99+ Things to Do This Halloween Weekend in Fairfield County

It’s the   final   weekend of Halloween happenings, Fairfield County — and the spirits are calling!  👻

Whether you’re chasing chills at haunted houses and ghost tours, shaking your bones at costume parties and bar crawls, or enjoying a little pumpkin-spiced family fun, there’s something for every ghost, ghoul, and goblin in your crew. And if you’ve already checked off all your Halloween plans and just want to kick back, we’ve got you covered with our daily local live music schedule — the perfect soundtrack to relax and unwind.

Want to go incognito for a night? Check out our Halloween Events List for masquerades and monster bashes. Still owe the kiddos that pumpkin-picking promise? Our Fall Festival & Pumpkin Patch Guide is your shortcut to fall perfection. And if your idea of fun involves a few heart-pounding screams, head straight to our Haunted Happenings Page — enter if you dare. 🕸️

So grab your costume, round up your ghoul gang, and creep it real — this is your last chance to make Halloween 2025 one for the (tomb)books! 💀🎃

Wednesday, October 29th

• Bethel: Johnson, Zurkowski, Feeney & Post LIVE at La Zingara(7pm)
• 🎃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)
• Fairfield: Mixtape Match at Elicit Brewing Fairfield(7pm)
• 🌽🎃🚜 📣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: Tarot Reading with Jenny Gypsy at Aquila's Nest Vineyards(5:30pm)
• 📣Newtown: On the Road Again LIVE at Aquila's Nest Vineyards(6pm-9pm)
• 📣Newtown: Witchy Wednesdays at Aquila's Nest Vineyards(6pm-9pm)
• 📣New Canaan: New Canaan Chamber Music Presents: Carnegie Hall to New Canaan(7pm-9pm) 
• 🎃🌽📣North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm)
• Port Chester, NY: Cage The Elephant with hey, nothing and Common People LIVE at the The Capitol Theatre(6:45pm)
• Pawling, NY: GA-20 and Black Joe Lewis & The Honeybears LIVE at Daryls House(7pm)
• 🤣📣Stamford: Comedian Nataly Aukar at New York Comedy Club Stamford(7pm)
• 🎃Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm)
• 🕷️🥁🌕📣Westport: Halloween Parade on Main Street, Westport(3:30pm)

Thursday, October 30th

• 🎃🚜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)
• Bridgeport: Hurley Hour LIVE at BRYAC(6pm)
• Bridgeport: Jimmy Ero LIVE at The Castle Black Rock(7pm-10pm)
• Bridgeport: Party with Friends LIVE at BRYAC(9pm) 
• Danbury: Line Dancing every Thursday night at Elicit Brewing Danbury(7pm)
• Danbury: Thursday Open Jam w/ Sweet & Low LIVE at Sugar Hallow Taproom(8pm-11pm)
• 🕸️👻Danbury: HALLOWEEN EVE at Molly Darcy's(10pm)
• 🕸️👻📣Fairfield: THILLER THIRSDAY - A benefit concert for CLASP featuring Band Central(6:30pm)
• Fairfield: Spellbound Duo LIVE at Elicit Brewing-Fairfield(7pm-10pm)
• Fairfield: Suck’r Punch 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)
• 📣Newtown: Country Line Dancing at Aquila's Nest Vineyards(6pm) 
• 📣Newtown: Whiskers & Wine Kitten Adoption Event at Aquila's Nest Vineyards(6pm)
• 📣Newtown: Dark Sky Telescopes & Stargazing Party at Aquila's Nest Vineyards(6:30pm) 
• Newtown:Junk LIVE at Reverie Brewing(6pm-9pm)
• 🕸️👻Newtown: Halloween Party With Junk LIVE at Reverie Brewing(7pm-9pm)
• 🌽🎃🚜Newtown: Night Corn Maze at Castle Hill Farm(5pm-8pm)
• Norwalk: Live music with STEVEN KEITH!(5:30pm-8:30pm)
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
• 🕸️👻Norwalk: Scare-Aoke Karaoke w/ DJ Marv – 314 Fear Garden(7pm-10pm)
• 🎃🌽North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm)
• Port Chester, NY: Chicago LIVE at the The Capitol Theatre(8pm)
• Pawling, NY: Schools Out: Tribute to Alice Cooper at Daryl's House(8pm)
• Rowayton: DEAN SCALA LIVE at Sails American Grill(6pm-9pm)
• 🤣📣Stamford: Comedian Mike Cannon at New York Comedy Club Stamford(7pm)
• 📣Stamford: Warren Miller's Sno-cietyat The Palace Theatre Stamford(7pm)
• 👻Tarrytown, NY: Ghost Tours of The Music Hall 2025 LIVE at Tarrytown Music Hall(10am)
• 🎃🌽Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm)
• Westport: Brian Marsella LIVE at Jazz at the Post(7:30pm-10pm) 

