The Ultimate Fall New England Bucket List for 2023

48 unforgettable activities to do this season, from spectacular adventures (hot-air ballooning, skydiving) to extravagant indulgences (luxe spa days, casino trips) to simpler pleasures (sunrise canoeing, ceramics).

Trail under Mount Kineo face. / Photo by Posrow/Getty Images

Is there anything better than autumn in New England? The sun is still warm and bright, the leaves are radiant, and the humidity has finally dipped below “pump the air conditioning” percent. But as much as we love the season, it can get a little drab visiting the same old pumpkin patches and orchards every year. That’s why we’ve put together this guide to 48 unforgettable fall things to do, from hot-air ballooning and skydiving to simply rowing a canoe at sunrise in the wilds of Maine. Check off as many as you can this year, then keep the list handy for next October—you’ll want to try everything at least once.

☑ Leaf peep by helicopter.

Autumn leaves are equally stunning in the city and the country. Why not enjoy both locations in the same weekend? With a fall package from the Kimpton Marlowe Hotel, you’ll stay at the hotel in Cambridge for a night, then hop on a helicopter and fly over to the Kimpton Taconic Hotel in Manchester, Vermont, glimpsing trees covered in reds, yellows, and oranges from up high along the way. After two nights of fall adventures, you’ll fly back to Boston for another VIP foliage journey in the sky.

Photo by Bob_Bosewell/Getty Images

☑ Pick up a new hobby.


Craft a new bowl for cold-weather soups or a mug for a steaming cuppa at Belfast Clay Studio in Belfast, Maine. The Happy Hour “try-day” for beginners includes a demonstration of wheel-throwing before participants shape their own vessel out of the mud. Included is the firing and glazing of your creation, as well as wine and light snacks—it is happy hour, after all.


Find a new way to appreciate the morning light streaming through your windows with a class at Fulcrum Stained Glass in Warwick, Rhode Island. Snag a spot in the “Make and Take” workshop for beginners: Instructor Renee Metro will cut and grind the glass pieces ahead of time; you’ll do the work of adhering and soldering what you make, whether it’s a suncatcher or a small accessory.


They don’t make things like they used to anymore…unless you’re making it yourself. The week-long course in beginner furniture making or basic carpentry at Yestermorrow in Waitsfield, Vermont, will teach you the ins and outs of woodworking—including how to build a coffee table, a console table, or a dining table.

Photo by Enzo Figueres/Getty Images

☑ Chase a waterfall.

Mosquitos, be gone. Enjoy these cooling waterfalls during cooler temps.

Crawford Notch, New Hampshire

Hiking to Arethusa Falls in the White Mountains begins with a few waterfall appetizers. Take the Bemis Brook Trail to glimpse Bemis Brook Falls early on in the hike—it’s a much smaller take on the spectacle you’re about to see—and then Coliseum Falls, another medium-size cascade. Forge uphill to see the main event in all of its 160-foot glory.

Forks, Maine

You’ll know you’re close to this waterfall—one of the Pine Tree State’s tallest—when you hear a whooshing sound along the trail. It’s no wonder you can hear it before you see it: The vertical drop clocks in at a whopping 90 feet. Feeling adventurous? Daredevils can visit the base of the falls via an extremely steep path: Sturdy shoes and climbing ability required.

Granby, Connecticut

This off-the-beaten-path adventure used to be a bit challenging to navigate, but thanks to the addition of new stone steps and wooden fencing along the path, as well as a viewing platform, it’s now easier than ever to watch the water flow down a series of mossy rocks.

Photo by Kirkikis/Getty Images

☑ (Try to) visit every state park in Massachusetts.

It’d be nearly impossible to knock out all of Massachusetts’ 100-plus state parks before the end of the month, but if you start now, you could put a pretty big dent in your list by springtime. (And that’s not even counting our national wildlife refuges, national historic sites, and 36 state forests!) Begin with a challenge this month by scaling the peak at Mount Greylock State Reservation (not far from North Adams), the highest point in Massachusetts.

