Adventures to unearth in Tarrytown, NY
Where even the squirrels have a must-do list!
This is a calendar of upcoming events and things to do.
See our list of Fun things to do happening all the time.
Oct 3 (Thurs) Tarrytown Music Hall 8pm.
Music Artist - Rick Wakeman - Final Solo Tour
Oct 3 (Thurs) Karaoke 8pm at The Tapp (A fun local bar)
Every Thursday we sing! Karaoke starts at 8 pm with a classic ice breaker. Warm up then choose your favorites from thousands of songs.
Oct 4 (Fri) Sleepy Hollow Rock n Roll House of Horrors 5-11pm.
The Headless Horseman and his band await you on stage!
Be our VIP and brave six terrifying rooms backstage filled with unspeakable horrors to reach the final destination—a photo op with the legendary Headless Horseman! Only the boldest will survive. Do you have what it takes? Oct 4-Nov 2
Buy your tickets now, if you dare! More info and tickets https://house-of-horrors.squadup.com/
Oct 4 (Fri) Tarrytown Music Hall 8pm.
Music Artist - Dianne Reeves & Romero Lubambo Duo
Oct 5 (Sat) TaSH Farmers Market 8:30am-1:30 at Patriots Park.
Farm-fresh fruits and vegetables, artisanal breads and baked goods, meats, poultry, fish, craft spirits, farmhouse cheeses – it’s all here. But that’s just where it starts. Each Saturday, May through November, more than 30 vendor stalls hug a sun-dappled, grassy lawn, where the best area musicians entertain. Kids dance and play, friends and families socialize, and everyone eats! We host chef demos, art projects, children’s activities and we welcome our fellow non-profit organizations to share their good works too. Enjoy FREE parking at John Paulding School, across the street from the market on Route 9. Enter via Sleepy Hollow High School driveway and bear right at the fork. Look for the TaSH parking signs!
Oct 5 (Sat) Rocky's 5K Run 9am
Beautiful fall foliage is the perfect backdrop for Rocky's 5K. Challenging hills and wide carriage roads - the perfect race for experienced trail runners and first-timers. If you are familiar with the Rockies, test your stamina and charge those uphills! First 5K? The well-marked course and friendly volunteers will make it enjoyable from start to finish.
Oct 5 (Sat) Scarecrow Making 10:45am-11.45 & 12pm-1 at Tarrytown
Scarecrow Making.
Oct 5 (Sat) Sleepy Hollow Street Fair 10am-4 on Beekman Ave.
175+ Vendors, Arts and Crafts, Food and Entertainment for the entire family…pooches included! Halloween and Holiday items too!
Oct 5 (Sat) Sleepy Hollow Rock n Roll House of Horrors 5-11pm.
The Headless Horseman and his band await you on stage!
Be our VIP and brave six terrifying rooms backstage filled with unspeakable horrors to reach the final destination—a photo op with the legendary Headless Horseman! Only the boldest will survive. Do you have what it takes? Oct 4-Nov 2
Buy your tickets now, if you dare! More info and tickets https://house-of-horrors.squadup.com/
Oct 5 (Sat) Tarrytown Music Hall 8pm.
Music Artist - The Machine Performs Pink Floyd
Oct 6 (Sun) Walk For Wishes Hudson Valley Registration 8:30am at Kingsland Point Park, Sleepy Hollow
18th Annual Walk for Wishes walkathon! 🎉🌟 Join us for a spooktacular day of hope and joy! 🎃👟 Scenic walk along the Hudson River
Halloween activities including facepainting, costume contest, and more.
Glass pumpkin patch hosted by Adirondack Glassblowing Studio between Oct 3-6. Entertainment and delicious treats.
Oct 6 (Sun) Tarrytown Music Hall 7pm.
Music Artist - Neko Case w/ Special Guest Imaad Wasif.
Oct 7 (Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)
Come watch Monday Night Football with us or grab one of our board games and have some fun. Choose from Chess, Checkers, Connect 4, Candyland, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
Oct 8 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
Oct 10 (Thurs) Tarrytown Music Hall Times vary.
2024 SLEEPY HOLLOW INT'L FILM FESTIVAL - The acclaimed SLEEPY HOLLOW INTERNATIONAL FILM FESTIVAL (SHIFF) returns!!! A celebration of outstanding genre cinema in the historic cradle of the American Supernatural, SHIFF showcases FEATURE FILM and SHORT FILM PREMIERES, SPECIAL ANNIVERSARY SCREENINGS, IN-PERSON GUESTS AND MORE!
Oct 10 (Thurs) Karaoke 8pm at The Tapp (A fun local bar)
Every Thursday we sing! Karaoke starts at 8 pm with a classic ice breaker. Warm up then choose your favorites from thousands of songs.
