70 Ways to Soak Up New England This Fall

For the leaf peepers, the ghost hunters, the foodies, the shoppers, the sailors, the prepsters, and more: 70 ways to soak up New England this season

Litchfield

Discover scenes straight out of Gilmore Girls.

If you, like me, are anxiously awaiting the release of HBO’s Gilmore Girls documentary (filming now!), you can fill your proverbial cup with a visit to Stars Hollow’s very real stand-in: Litchfield County, Connecticut, a four-hour drive from Center City and show creator Amy Sherman-Palladino’s inspiration.

Make your home base ­Litchfield town’s version of the Dragonfly: Belden House & Mews (rooms from $455). It’s equal parts English countryside and quiet indulgence. Or check into The Abner (rooms from $291), a former county courthouse turned hotel that kept its judicial bones intact — its restaurant, The Courthouse, sits in the old courtroom.

Grab an iced coffee — Lorelai style — and a lavender shortbread cookie from Espresso 59 to enjoy under the dappled shade on the Litchfield Village Green. Then pop into I Ching Antiques for country and provincial heirlooms from Asia, and Milton Market for hand-framed original botanical paintings by local artist Caylin Jensen.

When it comes to cuisine, more than 1,000 working farms are scattered across the county, supplying kitchens with fresh bounty. Petraroia Deli’s cherry pepper, egg, and bacon sandwich gives Philly’s Middle Child sammies a run for their money. At dinner, Materia Ristorante’s risotto al pesto boasts a reduction made from langoustine heads simmered for a whopping 12 hours. And at Thorncrest Farm & Milk House Chocolates in Goshen, cows are raised on a strict diet of ample pastures and zero stress, for delicious honey cinnamon cream truffles.

Feel like getting out? Drive across the West Cornwall Covered Bridge and take the short but steep hike to the top of Kent Falls, its rushing water framed by turning leaves. For me, Arethusa Farm Foundation, back in Litchfield, was a highlight. The circa-1868 dairy farm, once owned by two former Manolo Blahnik execs and now a nonprofit dedicated to agricultural education, offers barn and pasture tours with enthusiastic (in a good way) executive director Bill Davenport, camps, and community programs such as flower arranging and wreath making. Cap things off with a fireside meal at 1850s GW Tavern in Washington Depot before heading home, windows down, crisp air on your skin and Mazzy Star on the radio.

Hit List: Hopkins Vineyard boasts autumnal views and wines with natural acidity due to its lakeside microclimate. Try the Vineyard Reserve white blend. — Claudia Gavin

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Rhode Island

Journey across the (entire!) state.

Maritime towns, a creative dining scene, 400 miles of coastline — all that, and Rhode Island is still the smallest of the 50 states. But that’s what makes it so easy to explore. (Plus, it’s just a five-and-a-half-hour train ride from 30th Street Station to Providence.) Post up at the riverfront LOOM Hotel (rooms from $100) in Warwick, then hit the road.

❶ Gather Glass Studio, Providence: Take a glass-blowing class, then get a scoop of caramel saltine frozen custard at Gather Cafe.

❷ Mémère’s, Providence: If French bistro classics imbued with New England flavors are your vibe, dine here.

❸ RISD Museum, Providence: Expect Egyptian artifacts, French impressionist paintings, and works by Philly-born artists including Alice Neel.

❹ Provi​dence Athenaeum, Providence: Edgar Allan Poe got dumped by his fiancée at this lending library.

❺ WaterFire, Providence: The full lighting of more than 80 bonfires along three rivers is set for October 17th.

❻ African American Museum of Rhode Island, Providence: It debuted earlier this year as the first museum in the state dedicated to the history of Black Rhode Islanders.

❼ Clouds Hill Museum, Warwick: This working Victorian manse has an Egyptian motif chandelier from Mitchell, Vance and Co, winners at the 1876 Centennial Exhibition in Philadelphia.

❽ Wickford Village, North Kingstown: Cedar-shingle houses, gift shops, and bayside res​taurants — like Tavern on the Sea — simply charm.

❾ Rosecliff, Newport: The Gilded Age mansion is known for its heart-shaped staircase, but don’t miss the “Revolution Reimagined” exhibit exploring the impact of the American Revolution on Newporters.

➓ Block Island: Take the high-speed ferry to this nature-filled isle and visit the Southeast Lighthouse along the Mohegan Bluffs for sweeping scenery. — Carla Shackleford

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Peep Show

Sightseeing adventures that put the basic scenic drive to shame

By train

Climb the Northeast’s highest peak on New Hampshire’s Mount Washington Cog Railway. The three-mile ride ends at a windswept summit; if it’s clear, you can see into five states and Canada.

By foot

In Maine’s Acadia National Park, scale the rung-and-ladder Beehive Loop for a pulse-pounding 1.4-mile climb, or take the 3.5-mile Gorham Mountain Loop for views sans the vertical drama.