The Norumbega. / Photo by Douglas Merriam

☑ Stay somewhere new.

And enjoy these unforgettable long-weekend itineraries while you’re at it.

Camden, Maine

Friday: Channel your inner bookworm in the Library Suite at the Norumbega, which was recently renovated by its new owners. Select a title from the suite’s upper-level shelves and unwind after the long day in a plush velvet armchair.

Saturday: After a morning spent scaling Mount Battie, head downtown for some shopping in the afternoon. Stop in Hundred Acres for one-of-a-kind housewares, Liberty Graphics for a ’70s-style nature-themed T-shirt, and Goods for small-batch pantry items and a glass of orange wine.

Sunday: Don’t drive home without stopping at the Alna Store in Alna, Maine, for lunch. The small market and restaurant serves elevated dishes, cocktails, and dessert just a quick detour off Route 1.

Blind Tiger. / Photo by Matt Kisiday

Burlington, Vermont

Friday: Set your bags down in this gorgeous, just-opened B & B inside a historical 1880s mansion, then head to the back deck to survey the property’s stunning gardens. Sipping on a pét-nat from nearby Dedalus Wine Shop is optional but encouraged.

Saturday: Rent a bike from Local Motion to pedal along the Island Line Trail, which eventually cuts across Lake Champlain via the scenic Colchester Causeway, letting you bike with water on both sides of your handlebars.

Sunday: Enjoy a leisurely breakfast in the inn’s checkerboard-floored solarium, then stop for pastries to take home at August First before hitting the road.

Lumen Nature Retreat. / Courtesy photo

Woodstock, New Hampshire

Friday: Grab some firewood from the basecamp before finding your site at this brand-new glampground. You’ll want to luxuriate in one of the hygge cabins, which overlook a rushing brook and come with fireplaces.

Saturday: Start your Franconia Notch State Park adventure at the Gilman Visitor Center at Flume Gorge, where you can learn the history of the mountains surrounding you. Then take the 2-mile loop around the gorge to get up close and personal with whooshing waterfalls and sparkling natural pools.

Sunday: Fuel up with lunch at Schilling Beer Co. in Littleton, a craft brewery offering European-style lagers and ales. Sip on Schlaumeier, a Bavarian wheat ale with notes of banana and clove, along with a side of bratwurst and sauerkraut in the brewpub. Then grab a four-pack from the tasting room to take home.

North Adams

Friday: Fuel your Berkshires weekend with some espresso and smoked-salmon toast from the Break Room at the new Greylock Works campus, a former mill turned mixed-use cultural space.

Saturday: Enjoy the art studios off the lobby at the newly opened Hotel Downstreet. Then take a short stroll to North Adams’s pride and joy: Mass MoCA. Don’t miss EJ Hill’s first solo museum show, “Brake Run Helix,” inspired by the experience of riding a roller coaster.

Sunday: Just beyond Mass MoCA’s front door is Casita, a new restaurant and bar that highlights Mexican cooking. Whatever you do, don’t leave without trying the yucca fries with chipotle mayo.

Courtesy photo

☑ Drive an exotic car.

Cruising down the Kancamagus Highway in your Land Rover is undoubtedly a transcendent experience during the fall. But what if you kicked things up a notch and got behind the wheel of a Ferrari 488 Spider instead? Your leaf-peeping cred will go through the (nonexistent) roof of this convertible, which can be delivered to your hotel’s door by Gotham Dream Cars. They’ll pick it up when your meandering foliage drive is complete.

☑ Rent out a movie theater.

Sure, movie nights at home are fun, but nothing beats seeing your favorite flick on the big screen. To really go all out this fall, round up your best friends for a watch party in the grandeur of the New England Aquarium’s Simons Theater, which will play any film you can score on DVD or Blu-Ray. And forget plain old popcorn: You can also host a small gathering in the theater’s lobby, with add-ons including a poke bar, a sushi bar, a churro bar, and a hot-chocolate station.

