8 Quirkiest New England Towns To Visit In 2026
Homemade weirdness is a specialty of the small towns of New England. The quirkiest landmarks here were rarely built to draw tourists at all. A grieving artist raised a chapel to dead dogs because he needed to. A frustrated sculptor stacked file cabinets into a tower to needle city hall. That homemade streak is the real appeal of a New England detour. Each of these eight towns is home to one landmark no committee would ever have approved.
Waterbury, Vermont
Behind the Ben & Jerry's factory in Waterbury, Vermont, is a hillside plot of real granite headstones. This is the Flavor Graveyard, a display of discontinued pints with an epitaph on each. Holy Cannoli and Dastardly Mash each have a marker, and visitors read the mock-mournful verses free of charge. The factory tour up the hill is open year-round and ends, predictably, at the scoop shop.
The rest of Waterbury is worth a slow afternoon. Bridgeside Books has a tight, well-chosen shelf a few steps from the Winooski River. The Cabot Creamery store is the place for the cheddar the region is known for. Between the two, there are enough parks and trailheads to fill the gap before dinner.
Woodbury, Connecticut
Statistician Edward Tufte built an open-air sculpture park on 234 acres in Woodbury, Connecticut. Hogpen Hill Farms is home to about 100 of his large steel and stone works, spread across meadows and ridgelines. The pieces are massive and geometric, set out across the open fields with room between them. Tufte opens the grounds to the public on select weekends, so a visit takes a little schedule-checking.
Two more Woodbury stops round out the day. The Glebe House Museum is an 18th-century home paired with a garden designed by the English horticulturist Gertrude Jekyll. Nearby, the Highwire Deer & Animal Farm is a hands-on spot where families feed a mix of farm and exotic animals. Both are close to the long main-street stretch of antique shops.
Provincetown, Massachusetts
The Pilgrim Monument in Provincetown, Massachusetts, is the tallest all-granite structure in the country at 252 feet. Its designer modeled it on the Torre del Mangia in Siena, Italy, an odd sight to find on outer Cape Cod. It commemorates the Mayflower's first American landfall in 1620, weeks before the Pilgrims moved on to Plymouth. The climb to the top is 116 steps and 60 ramps, ending at a harbor view from the highest point in town.
Down at the tip of the Cape, the Race Point Lighthouse is just behind Race Point Beach. The 1876 iron-plated tower is out on the dunes, reachable by a sandy walk or an off-road permit. History-minded visitors can also stop at Pilgrims' First Landing Park to see where the 1620 story started.
Burlington, Vermont
Artist Bren Alvarez welded 11 file cabinets into a 40-foot stack on Flynn Avenue in Burlington, Vermont, in 2002. He gave it 38 drawers, one for each year of delay on a stalled local highway project. Alvarez bills it as the world's tallest filing cabinet, a title also claimed for a 65-foot piece in Napa. Birds nest in the top drawers, which is a first for a public sculpture in Vermont.
The pedestrian Church Street Marketplace is the walkable center of town. Its four blocks include more than 100 shops, plus buskers and patios that crowd up the moment the weather turns. Foam Brewers is down by the Lake Champlain waterfront, a short walk from the marketplace crowds.
East Corinth, Vermont
Tim Burton filmed much of the 1988 movie Beetlejuice in East Corinth, and the setting is still recognizable. The white-steepled center and the Victorian houses are visible onscreen behind the film's covered bridge. Fans walk the same roads the Maitlands drove and pick out the buildings frame by frame. A local walking tour links the filming spots for anyone who wants the full circuit.
The movie link continues up at Northeast Slopes, the ski hill just outside town. The crew built a covered bridge for the film, and after shooting, its structure was reused as the lift shack for the beginner rope tow. Open since 1936, Northeast Slopes is the oldest continuously operating rope tow ski area in the United States. Lift tickets are cheap, the tows are still powered by car engines, and the East Corinth General Store is the spot for lunch.
Chesterfield, New Hampshire
A Ziegfeld Follies costume designer built a stone chateau in the Chesterfield, New Hampshire, woods around 1930. Antoinette Sherri threw lavish parties there until she went broke, and the empty house was lost to vandalism and a fire. After a 1962 fire, only the foundation, the chimneys, and a dramatic stone staircase are left. The upper arch of that staircase fell in 2021, so the ruins are now roped off and viewed from below.
Several miles of quiet trails run through the surrounding Madame Sherri Forest, past stone walls and hemlock stands. The ruins are a short walk from the Gulf Road trailhead. Over the state line, the 1879 Creamery Covered Bridge in Brattleboro, Vermont, is an easy add-on, and the Chesterfield Inn is the area's better dinner option.
St. Johnsbury, Vermont
Woodcut artist Stephen Huneck built the Dog Chapel on a hilltop above St. Johnsbury, Vermont. The white church was built with steepled pews and a winged Labrador for a weathervane. Inside, mourners have papered every wall, top to bottom, with photos and notes to pets they have lost. Admission is free, and dogs run leash-free across the 150 acres of the surrounding Dog Mountain.
Two more stops downtown are worth an hour. The Fairbanks Museum & Planetarium is a Victorian hall of taxidermy and the state's public weather station. Secondhand Prose is a used-book store for the drive home, and The Buttery is the pick for a sit-down lunch.
Bangor, Maine
A 31-foot Paul Bunyan is the landmark of downtown Bangor, Maine, a double-bit axe in one hand and a logger's peavey in the other. Locals put up the fiberglass giant in 1959 to mark the city's 125th birthday and its lumber-capital past. Residents even call Bunyan a native son, the kind of tall-tale civic pride the statue was built for. Local author Stephen King wrote a menacing cameo for the statue in his novel It, so horror fans photograph it too.
Families have more to do a few blocks away. The Maine Discovery Museum is three floors of hands-on exhibits for younger kids. In fair weather, the Orono Bog Boardwalk is a mile-long walkway out over a working peat bog full of birds and carnivorous plants. The Butcher The Baker is the dinner pick for dishes like schnitzel and Korean wings when the walking is done.
Plan the Detour
These eight stops share one trait: each is defined by a landmark no other town could claim. A pet cemetery for ice cream, a staircase to nowhere, and a chapel for dogs are not the kind of attractions a tourism board plans. People built them over decades, one eccentric artist or stubborn ski club at a time. New England is dense enough that a Vermont sculpture park and a Maine lumberjack are only a few hours apart. Fall foliage season, the busiest stretch for visitors, is the natural window for a trip through several of them.
