💀 From Frights to Festivities: The Best Halloween & Live Music Events This Weekend

🎃 Your Ultimate Halloween & Live Music Weekend Guide in and around Fairfield County 👻

Get ready for a weekend packed with spooks, sounds, and seasonal fun! Fairfield County is buzzing with Halloween happenings — from haunted attractions and ghost tours to pumpkin patches, costume parties, and live music galore. Whether you’re looking to dance the night away, explore something spooky, or make family memories under the fall sky, there’s something for everyone this weekend. 

Local breweries and bars are hosting costume bashes and creepy cocktail nights, theaters are showing classic horror flicks, and historic venues are bringing back ghostly gatherings you won’t want to miss. 

👻 Thrill-seekers can brave haunted trails and scream parks popping up across the county. Check out FAD’s full Halloween Events List for all the eerie details! 

🎃 Families can enjoy trick-or-treat events, pumpkin patches, and fall festivals — all featured in our Halloween Calendar. 

🍸 Night owls can dance the night away at masquerade balls, bar crawls, and live DJ sets. Find all the music and nightlife highlights in our Live Music Calendar. 

So grab your costume, round up your ghoul gang, and get ready for a frightfully good time! This is your ultimate guide to all the fun and fear happening in and around Fairfield County this Halloween weekend. 

🕸️ Stay spooky — and remember, some events sell out faster than a witch on a broomstick, so plan ahead! FAD also features a daily roundup of what’s happening in towns across Fairfield County — so keep scrolling and enjoy! 

Wednesday, October 22

• 🎃📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm)
• Bethel: Jerry Vivino (Springsteen, Marsalis) Quintet LIVE at La Zingara(7pm)
• 🎃Bethel: Blue Jay Orchards PYO Pumpkins & Wagon Rides(11am-5pm)
• 🎃Fairfield: Enchanted Castle at the Burr Mansion(9:30am)
• 🎃📣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: Witchy Wednesdays at Aquila's Nest Vineyards (6-9pm)
• 🎃North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm)
• Pawling, NY: J.D. Leonard & Co. LIVE at Daryls House(7pm) 
• Port Chester, NY: Modest Mouse LIVE at the The Capitol Theatre(8pm) 
• 🎃South Windsor: Foster Family Farm Corn Maze(10am-6pm)
• 📣Stamford: Connor O'Malley at New York Comedy Club Stamford(7pm-9:30pm)
• 🎃Tarrytown, NY: Ghost Tours of The Music Hall 2025 LIVE at Tarrytown Music Hall(10:30pm) 
• 🎃Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm)

Thursday, October 23

• 🎃📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm)
• Bethel: Open Mic Night at Molten Java(7pm-9pm)
• 🎃Bethel: Blue Jay Orchards PYO Pumpkins & Wagon Rides(11am-5pm)
• Danbury: Line Dancing every Thursday night at Elicit Brewing Danbury(7pm)
• Danbury: Thursday Open Jam w/Sugar House LIVE at Sugar Hallow Taproom(8pm-11pm)
• Fairfield: FAKE ID LIVE at The Sinclair(8:30pm)
• 🎃📣Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm)
• 🎃Higganum: Pumpkin Patch at Halfinger Farms(9am-6pm)
• Milford: Pete Grossi LIVE at Cafe Atlantique(5pm-8pm)
• 🎃Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm)
• 🎃North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm)
• 📣Newtown: Girl Scout Cookies & Wine Pairing at Aquila's Nest Vineyards(6pm)
• 📣Newtown: Comedian Stephen Kellogg comes to Edmond Town Hall(8pm-10pm)
• Norwalk: Live music with STEVEN KEITH!(5:30pm-8:30pm)
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
• Norwalk: Sheila & Ray LIVE at The Sandbar(6:30pm-8:30pm) 
• Pawling, NY: Remember Tomorrow - Iron Maiden Tribute LIVE at Daryls House(8pm) 
• Ridgefield: Chris Cavaliere LIVE at Nod Hill Brewery(6pm)
• Shelton: Happy Sally LIVE at Pier 131(7pm-10pm)
• 🎃South Windsor: Foster Family Farm Corn Maze(10am-6pm)
• 📣Stamford: Comedians Jilberto Soto, Chris Scopo, Tyler Groce, Olivia Carter at New York Comedy Club Stamford (7pm)
• 🎃Tarrytown, NY: Ghost Tours of The Music Hall 2025 LIVE at Tarrytown Music Hall(11am)
• 🎃Tarrytown, NY: Ghost Tours of The Music Hall 2025 LIVE at Tarrytown Music Hall(12pm)
• 🎃Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm)
• 🎃Wilton: Victorian Mourning Customs(7pm-8pm)
• Westport: Tim Horner LIVE at Jazz at the Post(7:30pm-10pm)
• Westport: The Outsiders LIVE at Black Duck Cafe(9:30pm)