AegeanBlue/Getty Images

☑ Camp off-grid.

Pitch a tent miles from the camping masses and savor the sweet solitude.

Cutler, Maine

Best suited for experienced hikers, this trip gives you all the rocky splendor of Acadia with none of the crowds, plus the sound of crashing waves to lull you to sleep at night. To get to one of the five designated campsites along Maine’s Bold Coast, you’ll need to backpack roughly 3 to 5 miles along the Coastal Trail. Set out for the sites at Fairy Head, which are furthest from the parking lot and offer views of the ocean from your tent.

Errol, New Hampshire

Sure, you could pitch a tent with the rubes at the more traditional campground near the southern shores of Umbagog Lake, but for a quiet night in nature, your best bet is to seek out one of the 33 remote sites peppered across the state park. There are also four remote cabins to rent, but they’re on an island in the lake, meaning they’re only accessible by boat. Rent a canoe or kayak from the park, and off you go.

Underhill, Vermont

Looking at mountains is nice, but sleeping on one is even better. Situated on the western slope of Mount Mansfield, the highest peak in the state of Vermont, Underhill State Park offers lofty hiking and camping at 2,000 feet above sea level. You’ll have to walk about three-quarters of a mile from the park’s ranger station to get to the more secluded upper camp area, where there are seven lean-tos and two tent sites for groups.

☑ Go on an inn crawl.

You don’t need to endure overnight hiking trips—and the back strain and bad hair days that come along with them—to log a rewarding journey across New England. The self-guided Vermont Inn-to-Inn Walking Tour lets you stroll country backroads at your leisure, then come back to a comfortable bed at the end of the day. Here’s how it works: You pick an inn along the tour’s 40-mile circular route, enjoy dinner there, and then set out in the morning for your next inn, strolling between 7 and 13 miles to get there. Your innkeeper sends your bags on to your next destination, so you’re not bogged down by heavy stuff. Sounds like our kind of hike.

Courtesy photo

☑ Hop on a hot-air balloon.

If you’re afraid of heights (or fire, or wide-open spaces), you might want to stop reading. But if you’ve always dreamed of becoming one with the breeze during a scenic hot-air balloon ride, you needn’t travel farther than Salem, New Hampshire. There, A & A Balloon Rides will take you high into the sky (to the tune of 500 to 2,000 feet!) to gently float over rolling hills, lakes, and rivers. After the flight, you’ll come down from the journey—literally and metaphorically—with cheese, crackers, and champagne.

☑ Swing from trees, VIP-style.

Swinging from the trees should be on your bucket list no matter when you do it. But things get downright magical during weekend “night climbing” events at Treetop Adventures, a high ropes obstacle course in Canton. Kick things up a notch by booking the VIP experience, during which you’ll not only climb among string lights, glow sticks, music, and performers under the stars but also get your own designated hangout space.

Photo by Dushlik/Getty Images

☑ Hire a private plane.

The five-hour drive to Bar Harbor can feel endless when autumn adventures await. So why not make the journey part of the adventure? By chartering an eight-seat Pilatus PC-12 turboprop with Air Charter Advisors, you can be there in less than 60 minutes. A chauffeur service picks you up at your home and drives you right to the side of the aircraft at either Hanscom Field or Logan. On the plane, you’ll kick back in leather seats with a side of surf and turf (a seafood tower and filet mignon, anyone?) before you’re whisked home a few days later without having to lift a finger.

Photo by Jonathan Blackham/Getty Images

☑ Conquer a mountain on two wheels.

What goes up must come down—via mountain bike, that is.

Northfield, New Hampshire

Mountain-biking beginners bold enough to start with a downhill descent should register for Highland’s “Find Your Ride” program, which includes a bike rental, a full-face helmet, and a quick intro lesson. You’ll take the lift up to the top, and bike down a beginner-friendly trail with a guide.

