From Classic Rock to Halloween: October Heats Up at Edmond Town Hall

Halloween season is creeping into Connecticut and the Hudson Valley with haunted trails, glowing pumpkins, ghostly legends, historic cemeteries and plenty of things that go bump in the night. Fairfield After Dark has rounded up some of our Hot Picks for Halloween Adventures in and around Fairfield County — from family-friendly pumpkin spectaculars to attractions made for those who really like a good scare. 👻 FAIRFIELD COUNTY Legends of Fear — Shelton One of Connecticut’s major Halloween attractions combines a Haunted Hayride with The Hallow Trail, elaborate scenes, actors and plenty of nighttime scares. Fright Haven — Stratford More than 20,000 square feet of indoor scares make Fright Haven a great choice when you want a haunted-house experience without worrying about October weather. Harvest Fair After Dark — Fairfield A local Halloween adventure featuring a haunted hayride, wooded trails and multiple nighttime attractions. A Haunting at Mill Hill — Norwalk History meets Halloween with lantern-lit encounters and chilling stories inspired by Norwalk’s past. 🎃 NEW HAVEN COUNTY Trail of Terror — Wallingford One of Connecticut’s longtime Halloween favorites sends visitors through an enormous outdoor haunted trail filled with elaborate scenes and live scares. Evidence of Evil — Middlefield Lyman Orchards gets sinister after dark with an immersive haunted attraction featuring theatrical sets, characters and plenty of surprises. Haunted Trolley — East Haven The Shore Line Trolley Museum puts a uniquely Connecticut spin on Halloween with its nighttime haunted trolley experience. 🍂 LITCHFIELD COUNTY Scarecrows in the Meadow — Litchfield | Oct. 17–Nov. 1 More than 50 creative, funny and spooky scarecrows take over the historic Tapping Reeve Meadow. Open daily from dawn to dusk and FREE to visit. This is a great choice for families looking for Halloween fun without the fright factor. 🎃🐎 FAD ROAD TRIP: SLEEPY HOLLOW COUNTRY If Halloween had a hometown, Sleepy Hollow would have a pretty strong claim to the title. For 2026, Sleepy Hollow Country has created an entire Halloween season around Washington Irving, Ichabod Crane and, of course, the legendary Headless Horseman. ⭐ FAD HOT PICK: Twilight Village at Sleepy Hollow | Oct. 2–31 Historic Philipsburg Manor transforms after dark into an immersive Halloween village filled with storytellers, fire performers, eerie encounters, a roving brass band, evening market and a dramatic encounter with the Headless Horseman . 🔎 Headless Horseman Files | Oct. 2–31 Here’s something completely different! Become part of the mystery surrounding the disappearance of Ichabod Crane. Visitors explore Philipsburg Manor, meet suspects including Katrina Van Tassel, Brom Bones and Hulda the Witch, gather clues and decide what really happened. ✨ Spirits of Sleepy Hollow Country | Oct. 2–31 Illusionists Mark Clearview and Nick Wallace bring magic and the supernatural together in another new Sleepy Hollow experience centered around the legendary Horseman. 🎃 Great Jack O’Lantern Blaze — Croton-on-Hudson | Sept. 18–Nov. 8 More than 7,000 hand-carved jack-o’-lanterns illuminate ten acres at Van Cortlandt Manor. New for 2026 is a longer trail with additional displays, movie-monster photo opportunities, storybook characters and a pumpkin dance party. This one is spooky rather than scary , making it a great choice for families. 👻 Sleepy Hollow Haunted Hayride | Oct. 17 Want your Sleepy Hollow experience a little scarier? Take a haunted hayride through the village that made the Headless Horseman famous. ⚰️ Sleepy Hollow Cemetery Explore one of America’s most famous cemeteries — and the final resting place of Washington Irving — with seasonal daytime and evening guided tours. 🏰 Lyndhurst Mansion — Tarrytown Halloween and Gothic architecture were made for each other. Lyndhurst adds seasonal Halloween programming to one of the Hudson Valley’s most dramatic historic estates. FAD TIP: There is enough happening throughout Sleepy Hollow, Tarrytown, Irvington and Croton-on-Hudson to turn this into a complete Halloween day trip — or an overnight getaway. 👻 PUTNAM COUNTY, NY Spellbound — Carmel Head into the woods for a different kind of Halloween adventure combining a haunted trail with live entertainment, fire performances and a Mystic Market atmosphere. Putnam makes an especially easy Halloween road trip from Danbury, Ridgefield and northern Fairfield County. 🎃 DUTCHESS COUNTY, NY Kevin McCurdy’s Haunted Mansion — Wappingers Falls | Oct. 2–Nov. 1 This Hudson Valley Halloween institution celebrates its 50th season in 2026 with an expanded outdoor walk-through adventure through an eerie forest, ghost town, cemetery and monster-filled environments. Haunted Beacon Ghost Walk — Beacon Grab a lantern and explore the darker side of Beacon through local ghost stories, legends, historic locations and tales of paranormal activity. Ages 16+ due to mature subject matter. Stony Kill Farm Spooktacular — Wappingers Falls A family-oriented Dutchess County Halloween tradition bringing seasonal fun to the historic farm setting. 👻🎃 FAD’S HALLOWEEN ADVICE Whether you want glowing pumpkins, a haunted hayride, an all-out haunted attraction or an entire weekend immersed in the legend of the Headless Horseman, there is no shortage of Halloween adventures within driving distance of Fairfield County. But if you're planning one Halloween road trip for 2026, Sleepy Hollow Country deserves serious consideration. Many Halloween attractions require timed tickets, and popular October weekends can sell out. Always check dates, age recommendations and ticket availability before heading out. Happy Haunting from Fairfield After Dark! 👻🎃🐎