By balloon

Lift off at sunrise in a Berkshire Balloons hot-air balloon, then float above Connecticut’s Farmington Valley and Litchfield Hills as patchwork farms and towns glow in the morning light.

By Rope

Near Stowe, Vermont, go inside the Green Mountains’ blazing fall canopy on ArborTrek’s 4,500 feet of zip lines, sky bridges, and tree rappels, soaring high above the forest floor.

By bike

Pedal six miles through Aquidneck Island, Rhode Island’s coastal woodlands, with Rail Explorers, whose four-wheeled bikes run on old railroad tracks. (Good for all ages!) — Regan Fletcher Stephens

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Boston

Experience an American tradition.

Philly is considered the birthplace of rowing in the U.S., but Boston, a 90-minute flight from PHL, is where you’ll find the world’s largest three-day rowing competition — the Head of the Charles Regatta, going strong every October since 1965. The race powers down the Charles River, between Boston and Cambridge, a picture-perfect route for a classically New England event. Be part of the epic tradition — this year’s takes place October 16th to 18th — by cheering on nearly 12,000 athletes. (Spectating is free.) The most thrilling places to watch: John W. Weeks Footbridge, where boats are forced to make a brutal 90-degree turn, and the finish line at Herter Park. (The latter is also the site of FALS Bar, with plenty of food and drink vendors.)

After the exhausting work of watching all that exercise, you can unwind at Guerlain Spa, the day spa inside Raffles hotel. I recommend the Boston Energy, a deep-tissue massage incorporating hot stones and oils from the French beauty brand. And stay at The Newbury (rooms from $611) in Back Bay, about four miles from the main course — a respite from the more than 325,000 expected race spectators.

Hit List: Mount Auburn Cemetery in Cambridge is the resting place for loads of famous Bostonians, but it also boasts some of the area’s most under-the-radar fall foliage. — Laura Brzyski

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Haunted History

Eerie alternatives to Salem during the October crush

Visit the Original Salem Village

The town of Salem gets all the attention, but what is now the Boston suburb of Danvers was once Salem Village, a rural farming community where the 1692 witchcraft hysteria began. Tour the Rebecca Nurse Homestead — the preserved 17th-century home of an accused witch — and a replica of the village meetinghouse where preliminary hearings of accused witches were held, then visit the Witchcraft Victims’ Memorial, honoring the 25 people who died as a result of the mania.

Hunt Ghosts in a Castle

With its turret, 84 stained-glass windows, and maze of antique-filled rooms, Wilson Castle, in Proctor, Vermont, looks like a storybook haunted mansion. During one of its fall candlelight tours, explore the 19th-century castle’s history, learn about its resident spirits, and keep your eyes peeled as guides track any paranormal activity that appears.

Walk Over Burial Grounds

On Providence’s Benefit Street — known as Rhode Island’s most haunted — a ghost tour sets stories of restless spirits against the backdrop of elegant historic houses. Guides reveal how family burial grounds once dotted the hillside and were allegedly moved as the neighborhood grew, along with local lore involving funeral parlors, cemeteries, and a phantom carriage on College Hill.

Descend Into a Pumpkin-Lit Prison

In East Granby, Old New-Gate began as a Colonial copper mine before Connecticut transformed its dark, underground tunnels into a prison in 1773. It’s now a museum, and visitors can descend into those same eerie passageways during Light Into the Dungeon, when 400 professionally carved jack-o’-lanterns illuminate the spooky 100-yard tour.

Investigate a Fort, by Moonlight

At Fort Knox, a 19th-century defense fort on Maine’s Penobscot River, join paranormal investigators on a Ghosts of Fort Knox tour, using night-vision equipment to search granite chambers for unexplained activity until around midnight. Prefer your scares before sundown? A daytime “scavenger haunt” sends visitors searching for spooks.

Still Set on Salem?

Visit on a weekday, reserve attractions well ahead, and get there early. And beat the traffic — commuter trains connect Boston’s North Station with downtown Salem, while the Boston ferry runs through October 31st. Or for the same witchy vibes with fewer crowds, go in early November instead. — R.F.S.

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Nantucket

Have a whale of a time.

Author Herman Melville is thought to have been the first tourist on Nantucket. But he didn’t visit till 1852, a year after publishing his now 175-year-old Moby-Dick, which draws on the island’s former whaling industry (glad that one’s behind us) to tell the tale of one man’s obsession with the infamous white whale. At the time, the editor of Nantucket’s Mirror newspaper lamented that folks were leaving to summer elsewhere.

