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Kick off the Holiday season on December 2nd with the third annual Sleepy Hollow and Tarrytown Winter Stroll! Extended shopping hours, outdoor dining, story telling, holly jolly trolley, holiday treats, …
The Village will be closing down Main Street to cars and opening it up to shopping, dining, strolling, and more on three Sundays this year. Come out to celebrate Mom …
This event offers a delightful blend of nostalgia and respect for Sleepy Hollow's automotive heritage, featuring an impressive array of classic vehicles that have left an indelible mark on the …
Event date moved from May 12! The Village will be closing down Main Street to cars and opening it up to shopping, dining, strolling, and more on three Sundays this …
Join Philipsburg Manor for a day filled with art, poetry, live music, dance, and storytelling that celebrates and commemorates the region’s African American history and culture. Hear a spoken word …
On Saturday, June 1, the historic Christ Church San Marcos, an Episcopal Church in Tarrytown, invites Westchester residents to connect with organizations making a positive impact in their communities. Day …
Join Lyndhurst Mansion on June 8th and 9th from 10 am to 3 pm to experience the blooming Rose Garden and to spend some time in the fresh air! Certain …
The Headless Horseman rides again, but this time he’s heading for the main stage at Sleepy Hollow’s Kingsland Point Park, with its breathtaking view of the Hudson River, for the …
Join Lyndhurst Mansion on June 8th and 9th from 10 am to 3 pm to experience the blooming Rose Garden and to spend some time in the fresh air! Certain …
The Village will be closing down Main Street to cars and opening it up to shopping, dining, strolling, and more on three Sundays this year. Enjoy live music and activities …
Celebrating Bread from Africa to the Americas Take your tastebuds on a trip around the world and sample breads from countries around the globe, from eba to empanadas. Meet with …
Participate in the area’s first ever land and water parade! March through the park in costume or float on stand up paddle boards and kayaks on the Hudson. After the …
Get ready for the most epic Block Party of the year! Everyone’s invited to the Sleepy Hollow Block Party on Saturday, Sept. 14, from 2 pm – 10 pm! Join …
The Village will be closing down Main Street to cars and opening it up to shopping, dining, strolling, and more on three Sundays this year. Enjoy live music and activities …
Stein Hoisting contests, live OomPah music, Oktoberfest games, beer & food specials! Best part? FREE ADMISSION! So grab your friends, throw on your lederhosen, and get ready to party with …
Stein Hoisting contests, live OomPah music, Oktoberfest games, beer & food specials! Best part? FREE ADMISSION! So grab your friends, throw on your lederhosen, and get ready to party with …
Don't miss the 4th annual Croton Oktoberfest, right around the corner from The Great Jack O'Lantern Blaze! This event transforms Grand Street into a full-fledged Bier Garden while The Croton …
Feast on German food and beer from local eateries and dance to live Bavarian music at Sleepy Hollow's annual Oktoberfest! Cider and hot chocolate is offered for the younger set, …
Blessing of the Animals brings together furry friends, fish & fowl, snakes, bugs, zebras & elephants. Pets and people of all faiths, and no faith, are welcome! The Blessing takes …
Searching for a wicked sight? Come to Kingsland Point Park for the 5th annual SUP Witches Paddle where the witches gather and “The Legend of Sleepy Hollow” is told. Join …
For a little pre-Halloween fun, decorate your vehicle and give out candy to children of the community dressed in costumes! A best decorated car prize will be awarded. To participate, …
Halloween Block Party featuring Halloween crafts, games, a mirror maze, face painting, and shopping/activities for adults, including a beer garden hosted by Climbing Wolf! Also included are two 30-minute Rivertowns Playhouse performances of Rip Van Winkle …
Christ Episcopal Church in Tarrytown, where Washington Irving once worshipped, is thrilled to bring back its Fall Fair in 2024! From 10 am to 4 pm, visitors can shop for …
The Good Witch Coffee Bar's Scarecrow’s Ball is an all-day, Oz-themed Halloween extravaganza with a dash of magic and a sprinkle of mischief. It’s got everything from “witchy” brews to …
Photo by Jessie Spellman Mignone. Join us for a magical evening at the Tarrytown and Sleepy Hollow Winter Stroll! Experience the charm of the season as our historic towns come …
There's something for everyone in Sleepy Hollow Country—farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.