7 Beautiful Fall Day Trips from NYC

To capture that fallscape selfie of the moment, head to Beacon’s Storm King Art Center, a 500-acre large-scale sculpture garden that stretches across bucolic hills, woodlands, and wildflower fields in the heart of Hudson Valley—just an hour-and-a-half train or car ride from Manhattan. The leaf-peeping here is second to none, but it’s also worth carving out some time to check out Dia:Beacon, a beautiful, light-filled former box-printing factory turned museum showcasing an impressive collection of 60s-era art by the likes of Richard Serra and Andy Warhol. Is it happy hour already? Dennings Point Distillery for a taste of their artisanal whiskeys; afterwards, retreat to the Roundhouse for dinner (stout-braised pork cheeks; an autumn salad of heirloom carrots, young beets, and roast pear dressing) with a view of Beacon Falls.

Antiquing is a favorite fall pastime, and there’s arguably no better place to do it than the pastoral towns of rural Connecticut—Kent, Goshen, Litchfield—which are known for their independent retailers and barns turned storefronts. Base yourself at Winvian Farm, a beautiful country retreat whose 18 cottages, designed by various architects, take on a unique theme—one is built inside a tree house, for example, while another takes after a nautical lighthouse. All have fireplaces and access to the property’s spa and surrounding meadows, where staff lead horseback rides or snowshoeing treks come winter. Have a taste for wine? Litchfield's Haight-Brown Vineyard pairs their chardonnays and bold reds with cheeses and chocolates.

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Interested in trading cities for a day? It’s time to ditch the car (who needs traffic, anyway?) and hop a train for the 90-minute journey to Philly. We all know the city’s great history—Hello Liberty Bell! Hello Independence Hall! Hello Elfreth's Alley! (America's oldest inhabited street)—but the food scene here is making a serious case for itself, from Michael Solomonov’s acclaimed Israeli restaurant  Zahav to French-New American at Top Chef alum Nicholas Elmi’s Laurel—one of the hottest tickets in town. A great place to start your tour is Rittenhouse Square, a beautiful park in the center of it all. Be sure to catch a glimpse of the Cy Twombly works at Philly’s Museum of Art before retiring to Wm. Mulherin’s Sons for even more incredible food (oxtail agnolotti; corn ravioli with ricotta and chive) and the chance to sleep it off in one of the four stylish bedrooms upstairs.

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Philip Johnson’s Glass House is a kind of design-lover’s mecca, but you don’t have to be an architecture major to appreciate the beauty of this 47-acre estate and ground-breaking all-glass home, just an hour by train outside the city. The grounds come alive in September, when New England’s legendary foliage begins to turn; take it all in during a stroll through the rooms and satellite galleries housing 20th-century paintings. For even more immersion, follow up your visit with a spin by Grace Farms, a cultural center by Pritzer Prize-winning Japanese architecture firm SANAA whose serpentine glass structure (housing an amphitheater, café, gym, tea pavilion, and library) emerges seamlessly from the hilly landscape. Afterwards, rest your legs at the charming Homestead Inn in nearby Greenwich, where the real star is the elevated French cuisine served at its Thomas Henkelmann restaurant.

With Halloween just around the corner, there’s no better time to plan a trip up the river to Sleepy Hollow—where American author Washington Irving based “The Legend of Sleepy Hollow.” You’ll find his grave at the local cemetery—along with a few other notable natives including Astors and Rockefellers. At the weekly farmer’s market, you can pick up pumpkins, wines, cheeses, and glimpse locations that inspired Irving’s horror story. (For even more fear factor, book a tour at Horseman’s Hollow, open seasonally every October, for a fright-filled through a haunted house. It’s a far less spooky affair in nearby Tarrytown at Blue Hill at Stone Barns, where guests are treated to ingredient-driven tasting menus sourced right here in Hudson Valley.

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Wondering where Richard Gere has gone to after his bouts with Hollywood? At least some of his time, we imagine, is dedicated to the upkeep of the Bedford Post Inn, an eight-room sleep in Westchester he co-owns with his ex-wife and a friend. Everything here feels as much an escape as he intended: the forested grounds are quiet and secluded, the pool is beautiful and serene, the yoga studio is airy and bright and the guest rooms are rustic and charming, many with mosaic-tiled bathrooms and fireplaces. Even if you aren’t looking to stay awhile it’s worth stopping in for a meal at one of the two country-chic restaurants for seasonal American cuisine and live piano music.

Manhattan’s summer weekenders that crowd onto Asbury Park’s beach and boardwalk fizzle out by fall—all the better, we say, for enjoying a sunset cocktail on the roof at the Asbury Hotel (or a game at Asbury Lanes) without the competing riffraff. While years of neglect saw Bruce Springsteen’s hometown disappear into the shadows, a recent surge of development—including said hotel and the new Asbury Festhall & Biergarten—has put it back on the map. By fall, the Atlantic might be too chilly for a dip, but afternoons are better spent strolling the boardwalk and hitting all the great stops, including the legendary Stone Pony and Antique Emporium for all your thrifting vintage needs.