How to Spend a Perfectly Spooky Saturday in Sleepy Hollow

Visitors flock to this Hudson River-facing village for gorgeous foliage, Halloween events, and to celebrate Washington Irving.

Adobe Stock / lspi138

It’s that time of year when visitors flock to the riverfront village for gorgeous foliage and superb Halloween events in Westchester.

By Samantha Garbarini, Anthony Tornatore, and Ryan Noel

In October, visitors flock to this Hudson River-facing village for gorgeous foliage, Halloween events, and a celebration of Washington Irving’s famous literary work, “The Legend of Sleepy Hollow.” Whether you’re looking for a lantern tour, a journey through a historic estate, or just a spooky hayride, this is the Halloween town for you. What’s more, these events paired with meals from some of the village’s top eateries are a match made in heaven. So, pack your bags and enjoy your Saturday in Sleepy Hollow.

9 a.m. – Grab something sweet from Los Andres Bakery

Grab a quick bite at Los Andes Bakery (180 Valley St.; 914.631.3256). The Chilean shop — look for a sign reading simply “Valley Bakery” — serves traditional pastries like flaky empanadas and sweet alfajores, a.k.a. buttery cookies held together by a layer of dulce de leche.


View this post on Instagram


A post shared by Rub It Til It Smokes (@ritisbbq)

- Advertisement -

10 a.m. – Head to the Sleepy Hollow Cemetery

Pick up a free map at the south gate or office to help you navigate the 90 arboreal acres of Sleepy Hollow Cemetery (540 N Broadway; 914.631.0081). Among the tombstones and stone angels, you’ll find grand mausoleums belonging to titans of industry and the monied elite, including Walter Chrysler, William Avery Rockefeller, and Harry and Leona Helmsley. Also buried here: Elizabeth Arden, Brooke Astor, Andrew Carnegie, and the cemetery’s most popular interment, Washington Irving. Or you can sign up for a guided tour of the cemetery.

11 a.m. – See where the Headless Horseman haunts Sleepy Hollow

Near the Sleepy Hollow Cemetery is the Old Dutch Church and Burying Grounds (430 N Broadway), the fabled haunt of the Headless Horseman and the resting place of residents thought to have inspired the characters in Irving’s “The Legend of Sleepy Hollow.” If it’s open, pop into the still-functioning Old Dutch Church, a National Historic Landmark, to admire its 17th-century Dutch Colonial interior.


View this post on Instagram


A post shared by (@sleepyhollowspellbound)

12 p.m. – Have lunch at the Bridgeview Tavern

Head to Bridgeview Tavern (226 Beekman Ave.; 914.332.0078) for a leisurely lunch in the beer garden. Pair any of the restaurant’s craft beers or ciders on draft — Hill Farmstead, Southern Tier Pumking, Hudson North Standard, Foam Drops, and more — with wings, burgers, or our favorite “Disco Is Dead” fries, the latter which come loaded with wild-boar-chorizo chili, cheese, pickled jalapeños, and bacon.


View this post on Instagram


A post shared by @bridgeviewtavern

- Partner Content -

2 p.m. – Take a tour of Philipsburg Manor 

Across the street from the Sleepy Hollow Cemetery sits Philipsburg Manor (381 N Broadway; 914.366.6900), a mill and trading complex where an enslaved community lived and labored for generations. Guided tours of the manor last about an hour and 40 minutes and run from 10 a.m. to 3:30 p.m.


View this post on Instagram


A post shared by Claudine (@ccountryatheart)

4 p.m. – Check out the Sleepy Hollow Lighthouse 

The Sleepy Hollow Lighthouse was built in the 1880’s and lies right along the Hudson River, making it the perfect spot for a pre-dinner stroll. Along the RiverWalk you can catch picturesque views of the Governor Mario M. Cuomo Bridge as it sits behind the lighthouse, an ideal Instagrammable spot. There’s metered parking on Beekman Ave and paid parking in Kingsland Point Park.


View this post on Instagram


A post shared by Tatiana (@_tani.photography_)

- Advertisement -

5 p.m. – Enjoy dinner at Hudson Farmer & the Fish

Nab a waterfront table by the RiverWalk at Hudson Farmer & the Fish (11 River St.; 914.631.8380), where chef-owner Michael Kaphan sources the freshest seafood and harvests seasonal produce from his other restaurant-farm, Purdy’s Farmer & the Fish in North Salem. Order a bottle of white, anything and everything from the raw bar, some salads, and a thin-crust mushroom pizza, and you’re set for the rest of the night.

7 p.m. – Watch The Legend, a Cirque Theatre Performance

After you fill up on much-needed grub, go back in time to the 1800s with this immersive experience. “The Legend” is an adaptation of Washington Irving’s classic ghost story, “The Legend of Sleepy Hollow.” This event is back by popular demand and incorporates holograms of Washington Irving and the iconic Headless Horseman. The holograms are paired with circus performances by the Westchester Circus Arts.

9 p.m. – Rest at the Tarrytown House Estate on the Hudson

Located a few minutes from Sleepy Hollow, this four-star hotel embodies elegance reminiscent of America’s Gilded Age. Overlooking the Hudson River, the Tarrytown House Estate (49 E Sunnyside Ln; 914.591.8200) is a haven for recreation and relaxation. Hit the tennis court, shoot some hoops, or take a dip in the pool. If the hunger pangs hit, order a fantastic meal at Goosefeather, where you can enjoy modern, seasonal Chinese fare made by Chef Dale Talde.

Related: 6 Westchester Cemeteries Filled With Beauty and History

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.