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October 11, 2025
Briarcliff Manor, NY

Jaina & Michael

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    Things To Do

Things To Do

The Wedding Website of Jaina Maher and Michael Urquhart
October is this town’s time to shine. Sleepy Hollow is known for the legend of the Headless Horseman, and if you're a Halloween enthusiast (or just enjoy a cozy fall vibe), it's a pretty fun place to be this time of year. That said—just to be clear— save the spooky stuff for the rest of the weekend. The wedding activities are not Halloween-themed 😉

Legend of the Headless Horseman

Read more about the Headless Horsemen here. Or don't if you get nightmares from scary stories like Michael does.

Tarrytown & Sleepy Hollow Farmers Market

Patriot's Park, Tarrytown, NY

Visit the local farmers market on Saturday morning to sample fresh Hudson Valley produce, baked goods, and artisanal products.

Sleepy Hollow Cemetery

540 North Broadway, Sleepy Hollow, NY 10591

Take a walk through the historic cemetery, visiting the gravesites of notable figures like Washington Irving and Andrew Carnegie. Or don't. Michael wouldn't.

Rockefeller State Park Preserve

Tower Hill Road, Pleasantville, NY 10570

Enjoy the fall foliage along over 45 miles of scenic carriage trails.

Philipsburg Manor

381 North Broadway, Sleepy Hollow, NY 10591

You can walk around the grounds of Philipsburg Manor, but to go inside buildings like the manor house, gristmill, and barn, you’ll need to join a guided tour. During October, special events like the Legend of Sleepy Hollow Discovery Walk and Horseman’s Hollow are available, and require tickets.

Tarrytown Waterfront

Take a stroll along the Tarrytown waterfront

Washington Irving's Sunnyside

3 West Sunnyside Lane, Irvington, NY 10533

Visit the charming estate designed by Washington Irving, enjoy guided tours, and take in the beautiful gardens.

Headless Horseman Bridge

415 North Broadway, Sleepy Hollow, NY 10591

Walk across the iconic bridge that Washington Irving wrote about in his tales, perfect for photos and scenic views.

Places to Eat & Drink

Sleepy Hollow / Tarrytown, NY

Eattarry Barely on the Hudson RickerMarket Bar and Kitchen Horsefeathers Beekman Ale House The Tapp

For all the days along the way
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