-5pm) 📣Newtown: Bon Jovi Tribute Show at Aquila's Nest Vineyards(6pm) Newtown: Jailhouse LIVE at Reverie Brewing(3pm-6pm) 📣Newtown: Fine Cigars Night at Aquila's Nest Vineyards(6pm) Norwalk: Blue Skies On Mars LIVE at 314 Beer Garden(3pm-6pm) Norwalk: Jazz Band LIVE at Odeen’s Norwalk(7:15pm) Pawling, NY: Greg Raposo LIVE at the Daryl's House(12pm) Pawling, NY: Night of Nicks: The Stories, The Music of Stevie Nicks & Fleetwood Mac LIVE at the Daryl's House(7pm) 📣Stamford: Air Supply returns The Palace Stamford(7pm) 📣Stamford: Comedian Tom Shillue at New York Comedy Club Stamford(7pm) Vernon: Strong Family Farm Harvest Festival(10am-3pm) Wethersfield: Cove Side Carnival 2025(12pm-6pm) Westport: MoCA\CT Presents: Caity Gyorgy + Band(4pm-6pm) Windsor: Pumpkin Patches, Hay Rides and Mazes / Corn at Brown's Harvest(10am-5pm)

Fall is in full swing at Aquila’s Nest Vineyards , and this week’s lineup is pure magic — from witchy gatherings to dazzling drag shows, silent discos, and even a Bon Jovi tribute to wrap it all up. Grab your friends, your best costume, and your favorite glass of wine because the vineyard is serving up spooky-season vibes all week long! Witchy Wednesdays | October 15 | 6–9 PM The spell has been cast, and Witchy Wednesdays continue through the end of October! Round up your witchy girlfriends, dust off your hats, and head to Aquila’s for a mystical midweek meetup. Sip on enchanting wines while soaking in the moonlit vineyard ambiance — broomsticks optional but highly encouraged. Hocus Pocus Drag Show | Thursday, October 16 | 6:30 PM Get ready for some serious hocus pocus! The Hocus Pocus Drag Show brings glitz, glamour, and a whole lot of Halloween sass to the vineyard. Expect spellbinding performances, laughter, and wine that flows as freely as the fun. Make your reservation here before it disappears! Silent Disco Costume Party | Saturday, October 18 | 6 PM Put on your favorite costume and get ready to dance like nobody’s watching — because at the Silent Disco Costume Party , nobody can hear your moves! Grab a headset, choose your music channel, and dance the night away under the stars. 👉 Check availability here before this one fills up — it’s a fan favorite every year! Sunday Funday | October 19 | Two Ways to Unwind Wrap up the weekend your way with two perfect options: Fine Cigars Night | 6 PM Relax with a glass of wine and a smooth cigar in Aquila’s cozy outdoor spaces. It’s the ultimate chill evening with vineyard views and good company. 👉 Reserve your spot here. 1 Wild Night: A Bon Jovi Tribute | 6 PM Prefer to end your weekend on a high note? Rock out to 1 Wild Night and get your Bon Jovi fix before Monday rolls around. 👉 Check availability here. From mystical midweek vibes to weekend dance parties and live music under the stars, Aquila’s Nest Vineyards is the place to be this October. 🍁 Gather your crew, grab your tickets, and toast to a hauntingly good time!