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
NEWTOWN, CT: October is packed with entertainment at Edmond Town Hall , with live music, comedy, movies, special events and Halloween fun filling the historic Newtown theater throughout the month. October 2 – That 70’s Show 3DR Presents: That 70’s Show kicks things off at 8 PM with a celebration of the arena-rock sounds of the 1970s, including music from Queen, ELO, Chicago, the Eagles and more. October 3 – Smells Like Nirvana Smells Like Nirvana hits the stage at 7:30 PM, recreating the music and energy of one of the most influential bands of the grunge era. October 4 – Newtown Record Riot Vinyl lovers can browse thousands of LPs from 9 AM–4 PM, along with vintage clothing, artwork, food, beer and more. Proceeds benefit Edmond Town Hall. October 8 – The Lightfoot Band The Lightfoot Band performs at 7 PM, featuring musicians who recorded and toured with Gordon Lightfoot for decades. October 9 – Amanda Knox Exoneree, journalist, author and podcast host Amanda Knox comes to Newtown for a special evening beginning at 7 PM. October 10 & 11 – Movie Weekend Catch The Rocky Horror Picture Show Saturday at 7:30 PM, followed Sunday at 1 PM by a FREE matinee of Anaconda starring Jack Black and Paul Rudd, courtesy of Ingersoll Auto of Danbury. October 16 – Classic Stones Live Classic Stones Live celebrates the music of The Rolling Stones at 7:30 PM with an evening of rock & roll favorites. October 17 – The Linda Ronstadt Experience American Idol alum Tristan McIntosh and a full band celebrate Linda Ronstadt’s remarkable catalog at 8 PM. October 23 – John Oates Rock & Roll Hall of Famer John Oates and the Good Road Band perform at 7:30 PM in a special concert benefiting the Connecticut Cancer Foundation. October 24 – Rocky Horror Live The Rocky Horror Picture Show returns at 7:30 PM, this time accompanied by a live shadow cast from the Come Again Players . October 25 – Music & Comedy The Waterbury Symphony Orchestra presents The Haunting of Edmond Town Hall from 2–4 PM. Later that evening, comedian Gary Gulman takes the stage for his SOLD-OUT performance. October 30 – The Grand Slambovian Halloween Ball Close out the month at 8 PM with The Grand Slambovian Halloween Ball , featuring The Slambovian Circus of Dreams and a night of rock, Americana and Halloween fun. Edmond Town Hall 45 Main Street, Newtown, CT edmondtownhall.org.
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
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
NEWTOWN, CT: October is packed with entertainment at Edmond Town Hall , with live music, comedy, movies, special events and Halloween fun filling the historic Newtown theater throughout the month. October 2 – That 70’s Show 3DR Presents: That 70’s Show kicks things off at 8 PM with a celebration of the arena-rock sounds of the 1970s, including music from Queen, ELO, Chicago, the Eagles and more. October 3 – Smells Like Nirvana Smells Like Nirvana hits the stage at 7:30 PM, recreating the music and energy of one of the most influential bands of the grunge era. October 4 – Newtown Record Riot Vinyl lovers can browse thousands of LPs from 9 AM–4 PM, along with vintage clothing, artwork, food, beer and more. Proceeds benefit Edmond Town Hall. October 8 – The Lightfoot Band The Lightfoot Band performs at 7 PM, featuring musicians who recorded and toured with Gordon Lightfoot for decades. October 9 – Amanda Knox Exoneree, journalist, author and podcast host Amanda Knox comes to Newtown for a special evening beginning at 7 PM. October 10 & 11 – Movie Weekend Catch The Rocky Horror Picture Show Saturday at 7:30 PM, followed Sunday at 1 PM by a FREE matinee of Anaconda starring Jack Black and Paul Rudd, courtesy of Ingersoll Auto of Danbury. October 16 – Classic Stones Live Classic Stones Live celebrates the music of The Rolling Stones at 7:30 PM with an evening of rock & roll favorites. October 17 – The Linda Ronstadt Experience American Idol alum Tristan McIntosh and a full band celebrate Linda Ronstadt’s remarkable catalog at 8 PM. October 23 – John Oates Rock & Roll Hall of Famer John Oates and the Good Road Band perform at 7:30 PM in a special concert benefiting the Connecticut Cancer Foundation. October 24 – Rocky Horror Live The Rocky Horror Picture Show returns at 7:30 PM, this time accompanied by a live shadow cast from the Come Again Players . October 25 – Music & Comedy The Waterbury Symphony Orchestra presents The Haunting of Edmond Town Hall from 2–4 PM. Later that evening, comedian Gary Gulman takes the stage for his SOLD-OUT performance. October 30 – The Grand Slambovian Halloween Ball Close out the month at 8 PM with The Grand Slambovian Halloween Ball , featuring The Slambovian Circus of Dreams and a night of rock, Americana and Halloween fun. Edmond Town Hall 45 Main Street, Newtown, CT edmondtownhall.org.
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
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
NEWTOWN, CT: October is packed with entertainment at Edmond Town Hall , with live music, comedy, movies, special events and Halloween fun filling the historic Newtown theater throughout the month. October 2 – That 70’s Show 3DR Presents: That 70’s Show kicks things off at 8 PM with a celebration of the arena-rock sounds of the 1970s, including music from Queen, ELO, Chicago, the Eagles and more. October 3 – Smells Like Nirvana Smells Like Nirvana hits the stage at 7:30 PM, recreating the music and energy of one of the most influential bands of the grunge era. October 4 – Newtown Record Riot Vinyl lovers can browse thousands of LPs from 9 AM–4 PM, along with vintage clothing, artwork, food, beer and more. Proceeds benefit Edmond Town Hall. October 8 – The Lightfoot Band The Lightfoot Band performs at 7 PM, featuring musicians who recorded and toured with Gordon Lightfoot for decades. October 9 – Amanda Knox Exoneree, journalist, author and podcast host Amanda Knox comes to Newtown for a special evening beginning at 7 PM. October 10 & 11 – Movie Weekend Catch The Rocky Horror Picture Show Saturday at 7:30 PM, followed Sunday at 1 PM by a FREE matinee of Anaconda starring Jack Black and Paul Rudd, courtesy of Ingersoll Auto of Danbury. October 16 – Classic Stones Live Classic Stones Live celebrates the music of The Rolling Stones at 7:30 PM with an evening of rock & roll favorites. October 17 – The Linda Ronstadt Experience American Idol alum Tristan McIntosh and a full band celebrate Linda Ronstadt’s remarkable catalog at 8 PM. October 23 – John Oates Rock & Roll Hall of Famer John Oates and the Good Road Band perform at 7:30 PM in a special concert benefiting the Connecticut Cancer Foundation. October 24 – Rocky Horror Live The Rocky Horror Picture Show returns at 7:30 PM, this time accompanied by a live shadow cast from the Come Again Players . October 25 – Music & Comedy The Waterbury Symphony Orchestra presents The Haunting of Edmond Town Hall from 2–4 PM. Later that evening, comedian Gary Gulman takes the stage for his SOLD-OUT performance. October 30 – The Grand Slambovian Halloween Ball Close out the month at 8 PM with The Grand Slambovian Halloween Ball , featuring The Slambovian Circus of Dreams and a night of rock, Americana and Halloween fun. Edmond Town Hall 45 Main Street, Newtown, CT edmondtownhall.org.