Friday, October 31st

• 🎭 🕸️👻Bethel: Halloween with Bongo Joe at Shakedown Street Eats(6:30pm-9pm)
• Bethel: Scratch LIVE at Notch 8(8pm)
• 🚜🎃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) 
• 🎭 🕸️👻Bridgeport: Scary-oke LIVE at The Castle Black Rock(8pm-11pm)
• 🎭 🕸️👻Bridgeport: Wiley Griffin Halloween Party LIVE at BRYAC(10pm)
• Cos Cob: Cooked Up LIVE at St. Lawrence Society(7pm-10pm)
• 🎭 🕸️👻Danbury: Halloween Toga Party + Costume Contest + Live music LIVE at Charter Oak Brewing(6pm)
• Danbury: Not Sorry LIVE at Sugar Hallow Taproom(8pm-11pm)
• 🎭 🕸️👻Danbury: Probable Cause - LIVE on Halloween Night at Elicit Brewing-Danbury(9pm)
• 🎭 🕸️👻Danbury: Halloween Night Party at Molly Darcy's(10:30pm-2am)
• Fairfield: Hijacked LIVE at Elicit Brewing-Fairfield(9pm)
• Fairfield: DJ Charlie LIVE at Elicit Brewing Fairfield(10pm)
• Fairfield: DJ GOLDEN BOY LIVE at Elicit Brewing Fairfield(10pm)
• 🕸️👻🎃Fairfield: Harvest Fair Halloween Haunt(7pm-10pm)
• 🌽🚜🎃📣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: Nosmo Kings LIVE at Cafe Atlantique(6:30pm-9:30pm)
• 🎭 🕸️👻Milford: Halloween Party LIVE at Dockside Brewery(9pm)
• 🎭 🕸️👻New Milford: 8th Annual HRB Halloween Party! With Special Guests - Not My Problem LIVE at Housatonic Brewery(7pm-10pm)
• 🎃North Salem, NY: Mystic Moon at Harvest Moon Farm and Orchards(7pm)
• 🌽🎃North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm)
• 👻New Haven: Ghosts of New Haven(7:30pm)
• 🎭 🍷🐾🐕📣Newtown: Howl-o-ween Yappy Hour at Aquila's Nest Vineyards(6pm)
• 🎭 🕸️👻📣Newtown: Halloween Haunted House Costume Party at Aquila's Nest Vineyards(6:30pm)
• 🎭 🕸️👻Newtown: Almost Ablaze Halloween LIVE at Reverie Brewing(6pm-9pm)
• 📣Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm) 
• Newtown: DJ JR In The Mix LIVE at Perfusion Bar(8pm-11pm)
• Norwalk: Electric Fear Garden by E203 at 314 Beer Garden(4pm-11pm)
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
• Norwalk: Green Eyed Lady LIVE at Odeen’s Norwalk(7pm)
• 🎭 🕸️👻Norwalk: Halloween Costume Party & Membership Drive at Pastime(8:30pm)
• 🎭 🕸️👻Old Greenwich: Chasing Romeo’s Halloween Bash LIVE at Bosco's Bar & Grill(9pm-12am)
• Pawling, NY: Brown Sugar - Rolling Stones Tribute at Daryl's House(8pm)
• 🕸️👻Port Chester, NY: Grateful Shred All Hallow's Eve LIVE at the The Capitol Theatre(8pm)
• 🎭 🕸️👻🎃Ridgefield: Halloween Storytime & Parade at Ridgefield Library(10:30am-11am)
• 🕸️👻🎃Ridgefield: Halloween on the Terrace at the First Congregational Church-Ridgefield(5pm-8pm)
• 🎃🚗🍬Ridgefield: Trunk-or-Treat with Ridgefield Police Department at Lounsbury House, Ridgefield(5pm-8:30pm)
• 🎭 🕸️👻Redding: Halloween Party with Louder Daddy - Costume Contest to win $100 Milestone Gift Card!(9pm)
• Rowayton: The Outsyders LIVE at Sails American Grill(9:30pm)
• 🕸️👻Rye, NY: Scarded By The Sound at Playland(8pm-11pm)
• 🎭 🕸️👻Stratford: Halloween Happy Hour LIVE at Two Roads Brewery(4pm-7pm) 
• Stratford: Tempest Edge LIVE at Windmill Tavern(8pm)
• 🤣📣Stamford: Comedian Leslie Liao at New York Comedy Club Stamford(7pm-9:30pm)
• 🎭 🕸️👻Stamford: Half Full Brewery 13th Anniversary Halloween Party LIVE at Third Place by Half Full Brewery(8pm-12am)
• Stamford: Dive Bar Confessional LIVE at Tiernan's Bar(9:30pm)
• 🌽Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm)
• 🎭 Woodbury: 🕸️👻80's Halloween Party with the Pop Rocks at the Woodbury Brewing Company(8:30pm)
• 🎭 🕸️👻Westport: Halloween Dance Party at Basso(7pm)
• Westport: The Girls LIVE at Black Duck Cafe(9:30pm) 