Killington, Vermont

Choose from one of three high-speed lifts to get to the summit at Killington Bike Park, where you’ll cruise downward over rocks and roots—generously aided by gravity, of course. Dare to register for a group lesson with a gang of fellow biking novices or go it alone with a private session.

Lincoln, New Hampshire

Aptly named the “Kancamagus 8” after the nearby scenic highway, the lift here brings you to the top of the trails in less than 6 minutes. From there, you can bike down 11 miles spanning 1,000 vertical feet. As you round each bend and speed through straightaways, you’ll glimpse views of the surrounding mountains through the trees.

☑ Watch the sun rise at a lake.

Ready to watch the sun poke its head up from the horizon while gently paddling one of Maine’s most scenic bodies of water? You can make that a reality on Moosehead Lake this fall. All you have to do is rent a canoe from Moosehead Area Rentals (they’ll deliver it to you the night before!), set off from the Rockwood Boat Launch before dawn, and then leisurely make your way across part of Moosehead Lake to Mount Kineo while the sky erupts in pinks and oranges. If you’ve shaken off the sleepiness, opt for a hike to the top of Mount Kineo for more jaw-dropping vistas before rowing back to the opposite shore for a hearty breakfast.

Courtesy photo

☑ Skydive.

Is inching a few miles per hour over the speed limit on the Mass. Pike not satisfying your need for speed? Jumping out of a plane over the great state of Maine should do the trick. Opt for Skydive New England’s freefall tandem dive with an instructor to feel the wind in your hair (and your jowls)—and if you want something to commemorate your feat of bravery, add on the “Rockstar” video package, during which a professional videographer will dive with you to capture your big moment from a bird’s-eye view.

☑ Lean into shoulder season on the Cape.

A trip with no traffic calls for celebration. Do something splashy, like…

Photo via Chatham Bars Inn

Drop $50,000 on the craziest Cape escape in existence.

A new over-the-top package from the Chatham Bars Inn invites two people to go all out for five nights in an oceanfront suite. Perks include a biplane tour of the Cape, an off-roading adventure in a Lexus GX460, a day trip by boat to Nantucket, a private clambake on the beach, unlimited spa treatments, a fishing excursion, a tasting in the inn’s wine cellar, and more.

Photo via Atoss/Getty Images

Stroll beside a cranberry bog with just the gulls as your witness.

Annie’s Crannies’ owner Annie Walker doesn’t advertise guided tours—instead, she hopes you’ll discover her little farm in Dennis while wandering off the beaten path. “We’re pretty low-key here,” says Walker, who gives the tours herself. On weekends in October, she’ll show you around the bogs and inside her barn, where antique machinery sorts the berries before your eyes.

Photo by Serhii Tychynskyi/Getty Images

Enjoy oysters straight from the source.

With a private or group tour of Cottage City Oyster Farm on Martha’s Vineyard, you’re invited to sample the delights of the open sea, on the open sea. Board the Leeward to hear the history of the business and how, exactly, oyster-growing works. Then watch as shuckers turn the boat into a loaded floating raw bar so you can get down to business of your own.

The Bodhi Spa. / Photo by Maaike Bernstrom

☑ Take a spa day.

Newport, Rhode Island

WHY GO: To dip your toe into the world of hydrotherapy.

TREATMENT TO TRY: In the “Water Journey,” a treatment likened to a Japanese bathhouse, you’re guided through a series of water-based experiences: A hot tub to start, a steam room, then a cold plunge, followed by an infrared sauna, another cold plunge, another dip into a hot mineral pool, and one final cold plunge. The result is equal parts
therapeutic and rejuvenating.

The Tree Spa at Hidden Pond. / Courtesy photo

Kennebunkport, Maine

WHY GO: For the treehouse treatment rooms, of course: Built in a stand of birches, each draws inspiration from the nature that surrounds the place.

TREATMENT TO TRY: Tap into your inner camper by selecting the “Circadia S’mores Body Treatment.” Meant to reduce inflammation, a soothing concoction made with cocoa not only smells delicious but also repairs dehydrated skin. A marshmallow-whip hydrating mask seals in the moisture.

