One of the most wonderful things about autumn in New York isn’t the city itself—it’s the opportunity it brings to get away with a simple hop and skip across a bridge or tunnel, and land within hours (or even minutes) at a charming town or isolated stretch of nature awash in beautiful reds, oranges, and yellows. Whether it’s a short jaunt north to the quaint town of Nyack—so close to the city you could trade in the car for a bicycle to get there—or a long and leisurely trip to Vermont (what some consider to be the American capital of leaf-peeping), these fall road trips will have you relishing every minute of autumnal bliss.
The Berkshires
The drive up to this region—which spans more than 2,000 square miles across Massachusetts and part of Connecticut—is an exercise in decompression. Roll the windows down to take it all in: the scent of lavender and wildflowers, the sounds of birds chirping and hawks calling, and the views of changing maples, oaks, and pines. That nature is on full display whether you’re staying at Miraval Berkshires, a new wellness resort set on 380 acres where you can throw hatchets, zipline through the forest, and hike to your heart’s content, or at the Granville House, a new four-bedroom inn run by two Union Square Hospitality Group alumni (don’t miss the duo’s just-sweet-enough olive-oil muffins at breakfast). You could hike for days on incredible trails to sites like Monument Mountain and Bartholomew’s Cobble, but there’s also plenty to stay in town for too. The restaurants of the Berkshires offer a blend of big-city charm and farm-fresh style, from Prairie Whale (Brooklyn restaurateur Mark Firth’s Great Barrington spot highlighting seasonal produce and meats) to Café Boulud at Blantyre (acclaimed chef Daniel Boulud’s new dining room at the famed hotel in Lenox). Don’t miss the Old Inn on the Green or John Andrews either, two more restaurants that take advantage of the Berkshires’ natural bounty (and beauty) with sprawling grounds and organic dishes.
Related: The Best New England Towns to See the Changing Autumn Leaves
North Fork, New York
For all the fuss made about the Hamptons, the buzz around its neighbor, North Fork, has only recently begun. The northern end of a Long Island—separated from the Hamptons and the “south fork” by the Peconic River—is quieter and more in tune with nature than its southern counterpart, but no less entertaining for a long weekend, especially in the fall, after the summer crowds have dissipated. One thing the North Fork excels at is wine, and you can sample the best of its 50-plus wineries by starting in Southold at Mattabella Vineyards (known for its sustainably made chardonnays) and Sparkling Pointe (exceptional rosés and blancs de blancs), and ending in Greenport at Kontokosta (whose lawn on an oceanfront promontory is the perfect place to catch the changing colors of fall). Greenport is also home to many of North Fork’s best restaurants—don’t miss the lounge-style American Beech and seafood-focused Frisky Oyster—but part of the local charm here is stepping away from the see-and-be-seen scene and getting to know the local farmers, many of whom are young and applying innovative techniques, like at Garden of Eve, a 100 percent organic farm that employs permaculture practices. Stay within walking distance of nearly everything in town by checking in at the Menhaden, a chic design boutique hotel with views over the Peconic and a guest-only rooftop deck.
Nyack, New York
No car? No problem. New York City’s quaint commuter towns offer a wonderful way to get out of the city and glimpse some changing leaves without a set of wheels. Catch the Metro North Hudson line, bicycle along scenic Route 9, or hike straight up the Long Path (a gorgeous riverfront trail that runs from the George Washington Bridge all the way to Albany) to arrive in the little town of Nyack, where a weekend of fall activities may include kayaking on the Hudson River—right under the Tappan Zee Bridge if you like—and hiking in Nyack Beach State Park. The village is also home to the Edward Hopper House: The mid-19th-century residence built by the artist’s maternal grandfather that exhibits contemporary artists and also features a section devoted to Hopper’s early works. Saunter down Main and Broadway streets to shop at vintage and mom-and-pop boutiques like the beloved Pickwick Book Shop, and sample the region’s farm-fresh ingredients at Simard and Co. wine and cheese shop and the Henry, the town’s newest restaurant serving local specialties like Nyack poutine along with creative cocktails. Overnight just a few miles north in Haverstraw, at Casa Hudson, an elegant and modern bed-and-breakfast set within a restored 19th-century Italian Renaissance villa.
Related: Why North Fork, Long Island Is the Perfect Weekend Trip Destination
Finger Lakes, New York
You could come to this upstate region just to sample its famous rieslings—but there’s much more to do than sip whites in this bucolic getaway named for its five pristine lakes. Station yourself in Aurora, the charming little hamlet that’s home to Inns of Aurora, a collection of stunning historic estates turned hotels. The newest property in town is Zabriskie House, a colorful 11-bedroom retreat tucked behind the grand white pillared façade of a circa-1904 manse. From there, it’s an easy amble to all of Aurora’s attractions, including the 1833 Kitchen & Bar overlooking Cayuga Lake and Vintage Lighting, a treasure trove crammed with crystal chandeliers and antiques. Nearby, is the mecca of eclectic country-chic, Mackenzie Childs, where hand-painted ceramics and imaginative furnishings are displayed in a whimsical showroom surrounded by acres of parkland. Immerse yourself in the changing colors of fall with a hike in Watkins Glen State Park, where the dozens of trails take you to crashing waterfalls and vast gorges. Of course, you can’t come this way and not sample the wine: Make sure Hermann J. Wiemer—one of the defining wineries of the region, producing dry rieslings reminiscent of Germany’s Mosel Valley—is on your list. And for a taste of the Finger Lakes’ next generation of winemakers, schedule a guided session in Forge Cellar’s new tasting room. The winery’s small-production, terroir-distinct pinot noirs are fast gaining a reputation for being some of the region’s best.
Central Vermont
Vermont is practically synonymous with autumn. With forests covering three-quarters of the state, and a greater abundance of maple trees than anywhere else in the U.S., it’s no wonder leaf-peeping revelers flock her every fall. Post up at Twin Farms, an all-inclusive resort set on 300 private acres of forest, and surround yourself with autumnal beauty. Hike miles of private trails, canoe or fish in Cooper Pond, or take a gourmet picnic on a mountain-biking excursion through the Green Mountains. You can also cycle straight to Woodstock—the historic town is a 10-mile downhill ride—and go back in time with a stroll past antique shops and F.H. Gillingham & Sons, a general store that first opened its doors in 1886 (make sure to stock up on Vermont maple syrup while you’re there). For more comfort food, stop by Sugarbush Farm to sample Vermont Sage and Mountain Jack cheese made right on the 500-acre grounds. Then make a stop in nearby Quechee at Simon Pearce to pick up the glassblower’s famed tableware and dine at its restaurant cantilevering over the Ottauquechee River waterfall.