Saturday, November 1st

• Bethel: CHRIS CAVALIERE LIVE at Shakedown Street Eats(6:30pm)
• Bethel: HARMONIC AGGRESSION LIVE at Notch8 Bar(8pm)
• 🎃📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm)
• 🧶🎃🍂Brookfield: Brookfield Festival of Crafts(9am-3pm)
• Bridgeport: ZZ Not LIVE at BRYAC(10pm)
• Danbury: Tony & The West Siders LIVE at Charter Oak Brewing(4pm-7pm)
• Danbury: British Rock Show at Sugar Hollow(8:30pm)
• Danbury: Vibe Atlantic LIVE at Elicit Brewing-Danbury(9pm) 
• Danbury: DJ Evan LIVE at Elicit Brewing-Danbury(10pm)
• Danbury: PROPER VILLIANS LIVE at Molly Darcy's Irish Pub & Restaurant(10pm)
• East Haven: Bluegrass Jam at the Museum(6pm-8:30pm) 
• 🎃Easton: Pumpkin Patch at Silverman's Farm(9am-5pm)
• Fairfield: Kelsey Waldon – Every Ghost Tour LIVE at StageOne FTC(8pm)
• Fairfield: Hawkins French LIVE at Elicit Brewing-Fairfield(9pm)
• Fairfield: DJ MIKEY LIVE at Elicit Brewing-Fairfield(10pm)
• 🎭 🕸️🕷️Fairfield: Harvest Fair Halloween Haunt(7pm-10pm)
• 🌽🎃🚜Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm)
• 🏡🖼️🪑 Hartford: Hartford Fall Home Show(11am)
• 🎃Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm)
• Milford: Inner Groove LIVE at Cafe Atlantique(6:30pm-9:30pm)
• Milford: CHRIS KILEY LIVE at Stonebridge Restaurant(7pm)
• Mamaroneck, NY: Crystal Ship: The Doors Experience LIVE at Emelin Theatre(8pm)
• New Milford:Fortunate Sons LIVE at Housatonic River Brewing(7pm-10pm) 
• 👻New Haven: Ghosts of New Haven(7:30pm)
• New Canaan: FOR LEGAL REASONS LIVE at Gates Restaurant & Bar(8:30pm-11:30pm)
• 🎃North Salem, NY: Mystic Moon at Harvest Moon Farm and Orchards(7pm)
• 🎭 🎃🐾🐶Newtown: Dog Day Halloween Costume Contest at Castle Hill Farm(9:30am-2:30pm)
• 📣Newtown: Chocolate Fondue Dip & Sip at Aquila's Nest Vineyards(12pm)
• 📣Newtown: Halloween Chocolate and Wine Pairing at Aquila's Nest Vineyards(12pm) 
• 📣Newtown: Sip & Shimmy Belly Dancing at Aquila's Nest Vineyards(12pm)
• 🕸️👻📣Newtown: Grapeyard Scavenger Hunt Glow Night at Aquila's Nest Vineyards(5:30pm)
• 🎭 🕸️👻📣Newtown: Midnight Masquerade Murder Mystery at Aquila's Nest Vineyards(6pm)
• 📣Newtown: Stella Blues Band at Edmond Town Hall(8pm)
• Newtown: Tom Ardise LIVE at Perfusion(8pm-11pm)
• 🎨🍂🧶Newtown: Fall Festival at Castle Hill Farm(10am-5pm)
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
• Norwalk: Rowayton Tellabration(7pm-9pm) 
• Norwalk:Sonic Bullet LIVE at 314 Beer Garden(7:30pm-10:30pm) 
• 🎨🍂🧶Oxford: Oxford Arts and Crafts Fair(10am)
• Port Chester, NY: Lawrence - The Family Business Tour with Jacob Jeffries LIVE at The Capitol Theatre(8pm)
• Port Chester, NY: The Rock and Roll Playhouse Plays Music of Taylor Swift + More For Kids LIVE at Garcia's at The Capitol Theatre(12pm)
• Port Chester,NY:  Lawrence Afterparty Jonathan StrÆnge LIVE at Garcia's at The Capitol Theatre(10:45pm)
• Pawling,NY: Wires & Wood LIVE at Daryl's House(12pm)
• Pawling,NY: Facelift: Alice In Chains Tribute LIVE at Daryl's House(8pm)
• Redding: Fuzz & Friends LIVE at Milestone(9pm-12am)
• 🎭 🕸️👻Ridgefield: Nathaniel Hintz's Halloween Revue LIVE at Nod Hill Brewery(6:30pm)
• 🎨🍂🧶Shelton: Shelton Autumn Craft Festival(10am-4pm)
• 🕸️🕷️Shelton: Legends of Fear(7pm) 
• Stratford: BadBoy LIVE at Joey C's Boathouse(9pm-12am)
• 🤣📣Stamford: Comedian Leslie Liao at New York Comedy Club Stamford(7pm-9:30pm)
• Stamford: New Panic LIVE at Tiernan's Bar(9:30pm)
• Stamford: Super Hero LIVE at Tigin Irish Pub(10pm-1am)
• 🕸️🕷️Stamford: Blood-Manor(6pm-10pm)
• 🌽South Windsor: Foster Family Farm Corn Maze(10am-6pm)
• 🌽Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm)
• 🎨🍂🧶Windsor: Windsor Outdoor Fall Festival(10am-5pm)
• 🌽🎃🚜Windsor: Pumpkin Patches, Hay Rides and Mazes / Corn at Brown's Harvest(10am-5pm)
• Woodbury: Nashville Drive LIVE at the Woodbury Brewing Company(8pm)
• Westport: Emma's Revolution at Voices Cafe(8pm-10:30pm)
• Westport: Jukebox Radio LIVE at Black Duck Cafe(9:30pm) 

