Oktoberfest

Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States

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, music and entertainment for all ages!

Free

Event Series Blessing of the Animals

Blessing of the Animals

Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United States

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 place in front of the church, rain or shine. All pets need to be leashed or in carriers. Washington Irving, author of “The Legend of …

Free

Frightening Food Truck Friday the 13th

Sleepy Hollow River Walk Park Westward Drive, Sleepy Hollow, NY, United States

What better day to have some fun down at the new RiverWalk Park than Friday the 13th. FRIGHTENING FOOD TRUCK FRIDAY THE 13th takes place on October 13th from 5pm-9pm. Guests of all ages are invited to come down for live music, food trucks, ice cream, vendors and even a visit from The Headless Horseman. …

Free

KCBC Monster Mash

Beekman Ale House 92 Beekman Avenue, Sleepy Hollow, NY

Kings County Brewers Collective and Beekman Ale House join up for an evening of KCBC brews, thin crust pizza, vinyls by grizmostgreet, and Halloween movies in the beer garden. 5 pm until . . .

Postponed Sleepy Hollow Street Fair

Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY, United States

The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Sleepy Hollow Street Fair takes place this year on Saturday, October 14th, transforming Beekman Avenue into a huge outdoor market. Nearly 100 vendors draw thousands of visitors! October is the most exciting time to visit Sleepy Hollow. The weeks leading up to Halloween have something for everyone: haunted hayrides, …

Free

Sleepy Hollow Street Fair

Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY, United States

The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Sleepy Hollow Street Fair takes place this year on Saturday, October 14th, transforming Beekman Avenue into a huge outdoor market. Nearly 100 vendors draw thousands of visitors! October is the most exciting time to visit Sleepy Hollow. The weeks leading up to Halloween have something for everyone: haunted hayrides, …

Free

Halloween Psychic & Vendor Faire

Cozy Coven 267 A Central Avenue, White Plains, NY

Psychic readings and local crafters come together at Cozy Coven's 2023 Faire. Consult readers and healers, shop bewitching goods, and enjoy food trucks and baked goods.

Free

Christ Church Fall Fair

Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United States

Christ Episcopal Church in Tarrytown, where Washington Irving worshipped, brings back its Fall Fair in 2023! Shop books, clothing, jewelry, toys and more. Stop by the International Café and Bake Sale for delicious home made food. Plus there are crafts and games for children. The all-day event is from 10 am to 4 pm. The …

Free

Rivertowns SUP & Yoga Witch Festival

Horan's Landing Park 57 River Street, Sleepy Hollow, NY, United States

Searching for a wicked sight? Come to Horan’s Landing Waterfront Park for the 4th Annual SUP Witch Paddle where the witches gather and “The Legend of Sleepy Hollow” is told. Join the witches on the water or stroll along the Riverwalk and watch the witches pass by. Vendors, food, brews & spooky views! A memorable …

Free

A Goosefeather Halloween

Goosefeather 49 E Sunnyside Lane, Tarrytown, United States

Calling all Ghouls & Boos for Goosefeather's Halloween party! Well-behaved pets are welcome. If they are also in costume - even better! Food and Beverages will be available for purchase. This event will take place on the Front Lawn of the restaurant. Candy Hunt, which begins promptly at 12PM. 2 Bounce Houses, one for little …

$15

Piermont Oktoberfest

Village of Piermont Piermont, NY, United States

Directly across the Hudson River from Washington Irving's home Sunnyside, the Village of Piermont throws an OKTOBERFEST for all to enjoy! There is authentic German food and beer, live music, boutique shopping, art exhibits, kids activities and much, much more! Please note, this event is 9 miles from downtown Sleepy Hollow, across the Governor Mario …

Free

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.