Oct 11 (Fri) Tarrytown Music Hall Times vary.
2024 SLEEPY HOLLOW INT'L FILM FESTIVAL - The acclaimed SLEEPY HOLLOW INTERNATIONAL FILM FESTIVAL (SHIFF) returns!!! A celebration of outstanding genre cinema in the historic cradle of the American Supernatural, SHIFF showcases FEATURE FILM and SHORT FILM PREMIERES, SPECIAL ANNIVERSARY SCREENINGS, IN-PERSON GUESTS AND MORE!
Oct 12 (Sat) Tarrytown Music Hall Times vary.
2024 SLEEPY HOLLOW INT'L FILM FESTIVAL - The acclaimed SLEEPY HOLLOW INTERNATIONAL FILM FESTIVAL (SHIFF) returns!!! A celebration of outstanding genre cinema in the historic cradle of the American Supernatural, SHIFF showcases FEATURE FILM and SHORT FILM PREMIERES, SPECIAL ANNIVERSARY SCREENINGS, IN-PERSON GUESTS AND MORE!
Oct 13 (Sun) Witches Festival & Paddleboard Parade 12-5pm at Kingsland Point Park
Witches on Paddleboards and a big party!! See the headless horseman, costume contest, food & vendors, live music.
Oct 13 (Sun) Tarrytown Music Hall Times vary.
2024 SLEEPY HOLLOW INT'L FILM FESTIVAL - The acclaimed SLEEPY HOLLOW INTERNATIONAL FILM FESTIVAL (SHIFF) returns!!! A celebration of outstanding genre cinema in the historic cradle of the American Supernatural, SHIFF showcases FEATURE FILM and SHORT FILM PREMIERES, SPECIAL ANNIVERSARY SCREENINGS, IN-PERSON GUESTS AND MORE!
Oct 14 (Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)
Come watch Monday Night Football with us or grab one of our board games and have some fun. Choose from Chess, Checkers, Connect 4, Candyland, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
Oct 15 (Tue) Window Painting 3:30pm-5.30 at Tarrytown
Window Painting.
Oct 15 (Tues) The Purple Ostrich Adult Strategy Board Game Nights 6:30-9pm at Tarrytown Senior Center.
Join us for some board game fun with friends. We will provide some of the games available each event night and we also encourage people to bring their own games in hopes of finding someone else interested in playing that one game you can never get anyone to play with you. You'll just need to be able to teach it!! Tarrytown Senior Center/Rec Dept at 240 W Main St, Tarrytown, NY 10591 right between Pierson Park and the Train Station. Ages 18 and over.
Oct 16 (Wed) Tarrytown Music Hall 8pm.
Music Artist - Richard Thompson - Ship to Shore Tour 2024
Oct 16 (Wed) Hulda's Night Multiple times, tickets required
You walk through the night, your path lit only by lanterns. The dark woods surround you as does the chill in the night air. Your group joins a traveler around his fire and listens to local legends (The Storyteller). But your journey has only begun. This one-of-a-kind event includes 4 separate immersive performances staged along Rockefeller’s historic carriage roads. The audience, led by experienced hike leaders, walks to each location on trails lit only by lanterns.
Oct 17 (Thurs) Tarrytown Music Hall 8pm.
Music Artist - The Lone Bellow - BY REQUEST ONLY
Oct 17 (Thurs) Hulda's Night Multiple times, tickets required
You walk through the night, your path lit only by lanterns. The dark woods surround you as does the chill in the night air. Your group joins a traveler around his fire and listens to local legends (The Storyteller). But your journey has only begun. This one-of-a-kind event includes 4 separate immersive performances staged along Rockefeller’s historic carriage roads. The audience, led by experienced hike leaders, walks to each location on trails lit only by lanterns.
Oct 17 (Thurs) Karaoke 8pm at The Tapp (A fun local bar)
Every Thursday we sing! Karaoke starts at 8 pm with a classic ice breaker. Warm up then choose your favorites from thousands of songs.
Oct 18 (Fri) Trunk or Treat & Movie Night 4:30pm-6.30 & 6:45 at Tarrytown
Lot F by the rec center. Trunk or Treat & Movie Night.
Oct 18 (Fri) Tarrytown Music Hall 8pm.
Music Artist - MAGICAL MYSTERY DOORS - Beatles, Zeppelin, Doors Tribute
Oct 18 (Fri) Hulda's Night Multiple times, tickets required
You walk through the night, your path lit only by lanterns. The dark woods surround you as does the chill in the night air. Your group joins a traveler around his fire and listens to local legends (The Storyteller). But your journey has only begun. This one-of-a-kind event includes 4 separate immersive performances staged along Rockefeller’s historic carriage roads. The audience, led by experienced hike leaders, walks to each location on trails lit only by lanterns.