Wolfeboro, New Hampshire

WHY GO: Ever wake up from a dream where you felt weightless? You can make that dream a reality in the Northeast’s largest float-therapy room.

TREATMENT TO TRY: Opt for the single or double Float Room Package before settling into the “float cabin,” which features a pool of body-temperature water and 1,000 pounds of Epsom salt. Then simply float, either in complete darkness and silence or under soft lighting resembling a night sky. You can practically feel the aches and pains melting away.

Photo by Visoot Uthairam/Getty Images

☑ Run in a road race.


Bar Harbor, Maine
8 a.m., October 15

It’s been dubbed America’s most scenic road race, and for good reason: You’ll traverse fishing villages, verdant fields, and more while passing mountains, lakes, and the mighty Atlantic. But the highlight on the journey from Bar Harbor to Southwest Harbor might be running beside Somes Sound, the only fjord on the Eastern Seaboard.


8:10 a.m., October 21

Sprint like something’s hounding you along this 6.66-mile course, where the majority of runners dress like horned demons as they pass by the House of the Seven Gables, the Salem Common, and the ghosts of runners past.


Franconia, New Hampshire
9 a.m., October 28

Starting from the base of Cannon Mountain, this half marathon meanders past the mirror-like waters of Echo Lake, the Old Man of the Mountain viewing site, the massive Boise Rock, and other White Mountains landmarks. The race culminates with a sizzling cookout on the deck of the mountain’s Peabody Lodge.

Photo by Jake Snyder/Red Skies Photography

Test New England’s top beers.

Waitsfield, Vermont

WHY GO: It’s easy to pass a whole afternoon enjoying a flight or two of the brewery’s myriad IPAs—including the signature Sip of Sunshine—not far from Waitsfield’s iconic covered bridge.

FALL MUST-ORDER: Fill your pint glass with the Mad River Maple ale, a rich, slightly sweet beer brewed with pure Vermont maple syrup.

Charlton and other locations

WHY GO: To stock up on the good stuff—a generously sized crate of Tree House cans—after sipping on a draft pour.

FALL MUST-ORDER: Hold on to Sunshine is a peanut butter–chocolate milk stout that’s meant to be enjoyed as autumn arrives.

Greensboro Bend, Vermont

WHY GO: To bask in this cult-favorite brewery’s beer meadow, where picnic tables dot a verdant expanse just beyond the taproom.

FALL MUST-ORDER: There is no wrong order here, but Song of Autumn is a seasonally appropriate choice—the red IPA matches the surrounding foliage and is brewed with Vermont-grown hops to boot.

Salem, Connecticut

WHY GO: Tucked away on a curving country road, this top-notch brewery offers a quiet escape from the kinds of places that have lines snaking out the door.

FALL MUST-ORDER: Get in the Oktoberfest spirit with a pint of Rays, a Bavarian-style weissbier, or a Helmhold, a dry Munich-style dunkel.

Exeter, Rhode Island

WHY GO: For a farm-to-pint experience that also offers snacks from local food trucks and live music.

FALL MUST-ORDER: A pumpkin stout called Blackjack is a fan favorite, but you’ll need to save room for one of Tilted’s highest-rated beers of all time: The Other One, a dry-hopped double IPA.

Photo by Josh Ross/Getty Images

☑ Try fly-fishing.

Fly-fishing isn’t just for pro anglers—it’s for anyone who wants an extra reason to ogle the reflection of orange and red leaves on the water. Try it at the newly reopened Hermitage Inn in West Dover, Vermont, a getaway that looks like it’s been plucked from an idyllic storybook. Guests can book a clinic with an expert fly-fishing guide and learn the ropes in the property’s private trout pond. Rods, nets, flies, and all the gear you’ll need is provided—just bring yourself and a positive attitude.

☑ Go green for a day in Maine.

Photo via FlamingPumpkin/Getty Images

The ultimate cannabis-forward fall itinerary in Portland.

