Explore New England This Fall with These Hidden Gems

Photo via Cavan Images/Getty Images

Please check state and local COVID-19 guidelines before embarking on your next adventure.

In the shadow of Mount Monadnock, Milford’s fall foliage shines even brighter. / Photo via Dennis Tangney Jr./Getty Images


Milford, New Hampshire

Given the state of the world, you could be forgiven for wanting to hop in a time machine and travel back to a simpler era. While that technology, to our knowledge, still doesn’t exist, a day in postcard-perfect Milford sure comes close. The quintessentially New England town center still looks much like it did when Milford was incorporated in 1794, with a central oval, a picturesque gazebo on one end, and the bubbling Souhegan River behind it. You can stroll any number of the nearby parks, paths, and side streets that spiderweb out from this central point, but one of the best ways to take in Milford’s charms is to simply grab a latte from Union Coffee Co., then find a bench and watch as the rhythms of daily small-town life unfold in front of you.

When you’re ready to start your day, join the locals for a hearty breakfast or brunch at the Riverhouse Café, where the photogenic “Compost Heap” (eggs, hash browns, roasted local vegetables, and garnishes like pea shoots) is sure to satisfy. Don’t worry about overindulging—there are ample opportunities here to walk it off. Nearby Tucker Brook Town Forest boasts 285 acres of conservation woods just minutes from downtown. History buffs, meanwhile, should pop by the Monson Center, a former Colonial settlement that’s now considered one of the most archaeologically significant sites in New England for its numerous 18th-century walls and foundations. When you’ve worked up an appetite again, head back downtown to Greenleaf for an epic charcuterie board made from local meats and cheeses.

Stay until dark and you can catch a socially distanced flick at the delightfully retro Milford Drive-In Theater, one of the last of its kind in the Northeast. Bring a lawn chair and some blankets and watch a movie under the stars—not only will you momentarily forget about COVID-19, you might just momentarily forget you’re in the 21st century. —Todd Plummer

Illustration by Joe McKendry

Surprise a Devilish Ghost

Rumor has it that deep in the woods in central Massachusetts, the ruins of a former prison camp still contain spirits that go bump in the night—and if you’re feeling brave, you can actually visit the spooky, little-known spot on a simple day hike. Traipse about 2 miles down Prison Camp Road, a marked, mostly flat dirt path accessed at the 300-acre Rutland State Park, and you’ll eventually encounter remnants of the site—including still-standing, closet-size stone cells and a cavernous root cellar where the farm inmates worked. Massive murals of wild, colorful graffiti now cover the crumbling foundations of the camp, which also included a prisoner cemetery (its 59 graves can be found off nearby Charnock Hill Road) and tuberculosis ward; maybe that’s where Rose, one of Rutland’s supposed lingering specters, left her earthly body behind. —Scott Kearnan

Photo via Tom Duprey/MyHikes.com

Hole up Like a Hermit (for a Day)

New England has never shaken its fascination with hermits, those who’ve abandoned society to live in solitude. Henry David Thoreau is famous for his years at Walden Pond, of course, but there were other lesser-known men who, seeking peace and quiet, decamped to the woods to live in caves. If the chaos of remote work and school already has you seeking a hideaway this fall, here are three you can hike to.

Ode’s Den
Cohasset and Hingham

Drive down I-93 and 3A to Whitney and Thayer Woods to experience “Ode’s Den,” a group of glacial erratics you can climb up and down into. The rocky hideaway along the park’s Milliken Memorial Path is named for hermit Theodore “Ode” Pritchard, who apparently lost his home in 1830 and decided to make a new shelter beneath the rocks.

Hermit Cave Loop

Follow this 4-mile trail deep into the Erving State Forest to find the cave of a Scottish hermit (pictured) named John Smith, who lived under the overhang of a cliff in the late 1800s. Look closely and you can still see remnants of his garden (Smith particularly enjoyed planting potatoes and lettuce) and old stonework.

Hermit Cave
East Thompson, Connecticut

Some speculate that settlers created this rounded stone chamber, now off the Air Line State Park Trail, as a root cellar; others guess Native Americans constructed it. In any case, even if it technically doesn’t deserve its name, Hermit Cave is still a contemplative place to marvel at both natural and manmade wonders. —Madeline Bilis 

Welcome to nature’s waterpark: Warren Falls in Vermont / Photo by Natulka Photography/Alamy


Warren, Vermont

We’re just going to say it: Nothing ruins a leaf-peeping road trip faster than sitting in traffic behind a line of New York and New Jersey license plates. And with social distancing an essential component of just about any getaway these days, this fall it really pays to go where the crowds aren’t. A town that remains a Norman Rockwell–esque vision, Warren, Vermont, is that place, with a charming “downtown” consisting of little more than a hotel, a covered bridge, and a post office—and no shortage of natural wonders to explore outside of it.

Start right in the middle of it all at the Warren Store, one of New England’s most quintessential trading posts, which stocks everything from local craft beers and raspberry bars to soaps made from local botanicals. When you’ve eavesdropped on enough juicy local gossip, grab a couple of spicy Cajun meatloaf sandwiches and hit the road.