Friday,October 24,

• Bethel: Roving Son LIVE at Shakedown Street(6:30pm)
• Bethel: Mike & Ike 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)
• 🎃Derby: All Hallows Emo Night LIVE at Badsons Beer(7pm) 
• Danbury: Peter and His Band of Wolves LIVE at Charter Oak Brewing(7pm-9pm)
• 📣Danbury: Peter Antonio The Psychic Comedian at The Palace Danbury Theatre(8pm)
• Danbury: Line Dancing at Molly Darcy's(8pm-11pm)
• Danbury: 80s New Music Night LIVE at Sugar Hallow Taproom(8:30pm)
• Danbury: Flannel Clad Masses LIVE at Elicit Brewing Danbury(9pm)
• Danbury: DJ GOLDEN BOY LIVE at Elicit Brewing Danbury(10pm)
• 🎃Fairfield: Monsters Ball Elicit Brewing Company in Fairfield(6pm) 
• Fairfield: Between The Keys LIVE at Elicit Brewing Fairfield(9pm)
• Fairfield: DJ DONNY D in the Speakeasy at Elicit Brewing Fairfield(10pm)
• 🎃Fairfield: Harvest Fair Halloween Haunt(7pm-10pm)
• Greenwich: Halloween Happenings at the Greenwich Civic Center(5:30pm-7:30pm)
• 🎃📣Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm)
• 🎃Higganum: Pumpkin Patch at Halfinger Farms(9am-6pm)
• Milford: John Young LIVE at Cafe Atlantique(6:30pm-9:30pm)
• 🎃Milford: 16th annual Hall-O-Weekend Fall Festival(6:30pm-3pm)
• Milford: EMILY MAGER BAND LIVE at Stonebridge Restaurant(7pm)
• 🎃Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm)
• 🎃North Salem, NY: Mystic Moon at Harvest Moon Farm and Orchards(7pm)
• 🎃North Branford: Rose Orchards Corn Maze & Pumpkin Patch(7am-6pm)
• New Milford: Way Behind the Sun LIVE at Housatonic Brewery(7pm-10pm)
• 🎃New Haven: Ghosts of New Haven(7:30pm)
• 📣Newtown: Brownies & Wine Pairing at Aquila's Nest Vineyards(6pm)
• 📣Newtown: Wine and Wheels - Showcase Your Car at Aquila's Nest Vineyards(6pm)
• 🎃📣Newtown: Grapeyard Scavenger Hunt Glow Night at Aquila's Nest Vineyards(6:30pm)
• Newtown: Emma's Plight LIVE at Reverie Brewing(6pm-9pm)
• Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm)
• 📣Newtown: Karaoke Wine Night at Aquila's Nest Vineyards(7pm)
• 📣Newtown: The Rocky Horror Picture Show(7:30pm-11pm)
• Newtown: Crash 21 LIVE at Perfusion Bar(8pm-11pm)
• 📣Norwalk: CHRISTOPHER CAVALIERE LIVE at SONO 1420(6pm-9pm)
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) 
• Norwalk: Captain Obvious LIVE at 314 Beer Garden(7pm-11pm) 
• Old Greenwich: The Romero Brothers Band LIVE at Bosco's Bar & Grill(9pm-12am)
• Port Chester, NY: Colbie Caillat & Shawn Colvin Raising The Bar Benefit Concert LIVE at the The Capitol Theatre(8pm)
• Pawling, NY: High Noon – A Night of Southern Rock LIVE at Daryls House(8pm)
• Redding: Joey & Zully LIVE at The Redding Roadhouse(7pm-10pm)
• 🎃Ridgefield: Ghosts of Ridgefield at Keeler Tavern Museum & History Center(5pm-7pm)
• Ridgefield: Jon Pousette LIVE at Nod Hill Brewery(7pm)
• 🎃📣Ridgefield: Paranormal Park Ghost Walk in Richardson Park, Ridgefield(7pm)
• Rowayton: Pimpinella LIVE at Sails American Grill(9:30pm)
• 🎃Rye, NY: Scarded By The Sound at Playland(8pm-11pm)
• 🎃South Windsor: Foster Family Farm Corn Maze(10am-6pm)
• Shelton: The Rahsaan Langley Project LIVE at Pier 131(9pm-12am)
• Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm)
• 🎃Stamford: Haunted House Party(6pm-8pm)
• 📣Stamford: Comedian Drew Lynch at New York Comedy Club Stamford (4 shows!)(7pm-9:30pm)
• Stamford: Rock Paper Soul LIVE at Bobby V's(7pm-10pm)
• 📣Stamford: Josh Johnson at The Palace Stamford(8pm)
• Stamford: Justin Neafsey Trio LIVE at Third Place by Half Full Brewery(8pm-10pm)
• Stamford: Bad Management LIVE at Tiernan's Bar(9:30pm)
• Stamford: Club Shebeen at Tigin Irish Pub(10pm)
• 🎃Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm)
• Woodbury: BADFOOT LIVE at the Woodbury Brewing Company(8:30pm)
• Westport: N.O.S. Band LIVE at Black Duck Cafe(9:30pm) 

