5 Perfect New England Foliage Day Trips from New York City

New York City is hardly short on green spaces, but when autumn rolls around, it may take more than a walk in the park to satisfy the most ardent leaf peepers. As the days turn crisp and cool and the foliage colors brighten, New England’s siren song is hard to resist. And why should you? There are plenty of great destinations in southern New England that can be reached in just a few hours by car from Manhattan. Here are some of our favorite New England foliage day trips from NYC.

5 Perfect New England Foliage Day Trips from NYC

Kent, CT

Miles from NYC: About 80

Approximate driving time: 1 hour, 45 minutes

Nestled along the New York border in Connecticut’s rural Litchfield Hills, Kent offers picture-perfect views across the Harlem Valley to the Taconic and Catskill mountains, with diverse dining options, outdoor adventures, and a thriving art scene. Head to Macedonia Brook State Park for a trek up Cobble Mountain to enjoy expansive views of the Catskills and Taconics, or try the quarter-mile Kent Falls Trail at Kent Falls State Park, which takes you over a covered bridge to the namesake 250-foot cascade. Afterward, you can wet your whistle with a brew at Kent Falls Brewing Co., where the hops are grown on surrounding land that’s been used in agriculture for more than 250 years, or treat yourself to the hand-dipped truffles and small-batch coffees at Kent Coffee & Chocolate Co. 

East Haddam, CT

Miles from NYC: About 120

Approximate driving time: 2 hours, 20 minutes

Water brings a little something extra to autumn in East Haddam, where you can fall under the spell of reflections in the Connecticut River or thrill to the cascading brooks and waterfalls of Devil’s Hopyard State Park. Wildlife watchers will want to book a riverboat cruise to enjoy nature’s show and possibly spy eagles soaring overhead. See festive foliage reflected in the Connecticut River from atop Gillette Castle State Park, which straddles East Haddam and neighboring Lyme. The medieval-looking fortress, built in 1919, is closed after Labor Day but the 184-acre estate’s trails are open year-round. For dining options, look across the river to Chester, where the Pattaconk 1850 Bar & Grille, festooned with flags, celebrates “the largest beer selection in the River Valley.” Can’t choose between River Tavern’s crispy tofu and Otto’s lamb meatball/ricotta/pecorino/mint pizza pie? No worries, it’s the same owner.

Great Barrington, MA

Miles from NYC: About 120

Approximate driving time: 2 hours, 30 minutes

The Berkshires town of Great Barrington is a delight for hikers and foodies alike. Those looking to stretch their legs should head to Monument Mountain, a gorgeous Trustees property crowned by a 1,642-foot peak. Its moderate 2.8-mile loop trail is very popular during the summer months, so visiting in fall can be a great escape from the typical traffic. Expect a wonderful view of the foliage-tinged Housatonic River Valley and the southern Berkshires at the summit. Back down in town, give thanks for the eat-local, farm-forward community of dedicated, food-savvy year-rounders that has spawned a top-notch collection of restaurants, including Bizen, The Prairie Whale, and GB Eats, to name a few. And don’t miss a stop at Guido’s Fresh Marketplace, the kind of green/gourmet/everyday supermarket that every town deserves, but few have.

Sturbridge, MA

Miles from NYC: About 152

Driving time: Approximately 2 hours, 40 minutes

History runs deep in the central Massachusetts town of Sturbridge. Settled in 1729 and officially incorporated nine years later, Sturbridge is best known today for Old Sturbridge Village, a living history destination that re-creates what New England life was like in the 18th and 19th centuries. Visitors with a hankering for more things past can lose themselves for hours browsing in Sturbridge Antique Shops, where more than 80 dealers from all over New England fill two floors with antiques and vintage collectibles. When it’s time for a break, you can find local suds at Rapscallion Brewery, Altruist Brewing Company, and Homefield Brewing — plus just up the road is Tree House Brewing Company, which in 2020 was ranked the fifth best brewer in the world by the website RateBeer. For a little climb and a scenic vista across the autumn landscape, head to Wells State Park and climb to Carpenter Rocks, a granite outcrop that puts you above the trees. And don’t forget to grab some apples for the drive home at 150-acre Hyland Orchard, a third-generation farm, where you can pick your own.

Williamstown, MA

Miles from NYC: About 162

Approximate driving time: 3 hours

The ultimate college town, sheltered in the arms of Massachusetts’ highest mountain — Mount Greylock, in nearby Adams — Williamstown offers a mix of eclectic architecture and inviting quads that can’t help but inspire lofty thoughts. You can sidestep the exertion of summiting Greylock while still reaping its visual rewards when you stride up the 1.9-mile-long unpaved Sperry Road to the Stony Ledge outlook, which offers a vertiginous 1,400-foot view into the Hopper, a steep-sided bowl notable for old-growth woods, with a majestic panorama of the Bay State’s highest peaks. For a more in-town destination, it’s a best-kept secret that the Clark Art Institute’s 140-acre “backyard” is laced with walking trails open free to the public; hike up Stone Hill for bird’s-eye views. Of course, you won’t want to miss the Clark’s actual art collection either: Wander into its galleries to view an impressive collection of Impressionism, with canvases by Monet, Manet, Degas, Renoir, and Cezanne and an entire room devoted to American master Winslow Homer.

Do you have any favorite New England foliage day trips from NYC? Let us know!

SEE MORE:

10 Places to Visit in New England in Fall

Prettiest Fall Foliage Villages in Vermont

The Ultimate New England Fall Foliage Road Trip

PRINT