Oct 19 (Sat) Tarrytown Music Hall 7pm.
Music Artist - An Evening with Amanda Palmer
Oct 19 (Sat) Hulda's Night Multiple times, tickets required
You walk through the night, your path lit only by lanterns. The dark woods surround you as does the chill in the night air. Your group joins a traveler around his fire and listens to local legends (The Storyteller). But your journey has only begun. This one-of-a-kind event includes 4 separate immersive performances staged along Rockefeller’s historic carriage roads. The audience, led by experienced hike leaders, walks to each location on trails lit only by lanterns.
Oct 20 (Sun) Tarrytown Music Hall 2pm.
Entertainment - Haunted Objects Live! - Chilling, True Tales from the Newkirk Museum of the Paranormal. Are you ready to uncover the chilling true stories behind the world’s most haunted objects? Join Greg and Dana Newkirk (Travel Channel’s Kindred Spirits, Amazon Prime’s Hellier) for an interactive presentation that will leave you on the edge of your seat.
As two of the world’s only full-time paranormal investigators, the Newkirks have spent their lives collecting and caring for cursed artifacts, possessed dolls, and other creepy artifacts said to display supernatural activity. Now you can experience their spine-tingling true tales yourself!
Oct 20 (Sun) Tarrytown Music Hall 8pm.
Entertainment - Comedy Bang! Bang! - The Bang! Bang! Into Your Mouth Tour. Join host Scott Aukerman (“Mr. Show” & “Between Two Ferns: The Movie”) as he interviews celebrity guests.
Plus, the show’s open-door policy brings an assortment of eccentric oddballs and characters who pop by at any moment to chat, compete in games, and engage in comic revelry. Now entering its 15th year, this podcast has led to multiple spin-off podcasts, a New York Times best-selling book, and a beloved television series on IFC.
Oct 21 (Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)
Come watch Monday Night Football with us or grab one of our board games and have some fun. Choose from Chess, Checkers, Connect 4, Candyland, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
Oct 22 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
Oct 23 (Wed) Hulda's Night Multiple times, tickets required
You walk through the night, your path lit only by lanterns. The dark woods surround you as does the chill in the night air. Your group joins a traveler around his fire and listens to local legends (The Storyteller). But your journey has only begun. This one-of-a-kind event includes 4 separate immersive performances staged along Rockefeller’s historic carriage roads. The audience, led by experienced hike leaders, walks to each location on trails lit only by lanterns.
Oct 24 (Thurs) Tarrytown Music Hall 7:30pm.
Entertainment - Warren Miller's 75
Oct 24 (Thurs) Hulda's Night Multiple times, tickets required
You walk through the night, your path lit only by lanterns. The dark woods surround you as does the chill in the night air. Your group joins a traveler around his fire and listens to local legends (The Storyteller). But your journey has only begun. This one-of-a-kind event includes 4 separate immersive performances staged along Rockefeller’s historic carriage roads. The audience, led by experienced hike leaders, walks to each location on trails lit only by lanterns.
Oct 24 (Thurs) Karaoke 8pm at The Tapp (A fun local bar)
Every Thursday we sing! Karaoke starts at 8 pm with a classic ice breaker. Warm up then choose your favorites from thousands of songs.
Oct 25 (Fri) Tarrytown Music Hall 8pm.
Music Artist - The Robert Cray Band - Groovin’ for 50 Years!
Oct 25 (Fri) Hulda's Night Multiple times, tickets required
You walk through the night, your path lit only by lanterns. The dark woods surround you as does the chill in the night air. Your group joins a traveler around his fire and listens to local legends (The Storyteller). But your journey has only begun. This one-of-a-kind event includes 4 separate immersive performances staged along Rockefeller’s historic carriage roads. The audience, led by experienced hike leaders, walks to each location on trails lit only by lanterns.
Oct 26 (Sat) Tarrytown Halloween Parade 5:30pm From Patriots Park to Broadway and ending on Main St.
The Halloween parade is festive and fun for the whole family. Viewing along the the parade route is free and you can also participate by marching with a theme as a group or float for a chance to win prizes! Registration is required to be eligible for prizes.
Oct 26 (Sat) Tarrytown Halloween Block Party Takes place on Main St after the 5:30pm parade.
The festive block party to on Main Street with a DJ and live music, outdoor dining, performers, and much more!
Oct 28 (Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)
Come watch Monday Night Football with us or grab one of our board games and have some fun. Choose from Chess, Checkers, Connect 4, Candyland, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
Oct 29 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
Oct 30 (Wed) Tarrytown Music Hall 8pm.