STAMFORD, CT: The Palace Theatre has a packed October lineup featuring live music, comedy, ballet and tribute performances. From the sounds of the Bee Gees and Prince to some of today's touring comedians and classic rock favorites, there’s plenty happening in downtown Stamford this month. October 2 – Stayin' Alive Stayin' Alive kicks off the month at 8 PM with a tribute to the Bee Gees, featuring favorites like Night Fever , How Deep Is Your Love , You Should Be Dancing and Stayin' Alive . October 9 – Brad Williams Comedian Brad Williams brings his Tall Tales Tour to The Palace at 7 PM. Williams has appeared on The Tonight Show , Jimmy Kimmel Live and numerous comedy specials. October 10 – The Purple Xperience Marshall Charloff & The Purple Xperience celebrates the music of Prince at 8 PM with a high-energy live performance featuring some of his biggest hits. October 15 – Yedoye Travis Comedian, writer and actor Yedoye Travis takes the stage at 7:30 PM. His latest hour-long comedy special, Fatherless Behavior , was released in 2026. October 16 – Anthony Rodia Anthony Rodia brings his Insanely Funny Tour to Stamford at 8 PM, delivering his signature take on family, relationships and everyday life. October 17 – Snow White and the Seven Dwarfs Step into the magical world of Snow White and the Seven Dwarfs, one of the most beloved fairytales of all time, brought to life in a dazzling Broadway-style ballet production filled with beauty, humor, adventure, and theatrical magic. October 22 – Matteo Lane Matteo Lane brings his WE GOTTA CATCH UP! Tour to The Palace at 8 PM for an evening of stand-up and storytelling. October 23 – Killers of Kill Tony Killers of Kill Tony hits the stage at 8 PM featuring David Lucas, Martin Phillips, Ahren Belisle and David Jolly performing extended stand-up sets. October 30 – America: The Happy Trails Tour Classic rock favorites America arrive at 7 PM with The Happy Trails Tour . Fans can look forward to music from the band's decades-long career, including the iconic A Horse With No Name . The Palace Theatre 61 Atlantic Street, Stamford, CT