There are numerous hiking trails and secluded spots within close reach of downtown, the most beloved being Warren Falls, a granite swimming hole where kids jump from the cliffs during the warmer months. This time of year, however, it’s an easy-to-reach (yet delightfully secluded) spot to take in the best of the season. For longer walks, keep driving south on Route 100 to reach the Blueberry Lake trail network inside the Green Mountain National Forest—naturally an ideal spot to witness fall’s most brilliant colors.

As with most small towns, the end of the day will bring you back to where you started. At the Relais & Châteaux Pitcher Inn on Main Street, foodies will appreciate the main dining room’s 500-bottle wine cellar and farm-to-table menu—but if you ask us, the fireside tables down a nondescript flight of stairs in Tracks tavern are some of the coziest nooks in all of Vermont. —T.P.

Photo courtesy of Winvian Farm

Stay at These Offbeat Hideaways

Penobscot Bay, Maine

A stay at Goose Rocks Lighthouse, nestled between North Haven and Vinalhaven islands in Midcoast Maine, starts with a boat ride and a climb up a 20-foot ladder to reach the tower, where newly minted keepers will settle in for a night surrounded by antiques and Maine paraphernalia. Come morning, the hammock outside is the perfect spot to relax surrounded by water.

207-200-6820, beaconpreservation.org.

Storybook Cottage

Tucked away on the Santarella estate, a popular wedding venue, the cylindrical Silo Studio Cottage is quite literally the stuff of fairy tales, with a 35-foot ceiling and enormous mill windows looking out on the mystical, magical forests of the Berkshires. Take a stroll on the grounds, which feature a real-life “gingerbread house” and gardens, to complete the fantasy.

413-243-0840, tripadvisor.com.


Longing for a weekend away without actually getting away? Hidden in plain sight right in Charlestown Navy Yard, the Green Turtle Floating Bed + Breakfast offers the best of land and sea close to home. Kick back in one of the charming houseboat’s two queen suites, each offering a private bath, homemade breakfast, and jaw-droppingly pretty downtown views from the dock chairs.

617-337-0202, greenturtlebb.com.

Morris, Connecticut

Remember the ramshackle kids’ clubhouse in your neighbors’ backyard? This definitely isn’t it. Soaring 35 feet above the forest floor, the treehouse cottage at Winvian Farm (pictured) includes a fireplace, steam shower and Jacuzzi, and all the other hallmarks of a truly luxe hideaway. When you’re not enjoying the bird’s-eye views of fall foliage from the suite’s second-floor lounge, explore the resort’s 113 acres by foot or bike.

860-567-9600, winvian.com. —T.P.

Photo via Nicholas Erwin/Flickr

Search for These Secret Castles (and Castle Ruins)…

New England is chock-full of Capes and saltbox Colonials, but castles? Only a rare few. In various states of repair, these almost-royal fortresses are worth the drive.

Madame Sherri’s Castle
Chesterfield, New Hampshire

A costume designer for Broadway shows like the Ziegfeld Follies, the glamorously peculiar Madame Antoinette Sherri once lived in this castle in the woods, where she hosted lavish parties. The structure burned down in 1962, leaving only the grand exterior staircase sitting beneath a dense canopy of trees. On an autumn visit, you can envision what the residence must have looked like in its glory days.

Photo via Peter Rintels/Flickr

Gillette Castle
East Haddam, Connecticut

Talk about drama: Commissioned by actor, director, and playwright William Hooker Gillette in 1914, this mottled fieldstone fortress took 20 men five years to complete. Now its grounds are part of a state park, meaning they’re yours to explore. Saunter down the trails surrounding the still-intact castle, which wind through stone-arch tunnels and over wooden trestles.

Photo via Troy B. Thompson/Flickr

Bancroft Tower

Wormtown may be known for its old mill buildings, but this boulder-and-cobblestone tower hidden in plain sight proves there’s more to the city than meets the eye. Measuring 56 feet tall, the imposing structure on a hill in Worcester’s Salisbury Park was built in 1900 to honor former secretary of the U.S. Navy George Bancroft. After a stroll around the park, make note of the two half-compasses on either side of the tower: They symbolically point to the other six of Worcester’s seven hills. —M.B.

Illustrations by Joe McKendry

A view of Monhegan Island’s picturesque harbor. / Photo by Benjamin Williamson


Monhegan Island, Maine

Hardly any cars, definitely no paved roads, and rugged ocean views as far as the eye can see: A day trip to this island (population: 69), situated 11 miles off the coast of Midcoast Maine, offers an off-the-grid experience not easily found in New England. And this time of year, after the summer rush, you’ll find even more solitude.

After roughly an hourlong ferry ride from Port Clyde or Boothbay Harbor, your journey begins on the dock at The Barnacle, a go-to spot for fresh-roasted coffee and homemade snacks made on-island. There are trail maps you can pick up on the boat, but, frankly, it’s nearly impossible to take a wrong turn on this one-square-mile island—so why not ditch the directions and find your inner adventurer? Make your way over to the soaring granite cliffs found on the secluded eastern shore, then keep tramping your way down south to Lobster Cove, where you’ll discover the rusty wreck of a 1940s tugboat. Here on the island’s southern end you’ll also find Monhegan Brewing Company, the locals’ preferred (read: only) craft-beer hot spot. Order a Rope Shed Red amber ale and rest your legs at one of the picnic benches, and you’re more than likely to see some townies bust out their fiddles and start jamming.

