12 Outdoorsy New England Adventures Open Through Autumn

There’s a stampede every September as folks clammer for their first sip of pumpkin spice lattes and hot ciders. This is especially true in New England—what with all our orchards and farms. My particular brand of seasonal nerdery includes all forms of autumnal shenanigans, but the leaves are still green. So, while I wait for the annual New England foliage show, I’m enjoying the fact that many of the most popular spots are quieter now that the summer crowds have thinned. Plus, there’s still time to enjoy these outdoor adventures—before Old Man Winter shows up.

Golf in the Majestic White Mountains—With a Llama Caddy

Whitefield, New Hampshire

I don’t golf per se, but New Hampshire’s Mountain View Grand Resort & Spa offers a Llama Tee Time Trek golf package, so that’s (obviously) the only nudge I need. Llamas from the resort’s farm caddy for guests—which is awesome on its own—but they also throw in unlimited drinks and snacks (for you, not the llama). Of course, your llama caddy is accompanied by a professional handler, but your own your own for trying to tamp down your childlike glee.

Credit: Guest House Creative

Ride Horses and Drink Local Hooch in Your Helicopter Cottage

Morris, Connecticut

The quiet splendor of Connecticut’s Litchfield Hills should also be on your Autumn in New England list. The folks at Winvian have mastered the art of elegant whimsy, and their cottages are—in a word—bonkers. I stayed in a barn cabin with a screened porch, steam shower, hot tub, and a helicopter. An actual helicopter where I watched television and sipped local hooch. Their many experiences include horseback riding, forest bathing, and Tibetan sound therapy.

Bike to Kennebunkport’s Goose Rocks Beach

Kennebunkport, Maine

Sit on the front porch of the Cape Arundel Inn & Resort with your beverage of choice and watch the boats. That’s all you really need because it’s so deeply relaxing and idyllic. Then again, if you’re feeling cheeky, grab a complimentary bike and head out on a 7.4-mile ride to Goose Rocks Beach. Though some Kennebunkport shops are seasonal, there’s still plenty to see in the off-season. Later, have dinner at the hotel’s Ocean Restaurant; they use a pistachio crust on the cheesecake (chef’s kiss!).

Drive a Gnarly Land Rover Course and Test Your Pinball Skills

Manchester, Vermont

Is there a greater joy than navigating a gnarly Land Rover course with two or maybe three wheels on the ground? The Kimpton Taconic Hotel offers a Land Rover Driving Experience, where guests head into the woods with a certified instructor for an off-road driving lesson that is equal parts educative and adrenaline-inducing. While in town, get a bird’s eye view of the fall foliage on Mount Equinox Skyline Drive and stop by Pastime Pinball to play pinball machines from throughout the history of the greatest game.

Sail an America’s Cup Winner in Newport

Newport, Rhode Island

Those looking to eschew Newport’s summer crowds can still have maritime adventures when fall rolls around. I sailed with America’s Cup Charters recently. They sail actual America’s Cup yachts, and I was giddy with anticipation as we boarded the Intrepid—1967 and ’70 winner of The America’s Cup. Exhilarating is just the beginning; it’s a grand New England adventure. Plus, I stayed at The Vanderbilt, which has a cozy Great Gatsby ambiance, and one of their Classic Car Tours—billed as a Croquet & Picnic Cruise—is pure autumn magic.

From Kayaking and Dancing to Beach Fires—Cape Cod awaits

Cape Cod, MA

Autumn on the Cape deliver the best of all things New England—the foliage, the coast, and a bit of adventure. On your way, make a stop in Sandwich and see the folks at Rideaway Adventures for some foliage-friendly kayaking. Afterward, sit for an al fresco meal at Pilot House, overlooking the water. From there, head to Provincetown for an autumn getaway at the historic Crown Anchor—famous for its next-level LGBTQ+ experience and a quick walk to Provincetown’s popular Tea Dances. Looking for the perfect oceanfront firepit? Check out the newly renovated Red Jacket Beach Resort in South Yarmouth.

Enjoy Private Access to an Observatory on Nantucket

Nantucket, Massachusetts

Fall in New England usually has everyone looking up at the leaves, but guests at Greydon House are looking up at the stars—at Maria Mitchell Association’s Loines Observatory. Named for the first female astronomer in the United States who discovered the comet “1847 VI” while stargazing on the island in the 19th century, the Maria Mitchell Association offers hotel guests private access and one-on-one guided tours.

Credit: Daniel Schwartz

Rejuvenate with Beekeeping, Jam-Making Sessions, and EndlessTKTK

Lenox, Massachusetts

By early fall, you may need to rejuvenate. The serenity of Miraval Berkshires Resort & Spa provides an all-inclusive vibe and a robust yet mindful activities calendar. More tome than tally, the innumerable experiences range from a farmers’ market and jam-making session to beekeeping, outdoor meditations, and Twilight on the Farm, where guests are invited to help with garden and animal chores as the sun sets.

Summit Mount Washington in an Open-Air Roadster

New England and Beyond

Grab a pumpkin spice latte and cruise around New England in a three-wheeled, open-air roadster. Polaris Adventures offers six Slingshot rental options throughout New England—in Connecticut, New Hampshire, Rhode Island, and Maine. For the best autumn views in New England, I’m partial to the Mountain Washington Scenic Drive with its incredible views of the White Mountains. Cue the girls’ weekend and pair with the nearby Mountain View Grand Resort & Spa.

Test Your Mettle on The Racetrack

Lakeville, Connecticut

Though Lime Rock Park is open year-round, the 2024 seasons wraps up with MiataCon in October. Watching the races is a blast, but you can up the ante by getting out on the track yourself. Check the track calendar for programs like Autocross Lapping Day. Once you’ve taken one of these courses, you’re eligible to rent a track-ready car and test your mettle on the main Lime Rock Park circuit.

Ditch Your Car and Dabble in Art on Nantucket

Nantucket, Massachusetts

Ditch the car. That’s the Faraway Nantucket advice, and it’s totally doable given the hotel’s central location and proximity to the ferries and all the good stuff Nantucket is famous for. I adore the summer buzz of a coastal hotspot, but Nantucket and autumn go together like khakis and boat shoes. While there, maximize your al fresco time with an outdoor art class where you’ll learn pencil and pen techniques to sketch, journal, and capture little inspirations throughout the day.

Is There Anything Better Than Fly-Fishing in Maine?

Waterville, Maine

Fly-fishing on the Kennebec River awaits, and Lockwood Hotel’s Maine River Retreat makes a day of it. They get guests fueled up with pre-excursion fiddles from their restaurant, Front & Main. Then, off on a half-day adventure that caters to all levels, including absolute beginners. Fly-fishing brings together nature and the art and practice of patience, plus it’s a kick-ass way to enjoy the New England foliage. After the outing, another Front & Main meal rounds out the day.

Melanie Carden is a Boston-based travel and lifestyle writer.