Sunday, November 2nd

• 👑🍾💃Bethel: DRAG BRUNCH - HALLOWEEN STYLE LIVE at Shakedown Street Eats(11am)
• 📣Bridgeport: Wine N Chill at The Redline Room(3pm-9pm)
• Bridgeport: Candice Guardino's ITALIAN BRED(5pm)
• Bridgeport: Scott Murray LIVE at BRYAC(6pm)
• Danbury: Bill Dempsey LIVE at Charter Oak Brewing(3pm-5pm) 
• Danbury: LISA GUTKIN & SUE HOROWITZ at Music at the Ridge(4pm-6pm)
• 🎃Easton: Pumpkin Patch at Silverman's Farm(9am-5pm)
• 🌽🎃🚜Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm)
• 🎃Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm)
• New Milford: Dan Sawyer LIVE at Housatonic River Brewing(4pm-7pm)
• 👻New Haven: Ghosts of New Haven(7:30pm)
• 📣Newtown: Chocolate Fondue Dip & Sip at Aquila's Nest Vineyards(11am)
• 📣Newtown: Sourdough 101 Class at Aquila's Nest Vineyards(11am)
• 📣Newtown: Greek Live Music Family Night at Aquila's Nest Vineyards(2pm)
• 📣Newtown: The Psychedelic Relics Tribute Show at Aquila's Nest Vineyards(4pm)
• Newtown: Judson Jazz LIVE at Reverie Brewing(2pm-5pm)
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) 
• Port Chester, NY: Jason Bonham’s Led Zeppelin Evening LIVE at The Capitol Theatre(8pm)
• Pawling,NY: Bruce T Carroll Trio LIVE at Daryl's House(12pm)
• Pawling,NY: Morgan James - Soul Remains Tour LIVE at Daryl's House(7pm) 
• 🎃Ridgefield: Jesse Lee Pumpkin Patch(10am)
• 🎨🍂🧶Southbury: Southbury New Age and Craft Fair(5pm) 
• 🤣📣Stamford: Comedians Brandon Barrera, Matt Benjamin, Caitlin Reese, Vannessa Jackson at New York Comedy Club Stamford (7pm)
• 🌽South Windsor: Foster Family Farm Corn Maze(10am-6pm)
• 🌽🎃🚜Windsor: Pumpkin Patches, Hay Rides and Mazes / Corn at Brown's Harvest(10am-5pm)