Entertainment - The Vampire Circus. A mysterious, tantalizing, fun, dark, cutting-edge production guaranteed to amaze the senses. The Vampire Circus has been called a mix of circus cabaret and theater and is the result of a fusion of Tim Burton and Cirque Du Soleil. Enjoy a phenomenal night of live entertainment, based on the multidisciplinary skills of International performers showcasing theater, dance, and gymnastics. This amazing show pushes the physical boundaries of human performance and leaves audiences amazed, astounded, and astonished.
Oct 31 (Thurs) Karaoke 8pm at The Tapp (A fun local bar)
Every Thursday we sing! Karaoke starts at 8 pm with a classic ice breaker. Warm up then choose your favorites from thousands of songs.
Nov 1 (Fri) Tarrytown Music Hall 8pm.
Comedy - Preacher Lawson: Best Day Ever! Lawson is best known for his appearance on season 12 of NBC’s hit series, AMERICA’S GOT TALENT (2017) where he made it to the final round. Based off his stellar performance in season 12, Lawson was invited to compete on AMERICA'S GOT TALENT: THE CHAMPIONS (2019) and BRITAN’S GOT TALENT: THE CHAMPIONS (2019) where he advanced to the finale after receiving the most fan votes. Most recently he was handpicked by Howie Mandell to participate in AMERICA’S GOT TALENT: FANTASY LEAGUE (2024).
Nov 2 (Sat) Tarrytown Music Hall 2pm.
Entertainment - Taconic Opera - Carmen. Taconic Opera’s 27th Season in Westchester County presents everyone’s favorite opera, Carmen. Carmen is one of the most famous operas of all time. The opera tells the story of the downfall of Don José, a naïve officer, who is seduced by the fiery Carmen. José abandons his childhood sweetheart and becomes a criminal, yet loses Carmen’s love to the famous Escamillo. The opera created a scandal when first performed because of its immorality, lawlessness, and violence. It is well known for its arias “Habanera,” “Seguidilla,” and the famous “Toreador song.”
Nov 3 (Sun) Tarrytown Music Hall 1pm.
Entertainment - Taconic Opera - Carmen. Taconic Opera’s 27th Season in Westchester County presents everyone’s favorite opera, Carmen. Carmen is one of the most famous operas of all time. The opera tells the story of the downfall of Don José, a naïve officer, who is seduced by the fiery Carmen. José abandons his childhood sweetheart and becomes a criminal, yet loses Carmen’s love to the famous Escamillo. The opera created a scandal when first performed because of its immorality, lawlessness, and violence. It is well known for its arias “Habanera,” “Seguidilla,” and the famous “Toreador song.”
Nov 4 (Mon) Game Night 5pm-Mid at The Tapp (A fun local bar)
Come watch Monday Night Football with us or grab one of our board games and have some fun. Choose from Chess, Checkers, Connect 4, Candyland, Guess Who, Trivia, Cards Against Humanity and more. Have a different one in mind? Bring your own!
Nov 5 (Tues) Trivia Night 7pm at The Tapp (A fun local bar)
Free to Play! 1st & 2nd Place teams win gift certificates.
Nov 7 (Thurs) Tarrytown Music Hall 8pm.
Music Artist - Old Crow Medicine Show
Nov 7 (Thurs) Karaoke 8pm at The Tapp (A fun local bar)
Every Thursday we sing! Karaoke starts at 8 pm with a classic ice breaker. Warm up then choose your favorites from thousands of songs.
Nov 9 (Sat) Pocantico Hills Marathon & Half Marathon 8am-4pm at Rockwood Hall, Sleepy Hollow
This challenging and beautiful course begins and ends at the Rockwood Hall portion of the park overlooking the Hudson River and the Palisades. Both the half marathon and marathon are single loop courses almost entirely on wide groomed carriage roads, and the marathon visits just about all of the signature aspects of the Park Preserve with a ton of scenic views.
Nov 19 (Tues) The Purple Ostrich Adult Strategy Board Game Nights 6:30-9pm at Tarrytown Senior Center.
Join us for some board game fun with friends. We will provide some of the games available each event night and we also encourage people to bring their own games in hopes of finding someone else interested in playing that one game you can never get anyone to play with you. You'll just need to be able to teach it!! Tarrytown Senior Center/Rec Dept at 240 W Main St, Tarrytown, NY 10591 right next to both Pierson Park and the Train Station. Ages 18 and over.
Nov 29 (Fri) Trudy Dunbar 5k Turkey Trot run 9:30am at Tarrytown
Race & Walk.