Saturday,October 25

• Bethel: Newtown Rock This Democracy LIVE at Shakedown Street(6:30pm)
• Bethel: Iris Lies LIVE at Notch 8(8pm)
• 🎃📣Bethel, NY: Peace, Love & Pumpkins at Bethel Woods Center for the Arts(6:30pm-10pm) 
• 🎃📣Bridgeport: BOO at the Zoo!(11am-3pm) 
• 🎃Danbury: Halloween on the Green(1pm-4pm)
• Danbury: Go 2 Eleven LIVE at Charter Oak Brewing(6pm-8pm)
• Danbury: DJ PICKZ LIVE at Elicit Brewing Company Danbury(10pm)
• 🎃Easton: Pumpkin Patch at Silverman's Farm(9am-5pm) 
• 🎃East Windsor: Pumpkin Patch at Connecticut Trolley Museum(10am-4pm)
• Fairfield: Ashes & Arrows LIVE at StageOne FTC(7pm-8pm)
• Fairfield: DJ DURSO in the Speakeasy at Elicit Brewing Fairfield(10pm)
• 🎃Fairfield: Harvest Fair Halloween Haunt(7pm-10pm)
• 🎃Goshen: Fall Festival on the Zoo Farm - Action Wildlife Foundation(10am-5pm)
• 🎃📣Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm)
• 🎃Litchfield: Bunnell Farm Corn Maze & Pumpkin Patch(10am-5pm)
• Milford: Tim Payson LIVE at Cafe Atlantique(6:30pm-9:30pm)
• 🎃Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm)
• 🎃North Salem, NY: Mystic Moon at Harvest Moon Farm and Orchards(7pm)
• New Milford: Strange Souls - A Tribute to The Doors LIVE at Housatonic Brewery(7pm-10pm)
• 🎃New Haven: Ghosts of New Haven(7:30pm)
• 🎃New Milford: Scarrybrooke Park CT's Haunted Trail(6pm)
• 🎃Newtown: Fall Festival at Castle Hill Farm(10am-5pm)
• 📣Newtown: Fine Pastries and Wine 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 Vineyards(7pm) 
• 🎃📣Newtown: The Rocky Horror Picture Show | Featuring Shadow Cast at Edmond Town Hall(7:30pm-11pm)
• Newtown: Tobacco Road LIVE at Perfusion Bar(8pm-11pm)
• 🎃Newtown: Night Corn Maze at Castle Hill Farm(5pm-8pm)
• 🎃Norwalk: Beasties and Besties Halloween Bash at Stepping Stones Museum for Children(10am-5pm)
• 🎃Norwalk: Halloween at the Lab(2pm-9pm) 
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
• Norwalk: That Guy Larry LIVE at Odeen’s Norwalk(7pm)
• 🎃Norwalk: Graveyard Bash ft. Badboy at 314 Fear Garden(7pm-11pm)
• Old Greenwich: Frankie and the Soundcats LIVE at Bosco's Bar & Grill(9pm-12am)
• Pawling, NY: La Pompe Attack LIVE at Daryls House(12pm-2pm)
• Pawling, NY: Jessica Lynn LIVE at Daryls House(8pm)
• Port Chester, NY: Daniel Donato's Cosmic Country LIVE at the The Capitol Theatre(8pm)
• 🎃Redding: Halloween Party at Granite(7pm-10pm)
• 🎃Ridgefield: Ghosts of Ridgefield at Keeler Tavern Museum & History Center(5pm-7pm) 
• 🎃Ridgefield: Ridgefield’s Annual Halloween Walk(10am-12pm) 
• 🎃📣Ridgefield: Paranormal Park Ghost Walk in Richardson Park, Ridgefield(7pm)
• 🎃South Windsor: Foster Family Farm Corn Maze(10am-6pm)
• Shelton: Da’ Band LIVE at Pier 131(9:30pm-12am) 
• 🎃Shelton: Legends of Fear(7pm) 
• Sherman: The Funk Express LIVE at JCC In Sherman(7pm-9pm)
• 📣Stamford: The Concert: A Tribute to ABBA at The Palace Stamford(8pm)
• Stamford: Pimpinella LIVE at Tiernan's Bar(9:30pm)
• 🎃Stamford: Blood-Manor(6pm-10pm)
• Stratford: The In Laws LIVE at Windmill Tavern(8pm) 
• 🎃Torrington: Moonlight Masquerade Dracula Ball(8pm)
• 🎃Thompson: Fort Hill Farms Corn Maze Adventure(12pm-4pm)
• Woodbury: Limelight: A Tribute to RUSH at the Woodbury Brewing Company(8:30pm)
• 🎃Windsor: Pumpkin Patches, Hay Rides and Mazes / Corn at Brown's Harvest(10am-5pm)
• Westport: Retro Express LIVE at Black Duck Cafe(9:30pm)

