5 incredible fall getaways in the Northeast

Sep 4, 2020

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Editor’s note: As the travel industry reopens following COVID-19 shutdowns, TPG suggests that you talk to your doctor, follow health officials’ guidance and research local travel restrictions before booking that next trip. We’ll be here to help you prepare, whether you’re traveling this month or next year.


Summer may be coming to an unofficial end, but many travelers are just beginning to discover the particular joys of close-to-home road trips and easy nearcations. And fall brings a welcome respite from summer’s heat and humidity, a handful of long weekends (starting with Labor Day, Columbus Day and Thanksgiving) and glorious landscapes bursting with colorful foliage.

If you live in the Northeast, you’re especially well-positioned to take advantage of all the joys fall brings, from meals made with farm-fresh produce to leisurely, scenic drives through forests transformed into kaleidoscopic backdrops. To help you sort through the region’s spate of charming towns, we zeroed in on four destinations within driving distance of New York City, Boston and other Northeastern hubs — all with compelling reasons to visit this fall.

Just remember to bring along a good credit card for earning points on gas purchases if you’re planning on a leaf-peeping drive. With the Citi Premier℠ Card, for example, you’ll earn 3x points when you fill up, along with 3x points on many travel purchases, 2x points on dining and entertainment and 1 point per dollar on everything else.

The information for the Citi Premier card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

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The Catskills

Photo by Ben Fitchett
Photo by Ben Fitchett

Depending on where you live, you could escape to the mountainous, sometimes rural areas of the Catskills in just over two hours. This area of rippling terrain is punctuated by rambling rivers and waterfalls, making it perfect for scenic fall foliage hikes and drives.

Consider the Giant Ledge and Panther Mountain trails, near Big Indian; Kaaterskill Falls in Hunter, New York; the hike to the restored fire tower on Mount Tremper, near Phoenicia; and the Overlook Mountain trailhead just outside Woodstock.

The Catskills are in the midst of another resurgence, making it easy for even frequent visitors to experience a new, undiscovered part of the sprawling wilderness areas. Check in to the whimsical Roxbury Motel, which welcomed a significant expansion at Stratton Falls this summer. This themed experience isn’t for everyone, so for a more traditional Catskills stay, try the new Urban Cowboy Lodge in Big Indian (opt for a room with a clawfooted soaking tub or an outdoor cedar tub) or the just-opened Kenoza Hall, from the area’s esteemed Foster Supply Hospitality. The 55-acre property can be traced back to the 1800s.

Saratoga Springs

If you thought the only thing to do in Saratoga Springs was going to the racetrack, think again. This quaint city about four hours north of New York City is having a bit of a renaissance, with excellent new hotels and the Upper Hudson Valley Wine Trail, made of an ever-growing roster of family-run vineyards and wineries. Some of them, such as Victory View Vineyard, are open for socially distant outdoor tastings. And if you visit between mid-September and early October, you might even catch the harvesting action. From here, you can easily explore scenic Lake George and the high peaks of the Adirondacks.

The Brentwood Hotel, which opened in 2016 in a revamped motor lodge, was a front-runner on the scene. Designed by Brooklyn-based Studio Tack, the 12-room boutique hotel features equestrian motifs inspired by its location just steps from the racecourse. Joining it is the historic Adelphi Hotel, which emerged from a top-to-bottom renovation in 2017 (even if you’re not a guest, be sure to elbow up to Morrissey’s, a clubby bar named for the yarn-spinning sportsman who brought horse racing to town) and the Downtowner, by Massachusetts-based Lark Hotels, which delivers punchy pops of color to the vintage motel backdrop.

The Berkshires

The Berkshires. (Photo by DenisTangneyJr/Getty Images)
The Berkshires. (Photo by DenisTangneyJr/Getty Images)

The secret’s out about this mountainous region in western Massachusetts. Equidistant from New York City and Boston, the Berkshires make for a perfect fall getaway complete with excellent hiking, world-class culture and great places to spend the night. Recent developments have made the area even more appealing for a weekend trip. Housed in a complex of 19th-century mill buildings in North Adams, MASS MoCA (the Massachusetts Museum of Contemporary Art) has long been a pilgrimage site for art lovers, and it has reopened to visitors. Don’t miss Sol LeWitt’s staggering wall drawings, a cornerstone of the museum since they were installed in 2008. The area is also home to the Norman Rockwell Museum (timed tickets required) and The Mount, Edith Wharton’s mansion in Lenox.

There are two exciting new places to stay in the Berkshires too, both Hyatt properties occupying the same estate. Miraval Berkshires is the third iteration of the wellness-focused chain. Guests can try horseback riding at Meadowview Stables, classes on beekeeping, hiking in the adjacent forest and treatments at the 29,000-square-foot Life in Balance spa experience. A free night will cost you 45,000 points, plus an additional 20,000 per night for an additional guest in your room.

Travelers can also bed down at the Wyndhurst Manor & Club, a Destination Hotels property occupying a Gilded Age mansion and cottage. The complex has elegant rooms, an outdoor pool, an 18-hole golf course and a fitness center. There are also two restaurants, including a tavern serving breakfast, lunch and dinner and the upscale 1894 Fireside Bistro serving lunch and dinner. Standard Rooms start at 25,000 World of Hyatt points per night.

The Hudson Valley

When it comes to an easy weekend escape from New York City, it would be hard to beat the Hudson Valley. The charming town of Hudson is just two hours away on Amtrak and about 2.5 hours by car. You can easily post up at the laid-back Rivertown Lodge, the food-focused Wm Farmer & Sons or the Wick: a relatively new Tribute Portfolio Hotel that just opened in a reborn 19th-century candle and soap making factory in town (from 25,000 points per night). There’s also the just-opened The Maker Hotel, which is currently in a soft summer opening. Located downtown, the intimate 11-room property is spread across three historical buildings.

For a more pastoral setting, head to Amenia and check into Troutbeck — an inn on a historic estate that once played host to Mark Twain, Henry David Thoreau and Teddy Roosevelt. Though it’s not currently accepting reservations, don’t forget about Collective Hudson Valley, a glamping site on the grounds of Liberty Farms, where you can overnight in a luxury tent. Either way, be sure to go sailing on the Hudson, enjoy leisurely hikes and go apple picking. This is fall in New York state, after all.

Central Vermont

Photo by DenisTangneyJr / Getty Images.
Photo by DenisTangneyJr / Getty Images.

At about five hours from New York City and under three from Boston, central Vermont’s bucolic mountain landscapes and small-town charm makes it the perfect destination for an autumn getaway. The entire state has a population of around 624,000, so you’ll find that even the capital of Montpelier feels like the kind of place where everyone knows each other’s name.

Situated in the heart of Woodstock, the historic Woodstock Inn & Resort — established by Laurence and Mary Rockefeller — recently emerged from a $16 million renovation, updating the Federalist-style building and its 142 rooms and suites. You can dine on farm-to-table fare at the Red Barns and indulge in a spa treatment at the 10,000-square-foot spa. In nearby Barnard, discover the all-inclusive Relais & Châteaux property Twin Farms — a collection of beautifully appointed, art-filled cabins spread across a 300-acre estate. Here, you can admire the changing leaves on the grounds, soak in the Japanese-style furo and go canoeing or fly fishing on the property’s pond.

Additional reporting by Melanie Lieberman. 

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