MORNING: Pull up a chair to one of the very chill café tables at Higher Grounds Coffee, a dispensary-slash-coffee shop. Locally roasted brews are infused with CBD oil for a relaxing way to start the day.

NOON: A museum…about cannabis? Yes, it’s a thing, and it’s worth checking out. With locations in Boston and Portland, Core Social Justice Cannabis Museum‘s exhibits examine the inequities of U.S. drug policy over the years. Bonus: Seed, the related dispensary next door, is fully stocked with edibles, tinctures, and more.

NIGHT: Somehow, the nautical views at Portland Head Light are even prettier under a haze—so sip on a THC-infused mango seltzer from Seed at your hotel, and then head straight to Fort Williams Park on the waterfront.

The Topgolf Swing Suite at MGM Springfield. / Courtesy photo

Act like a high roller.


Morning: Gambling is more fun after carb-loading at Bill’s Diner at South End Market, MGM’s food hall. A revamped breakfast menu offers rib-sticking fare such as “better-than-mom’s” pancakes, waffles, and breakfast sandwiches.

Noon: Plan for an early afternoon tee time in the Topgolf Swing Suite. Practice your swing, hit a couple of virtual drives, and then kick back in a stately leather armchair while watching your pals do the same.

Night: After dinner at the Chandler Steakhouse and a blackjack sesh, catch a show at Roar! Comedy Club, located inside MGM’s castle-like refurbished armory. Andrea Jin is among the stars coming to the stage in October.

Mémoire at Encore Boston Harbor / Photo via Big Night


Morning: Before hitting the slots, make an appointment for the Spa’s “Good Luck Ritual.” Meant to bestow prosperity, the full-body massage is paired with a hand-and-foot scrub.

Noon: You’ll need some serious fuel for the night ahead. Opt for brunch at the Garden Café: Lobster Benedict washed down with a glass of green juice is a balanced meal, right?

Night: Tonight’s the night you finally let loose in Mémoire, Encore’s Vegas-style club. After a little caviar at Rare Steakhouse, reserve a VIP table so you can indulge in bottle service before losing yourself on the dance floor under colorful lights.


Morning: Kick off your high hopes for the day with an invigorating hike along the casino’s Pequot Trails—one of which ascends nearly 500 feet and offers commanding views of Block Island Sound.

Noon: Place live bets on your favorite teams while tucking into stadium-style plates like fried pickles and loaded nachos at the recently opened 12,000-square-foot, two-story
DraftKings Sportsbook.

Night: After hitting the roulette table, stop by Red Lantern for some ultrafresh maki and nigiri. Or watch the action in the open kitchen at the casino’s newest restaurant, Gordon Ramsay’s Hell’s Kitchen. Classic dishes from the eponymous show grace the menu, including beef Wellington and sticky toffee pudding.

Photo via Common Man Roadside Market

☑ Savor a pumpkin dessert.


WHERE: Common Man Roadside Donut Shop in Hooksett, New Hampshire, at the I-93 North rest stop and at the new location on the I-93 South rest stop.

WHY: A rest stop doesn’t seem like the place you’d find a destination-worthy dessert, but trust us: This one is worth making calculated stops for on your way to (and from) leaf-peeping land, thanks to pillowy pumpkin doughnuts drizzled with maple glaze and stuffed with frosting.


WHERE: Gross Confection Bar in Portland, Maine.

WHY: The delicate mousse is like a PSL on steroids, topped with bits of pumpkin cake and blondies, plus chocolate pearls and cider gelée.


WHERE: Elmwood Pastry Shop in West Hartford, Connecticut.

WHY: Stuffed generously with lots of golden caramel and finished with a cream cheese swirl, this gooey mixture of pumpkin-flavored cake is meant to be shared, though you’ll probably want to keep it all to yourself.

First published in the print edition of the October 2023 issue with the headline, “The Ultimate Fall Bucket List.”

Photo illustration by Benjamen Purvis.