Sunday October 26

• Bethel: Brunch with Michael Bram LIVE at Shakedown Street(12pm)
• Bethel: Grennan Bros LIVE at Notch 8(4pm)
• Danbury: The Angry O’Haras LIVE at Charter Oak Brewing(2:30pm-5:30pm)
• 🎃Easton: Pumpkin Patch at Silverman's Farm(9am-5pm) 
• 🎃East Windsor: Pumpkin Patch at Connecticut Trolley Museum(10am-4pm)
• 🎃Fairfield: PIPESCREAMS! MUSICAL EXTRAVAGANZA(2pm-3pm)
• 🎃Goshen: Fall Festival on the Zoo Farm - Action Wildlife Foundation(10am-5pm)
• 🎃📣Guilford: Bishop's Orchards Corn Maze & Hay Ride(9am-5pm)
• 🎃Litchfield: Bunnell Farm Corn Maze & Pumpkin Patch(10am-5pm)
• 🎃Middlefield: Lyman Orchards Corn Maze & Pumpkin Picking(1pm-5:30pm)
• New Milford: The Resounders LIVE at Housatonic Brewery(4pm-7pm)
• 🎃New Haven: Ghosts of New Haven(7:30pm)
• 📣Newtown: Taylor Swift Cover Band Family Show at Aquila's Nest Vineyards(12pm)
• 📣Newtown: Chris Kalafus LIVE at Aquila's Nest Vineyards(2pm-5pm) 
• Newtown: Rich Molden LIVE at Reverie Brewing(4pm-7pm)
• 🎃Newtown: Fall Festival at Castle Hill Farm(10am-5pm)
• 🎃📣Newtown: Hocus Pocus Need Wine to Focus Drag Show at Aquila's Nest Vineyards (6:30pm)
• 🎃Norwalk: Halloween Kid’s Jam at 314 Fear Garden(12pm-2pm)
• Norwalk: Pimpinella LIVE at 314 Beer Garden(2:30pm-6pm)
• Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm)
• 🎃New Canaan: Halloween Block Party on Elm Street, New Canaan(12pm-2pm)
• Pawling, NY: Bob Stump LIVE at Daryls House(12pm)
• Pawling, NY: Grunge Night Unplugged - The Greatest Hits of MTV Unplugged LIVE at Daryls House(7pm) 
• 🎃Ridgefield: Ghosts of Ridgefield at Keeler Tavern Museum & History Center(5pm-7pm)
• 🎃Ridgefield: Jesse Lee Pumpkin Patch(10am)
• South Windsor: Foster Family Farm Corn Maze(10am-6pm)
• 📣Stamford: Comedian Wyatt Feegrado at New York Comedy Club Stamford(7pm)
• 🎃Windsor: Pumpkin Patches, Hay Rides and Mazes / Corn at Brown's Harvest(10am-5pm)
• Woodbury: Troy Millette LIVE at the Woodbury Brewing Company(1pm)
• 🎃Weston: FRANKENSTEIN, The Modern Prometheus at Lachat Town Farm(6pm)