Plan Your Next Long Weekend in Scenic Westchester County

The formerly hushed area along the lower Hudson River (literally home to Sleepy Hollow) is shifting into a vacation-worthy destination.

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Stone Barns Center for Food and Agriculture / Blue Hill at Stone Barns in Westchester County | Photograph by Anush Sridharan

The upper Hudson Valley (Beacon, the Catskills) has become the darling of ex-Brooklyn artists, with chic boutiques, galleries and wineries aplenty. But it turns out you can also find all this in the bucolic lower Hudson Valley, which happens to be just over a two-hour drive from Philly. The area boasts notable mansions, shoppable Main Streets and wellness spots — all along the water.

The Eating and Drinking Sitch

At Chef’s Table-featured spot Blue Hill at Stone Barns in the Pocantico Hills, there are no menus, and there is no tipping. But the dinner will still set you back $300-plus a person and likely include a “field trip” on the grounds of nonprofit Stone Barns Center for Food and Agriculture, from which most of the victuals are harvested. Not dining? They offer family-friendly farm tours, including live presentations and pop-up talks along the grounds. For dockside eats, indulge in the oysters or seafood tower at Hudson Farmer & the Fish in Sleepy Hollow. In the morning, stop at hip Coffee Labs Roasters on Tarrytown’s Main Street.

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Drinks at Captain Lawrence Brewing Co. | Photograph by Anush Sridharan

Where to Stay

Perhaps because it’s just 25 miles north of NYC, Westchester County provides an unexpected opportunity for celeb-spotting. The ritzy Castle Hotel in Tarrytown (from $319 per night) features 31 rooms overlooking the valley. It’s a historic castle — the wainscoting was supposedly shipped over from one of Louis XIV’s properties — and Scarlett Johansson, Elton John and Justin Timberlake have all stopped there. Eat at its Equus restaurant, or get a massage at the Zen-inspired Sankara Spa.

A bit further north, stay at Richard Gere’s Bedford Post Inn (from $575 per night), which books quickly since it only has eight rustic-modern rooms.

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A room at the Bedford Post Inn. Photograph courtesy Bedford Post Inn.

What to Do

For art lovers, Union Church is the best-kept secret: The unassuming exterior holds Henri Matisse’s last work and painted glass windows by Marc Chagall. If you’re itching to use your credit card, head to Katonah for clothing shops like Ebba and Catherine H. Visit Kent Decor in Bedford for home goods, and one of the country’s only Eileen Fisher Renew stores in Irvington — they stock lightly used designs reimagined in new ways.

The Can’t-Miss List

1. Explore Sleepy Hollow. The town, made famous by Washington Irving’s ghostly short story, features an 85-acre cemetery and a Headless Horseman bridge.

2. Drink at Captain Lawrence Brewing Co. Renovated last May, this brewery has a robust food menu (try the Dirty Fries) and a sprawling beer garden.

3. Practice your warrior pose at the Bedford Inn Yoga Loft. Try classes from vinyasa to sound healing to drumming.

4. See the Rockefeller estate. Wander the gardens and rooms of the “Kykuit” mansion that belonged to the richest man in America. (Scope Picasso and Warhol paintings there, too.)

5. Go bridge-spotting. Hike the just-under-two-mile 13 Bridges Loop Trail through Rockefeller State Park Preserve, which, yep, features 13 scenic bridges.

Published as “Weekending in Westchester County” in the July 2019 issue of Philadelphia magazine.