Timeout New York Kids

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Field trip to Sleepy Hollow and Tarrytown, NY

Explore historic sites, fine artwork and The Legend of Sleepy Hollow in these two upstate locales. 

  • Photograph: Bryan Haeffele

    Philipsburg Manor House

  • Photograph: Bryan Haeffele

    Philipsburg Manor House

  • Photograph: Bryan Haeffele

    Historic Sunnyside Manor

  • Union Church of Pocantico Hills

  • Photograph: Tom O'Connell

    Historic Sunnyside Manor

Photograph: Bryan Haeffele

Philipsburg Manor House


After a trip on the Metro-North Hudson line to Tarrytown, take a cab ride to Sleepy Hollow ($6). Kids will get a primer on the town's obsession with America's creepiest author by grabbing breakfast at The Horseman (276 N Broadway, Sleepy Hollow; 914-631-2984). Order the challah French toast and peruse the photographs of local sights while you wait.


Walk over to the Visitor Center (381 N Broadway, Sleepy Hollow; 914-631-3992, hudsonvalley.org) and purchase tickets for both Philipsburg Manor and Sunnyside (combination tickets $18, children ages 5–10 $9). Then circle the mill pond on the Woodland Path, which transports visitors to the 1750s via a tour of the Philipsburg Manor House led by a costumed guide. The museum inside tackles tough issues like slavery but it also keeps kids' interests thanks to a number of hands-on activities. Little ones are invited to partake in daily tasks like grinding herbs, brushing oxen and churning butter.


Grab sandwiches at All Fleet Deli (358 N Broadway, Sleepy Hollow; 914-909-5522) and bring them to the riverfront Kingsland Point Park (299 Palmer Ave), where a gazebo, a playground and the Sleepy Hollow Lighthouse await.


Next, cab it ($10) to the lush grounds of Sunnyside (89 W Sunnyside Ln, Irvington; 914-631-8200, hudsonvalley.org), the estate on which Washington Irving designed and built the cottage he lived in from 1835 to 1859. Ask the staff to lend you one of their Traveling Totes; the kit includes a scavenger hunt and games for kids. Magicians, shadow puppeteers and musicians will also be on hand throughout October as part of the Legend Celebration. Before heading out, stop by the gift shop for children's adaptations of Rip Van Winkle and The Legend of Sleepy Hollow.


Enjoy the temperature clash of hot chocolate la mode at Main Street Sweets (35 Main St, Tarrytown; 914-332-5757), an $8 cab ride from Sunnyside. Then browse the town's strip of charming shops and galleries. Impressive student artwork is on display at Studio A Gallery (52 Main St, 914-412-2955); A Nu Toy Store (36 Main St, 914-372-7144) has a dollhouse and train table to occupy kids while parents check out the vintage Star Wars figures and original Smurfs.


Another cab trip ($10) takes your crew to the quaint Union Church of Pocantico Hills (555 Bedford Rd, Pocantico Hills; 914-631-2069. $5 per person). The church boasts nine stained glass windows by Marc Chagall. Though his name might not mean anything to your kids, the bright colors will impress even the youngest art critics.


Have dinner at Sweet Grass Grill (24 Main St, Tarrytown; 914-631-0000, sweetgrassgrill.com)—a $10 ride from Pocantico Hills—before making your way back to the Tarrytown train station. The menu changes often since the chefs rely on area farms for their organic ingredients. Favorites include Hudson Valley duck for adults and free-range chicken fingers for younger day-tripping diners.

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