Before heading back to the ferry, stop at Monhegan Fish House for lobster BLTs and a steaming cup of clam chowder to go. Most important, make sure you pick a posy of local wildflowers to toss off the stern as the ferry sets sail—it’s a Monhegan tradition that lets the islanders know you’ll return some day. —T.P.

Constructed in 1874, Putnam’s historical town hall is worth strolling by en route to the antiques shops. / Photo via Stan Tess/Alamy Stock Photo


Putnam, Connecticut

Not too long ago, the region known as Connecticut’s Quiet Corner was simply a place you whizzed by on 395 en route to the casinos. But the area has recently emerged as a stop in its own right—particularly the tiny town of Putnam, where first-rate antiquing and a newly amped-up dining scene make for a worthy day trip just over an hour from Boston.

Before you begin your shopping excursion, fuel up at Victoria Station Café, a Gilmore Girls–esque coffee shop that serves lattes in a variety of flavors (the iced “sappy” chai, sweetened with maple syrup, is perfect for sipping on the front terrace). You’ll need the energy for exploring the legendary Antiques Marketplace, one of the oldest antiques mega-malls in the state. Built as a department store in 1880, the building’s 20,000 square feet are spread across four floors, hawking everything from 18th-century fine art and glassware to vintage Pyrex and costume jewelry. Afterward, stop for a lunch of bangers and mash on the patio at the Hare & the Hound, a nearby Irish pub slated to open this fall.

Photo via Stan Tess/Alamy Stock Photo

Your treasure hunt isn’t over yet: The next stop is Jeremiah’s Antiques & Collectibles, where the glass cases overflow with toys, comic books, sports memorabilia, and military trinkets. Don’t miss the quirky, free “Celebrity Musuem,” a corner at the back of the shop decked out with old movie props and costumes. Once you’ve found a piece of history to bring home, you can tuck into decidedly modern fare—think: a special featuring Point Judith fluke with nasturtium butter—at the restaurant 85 Main—before toasting to a day well spent with a pint of vanilla coconut porter from the newly opened Bear Hands Brewing Company. —M.B.

Photo courtesy of the Trustees

Search for Dino Tracks

Did you know Massachusetts has a state fossil? Surprisingly, it’s not Plymouth Rock—it’s dinosaur tracks. Some of the first Jurassic Period footsteps ever to be recorded by scientists are trapped in red sandstone in Holyoke. Paleontologists discovered the treads back in 1802, and it’s now understood that about 200 million years ago, the Connecticut River Valley was home to subtropical wetlands and lakes. At the Trustees’ Dinosaur Footprints Reservation, you can glimpse hundreds of prehistoric steps of some of the earliest-known dinosaurs, including smaller herbivores and much larger 20-foot-long meat eaters. Follow a dirt path from the entrance to find them. —M.B.

Photo by Mona Miri

Explore All Saints Way

You’ve probably eaten at the North End’s red-sauce joints more times than you can count, but have you ever ducked into the neighborhood’s semi-hidden shrine? Tucked away off Battery Street, this trash-bin storage area turned museum showcases an impressive collection of framed portraits, prayer cards, collages, and saint statuettes created and maintained by lifelong resident Peter Baldassari, who got the idea to build the shrine almost 30 years ago. Locals say he opens the gate to All Saints Way almost every morning, but if you happen to visit and find it closed, don’t despair. Look up to spot saintly photos on the brick walls of the alley almost three stories high. And make note of the famed sign above the doorway: “Mock all and sundry things, but leave the saints alone.” —M.B.

Photo by Mona Miri

Hunt Down These Roadside Attractions

Desert of Maine
Freeport, Maine

Given that traditional travel isn’t in the cards these days, heading to New England’s hidden “desert” might be the closest you’ll get to one anytime soon. Currently open for self-guided tours, this huge deposit of glacial silt resembling the sandy Sahara is the main draw at this Freeport landmark, which was recently revamped by its new owners.


Thetford, Vermont

What’s a road trip without stopping at a huge, kitschy roadside icon? Made of scrap wood by a retired schoolteacher, this 122-foot-long dino lives in a field near the Post Mills Airport in Thetford.

JFK’s Rejected Grave Marker
Newport, Rhode Island

When stone carver and Newport resident John Benson was tapped to design John F. Kennedy’s grave marker at Arlington National Cemetery, he envisioned encircling the grave with quotes from the president’s inaugural address. Benson started by carving the quotes into several slabs of stone, but later scrapped the idea in favor of a different design. Spy one of his rejected slabs at 95 Church Street in Newport, next to the entrance to the Boys & Girls Clubs.


This collection of hobby horses off a back road in Lincoln (pictured) is shrouded in mystery: Since 2010, an unknown entity has rearranged the position of dozens of rocking horses, creating a toy graveyard of sorts. Cruise down Old Sudbury Road to spot them. —M.B.