Sandy Hook/Newtown, CT: Aquila’s Nest Vineyards has another busy week ahead with FREE live music, food trucks, wine pairings, DJ Bingo, comedy and more. Whether you're looking for a casual night of wine and music or something a little different, there’s plenty happening at the vineyard. Thursday, September 24 Start the weekend early with FREE live music from Dr. Neil from 5:30–8:30 PM , with Feeling Saucy Pasta Food Truck on-site. Thursday Happy Hour also features 20% off wine by the glass, slushies, sangrias and mocktails from 4–6 PM. Friday, September 25 Friday’s ticketed experiences include a Brownies & Wine Pairing , Brie Blossom Foodie Night and Speed Dating for ages 25–39. Or simply grab a glass of wine and enjoy FREE live music from Round Two Duo from 5:30–8:30 PM , with The Crepe Hut Round serving up Friday’s food. Saturday, September 26 Saturday brings a Mini Fall Pies & Wine Pairing , followed by FREE live music with Acoustic Mafia from 2:30–5:30 PM. Taste of Mediterranean and Greek Crave food trucks will also be on-site. At 6:30 PM, turn back the clock with the ticketed Back to School 80s & 90s DJ Bingo. Sunday, September 27 Finish the weekend with Plant Bingo and a Cheesecakes & Wine Pairing. RAE Duo performs FREE from 2–5 PM , with Cousins Maine Lobster and The Mason Jar Exchange serving up Sunday’s food. Then at 7 PM, Aquila’s wraps up the weekend with a ticketed Comedy Night inside the tasting room. Wine, Food & FREE Music All Weekend From wine pairings and food trucks to DJ Bingo, comedy and FREE live music Thursday through Sunday, Aquila’s Nest Vineyards has plenty of reasons to visit this week. Aquila’s Nest Vineyards | 56 Pole Bridge Road | Sandy Hook/Newtown, CT Ticketed experiences can fill up, so reserve early. 👉 CLICK HERE FOR AQUILA’S NEST VINEYARDS’ FULL SCHEDULE & EVENT DETAILS

Stamford, CT: Looking for some good laughs this week? New York Comedy Club Stamford has a packed lineup heading into the weekend, with Gareth Reynolds taking the stage Thursday night, followed by four shows with W. Kamau Bell on Friday and Saturday — plus even more comedy throughout the weekend. Thursday Night: Gareth Reynolds The laughs get started Thursday, September 24 at 7 PM with internationally touring comedian Gareth Reynolds , best known as co-host of the hit podcast The Dollop alongside Dave Anthony. Reynolds has worked across television, film, podcasts and stand-up, with credits including New Girl, Arrested Development, I’m Sorry, You’re the Worst and Maron. His debut stand-up album, Riddled With Disease, reached No. 1 on the Billboard comedy charts. W. Kamau Bell Takes Over Friday & Saturday The weekend brings W. Kamau Bell to Stamford with his latest stand-up show, Who’s With Me? Bell, a stand-up comedian and filmmaker, is widely known as the former host and executive producer of CNN’s five-time Emmy Award-winning United Shades of America. His return to stand-up mixes observations, questions and plenty of humor as he takes on life in today’s hectic world. And Fairfield County comedy fans have four chances to catch him : Friday, September 25: 7 PM & 9:30 PM Saturday, September 26: 7 PM & 9:30 PM The Friday & Saturday 7 PM premium seating is already sold out , while tickets remain available for other seating categories and performances as of September 23. Start Saturday with Some Early Laughs Want to get your comedy fix before dinner? Early Bird Comedy hits the stage Saturday, September 26 at 4:30 PM . The showcase brings together a host and a lineup of comedians, giving audiences that classic comedy-club experience where several different styles of stand-up share the same stage. Make It a Comedy Night in Stamford From Gareth Reynolds on Thursday to four opportunities to see W. Kamau Bell Friday and Saturday, there are plenty of reasons to add some laughs to your weekend plans.  New York Comedy Club Stamford 230 Tresser Blvd., Stamford, CT Check out the complete lineup and grab your tickets directly from New York Comedy Club Stamford — popular performances can fill up quickly.

Black Rock - Bridgeport, CT: