5 Ultimate Fall Experiences in New England

New England’s charm spans all seasons, but it’s during fall when the region is most magical. Technicolor foliage blankets the land. Mild, sun-kissed days give way to crisp, starlit nights. Rich and varied harvests hold testament to this nexus of fertility. From late September to early November, there’s no place on Earth quite like it.

Here, we present five experiences for maximizing your New England fall and crafting an autumn to remember. Reserve your Tradewind flight by the seat on our daily shuttles from New York to Boston, Martha’s Vineyard, and Nantucket, or book your private charter to the airport of your choice.

1. Take a Leaf-Peeping Road Trip from Boston

All paths to New England’s multi-hued finest are easily reached from Boston. Head 116 miles west to access Massachusetts’s 63-mile Mohawk Trail. This route through the Berkshire Mountains is considered New England’s original scenic drive and follows a Native American trade route. Today, the trail’s some 50,000 acres of color-coated forest and parklands are dotted with charming, artisan shops specializing in everything from handmade quilts to house-made chocolates (try the chocolate caramel apples at Richardson’s Candy Kitchen).

Alternatively, from Boston travel 140 miles north to New Hampshire’s Kancamagus Highway, affectionately referred to as “The Kanc.” This scenic 35-mile stretch through White Mountain National Forest is the apex of New Hamsphire’s fall glory, bursting with blazing amalgams of orange, red, yellow, and green over the mountainous landscape. Unlike the Mohawk Trail, The Kanc lacks stores, gas stations, and restaurants, keeping the focus solely on nature.

2.  Wade through Massachusetts’ Cranberry Bogs

While we love New England’s prolific you-pick apple orchards and pumpkin patches, there’s no fall harvest experience as exciting—or photogenic—as “wet” cranberry farming. In the same vain as your favorite Ocean Spray commercials, you’ll wade through flooded cranberry bogs in rural Mass, raking in seas of the vitamin-rich red berries. Work on a farm for a day through the “Be the Grower Experience” at Mayflower Cranberries in Plympton, MA (45 minutes from Boston). Or, if manual labor isn’t your thing, observe the process of cranberry harvesting during the Nantucket Conservation Foundation’s Annual Cranberry Festival (Oct 7, 2017). Now in its 14th year, the festival dedicated to everything cranberries takes place at Milestone Cranberry Bog, one of the island’s two commercial cranberry farms.

3. Whale Watch in Stellwagen Bank National Marine Sanctuary

In summer and fall, the waters between Cape Ann and Cape Cod teem with thousands of migratory humpback, finback, and minke whales and several dolphin species, converging over a protected area known as Stellwagen Bank National Marine Sanctuary.  Summer is a busy time in Stellwagen, when it seems that boats outnumber whales. However, come early October, once the seafaring tourist hordes have left, you can really see why this region is cited as one of the top locales for whale watching in the world. See the highly intelligent leviathans in full force—without another boat in sight—on Boston Harbor Cruises, which runs whale watches until early November from New England’s Capital.  For visitors to Martha’s Vineyard, Hyannis Whale Watcher Cruises operates until late October from Barnstable Harbor on the Cape (and several hotels on the vineyard can arrange the whale watch as a day trip, including transport to Hyannis).

4. Channel Your Inner Tarzan and Spiderman in Stowe

Fall foliage is great at ground level, but it’s even better up in the trees. Thanks to a new aerial adventure course at Stowe Mountain Lodge in northern Vermont, gliding and swinging through the Vermont forest canopy is completely within reach. After a short training session, you’ll hook onto the cables that commence this exhilarating treetop adventure, going higher and deeper through a progressive series of obstacle courses woven through fall flora. Similar to skiing, the difficulty of each course is noted through a color–shape rating system. Prepare to test your balance skills, swing into sky high spider web nets like Tarzan (and then scale them like Spiderman), jump between floating planks, climb ropes, and zip line during this rip-roaring, often white-knuckled experience.

5. Take a Leaf-Peeping Road Trip from Stowe

In a state where maple-laced forest dominates, prepare for the brightest of fall colors around nearly every highway, country road, covered bridge, and white-steeple church. For maximum adventure, ditch the Google maps and just drive. You can’t make a wrong turn from Stowe—New England leaf-peeping is at its finest here. For something more organized, try a mini-road trip on the 11-mile Green Mountain Byway towards Waterbury (be sure to get some free samples at the Ben & Jerry’s factory along the way). Or for something more extensive, and to appreciate the diversity of Vermont’s fall flora, from Stowe continue on the Vermont 100 (beyond the Green Mountain Byway), all the way down the Green Mountains into Wilmington.