Today, summer on Nantucket is vastly different, with 80,000 people swarming a place that’s home to 14,500. But come autumn, the island settles into a slower pace, now basking in fall’s glow. To get there, fly into Boston and hop on a puddle jumper to ACK. (That leg is just under an hour.) The Wauwinet (rooms from $375; open through November 1st), an oceanfront Relais & Châteaux hotel, is an ideal place to hang your Eagles beanie. There’s a veranda with firepits so you can savor the cool sea breeze; at Topper’s, the menu entices with the Atlantic halibut on a velvety velouté; and bikes are available for hitting the trails. Ride to ’Sconset, the so-sweet fishing village, or head to Cisco Brewers’ campus, where you can sip beer, spirits, and wine all made on island. (Don your plaid for the Flannel Jam music fest on October 12th.) Or pedal to town, where cobblestone streets lead to modern shopping. For embroidery à la Red Gravy Goods, hit The Makery to get ball caps customized with island icons (I picked hydrangeas). Visit Steplane’s new boutique for Nantucket’s first tartan, and get your island threads for less at the University of Nantucket store. For restaurants, Bloom Bar is a vibey new spot, but the scene at staple Brant Point Grill can’t be beat — picture yachts rock​ing gently on the water as you linger over lunch. Then there’s the ever-present past, preserved in the steps of Melville.

Hit List: Fall is peak cranberry harvest season; Milestone Bog — the oldest and largest continually operated farm on the island — has various community events.

Walking Tour

Notes from Melville’s first (and only) Nantucket trip

Steamboat Wharf
Like modern visitors who come by ferry, Melville arrived by steamer in 1852. (Want to cruise? Nantucket by Water’s charters include a whaling history tour, though they leave from Straight Wharf.)

Jared Coffin House
Formerly Ocean House, where Melville stayed. The three-story Federal-style building later became a boutique inn with a subterranean taproom — perfect for a nightcap.

Thomas Macy House
Melville dined here with its namesake — the son of Obed Macy, who wrote The History of Nantucket, a resource for Moby-Dick.

’Sconset and Sankaty Head Lighthouse
Melville took an island tour to the village and nearby lighthouse, which he described in a letter to fellow author Nathaniel Hawthorne. The lighthouse is undergoing renovations, but you can still peep its red and white facade from Baxter Road. (Grab sandwiches from Claudette’s — open till October 11th — in ’Sconset.)

Pacific Bank
Where astronomer Maria Mitchell, her father, and their family had an apartment, and where Melville visited with the duo.

Nantucket Whaling Museum
No, this wasn’t one of his stops. But here you can learn about the real-life 1820 tragedy of the whaleship Essex, which inspired Moby-Dick, as well as historic art like scrimshaw (a pastime for sailors, who engraved ivory with intricate images) and lightship basket weaving, still popular today. — Kristen Schott

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New Hampshire

Get pampered — or rough it stylishly — at the state’s newest resorts.

Lake Life

Make a splash at this waterfront spa.

With its more than 270 bodies of water, the Lakes Region may sound like the place to be in the summer, but it’s dreamy in the fall — particularly if you spring for some R&R at The Lake Estate on Winnisquam (rooms from $299), in the town of Tilton. (To get there, do as I did and hit the road — it’s a six-hour drive from Center City, and you can visit the Mark Twain House and Museum in Hartford, Connecticut, and the deCordova Sculpture Park and Museum in Lincoln, Massachusetts, on the way.) Opened last August, the posh property has 114 rooms (the majority of which have lake views) as well as a restaurant with fancy country club vibes — think Alpen Rose but with a pastel blue and green color scheme.

There are tons of outdoor activities — apple picking in the orchard, canoeing on the lake — but the main draw is the spa, complete with indoor and outdoor amenities like two saunas, a year-round heated mineral pool, and a garden. Opt for a treatment inspired by the environment; the 24K Crest Signature Ritual is a two-hour experience with a massage, marma point activation, and a tea ceremony to finish. Serenity now.

Hit List: Drive the Kancamagus Highway and stop at the pavilion at Hancock Overlook, from which you can see the turning colors of the White Mountains. — Shaunice Ajiwe

In Tents

Camp out, but better.

You’re going to face an immediate dilemma: Go frolicking in the meadows, drink up the vistas of Mount Washington, or take a nap in your West Elm–furnished tent? Don’t stress. All paths lead to stargazing and s’mores by the campfire. These are the tough choices at Under Canvas White Mountains (tents from $329), a glamping resort set on 86 acres of outlet-free campgrounds (portable chargers are available) that opened earlier this year. It’ll be a welcome respite after the eight-hour drive from Center City. Concierges can recommend active and laid-back adventures, whether that’s hiking (Franconia Ridge is steep yet magical) or fly-fishing the Connecticut River. Don’t miss the waterfall-laden trails of Flume Gorge and the brew​eries of Littleton, both nearby. A cafe at camp offers sit-down meals, grab-and-go options, and cocktails (because a drink is called for after roughing it). The only catch? The season ends October 11th, so plan your trip for next year. — Malcolm Burnley

Published as “Fall Classic” in the October 2026 issue of Philadelphia magazine.