7 New England Towns With Unforgettable Main Streets
In Bristol, Rhode Island, the double yellow line down the middle of Hope Street is painted red, white, and blue. Not for a weekend. All year. That is the kind of commitment a Main Street has to make to be genuinely unforgettable, and New England has more of them than it has any right to. Nine towns follow, each with one street doing an unreasonable amount of work: a candy counter holding a world record, a whaleship that is the last of its kind on earth, a bookstore with creaky floors and a social conscience. Bring comfortable shoes and an appetite.
Bristol, Rhode Island
Bristol has thrown the same party every year since 1785, which makes it the oldest continuous Independence Day celebration in the country. Reverend Henry Wight, a Revolutionary War veteran, held the first Patriotic Exercises nine years after the Declaration was signed, and the town has not missed a beat since. Things kick off on Flag Day in June and build for nearly three weeks.
The parade itself draws crowds well into six figures, which is remarkable for a town of about 23,000, and the route runs straight down Hope Street past the clapboard houses and shopfronts. Serious spectators stake out spots the night before, though the official rules say no chairs before 5 a.m. Come any other week of the year and Hope Street is a quiet run of shops and restaurants on Narragansett Bay, with that painted stripe as the only clue.
Great Barrington, Massachusetts
About 7,000 people live in this corner of the southern Berkshires, and the downtown cultural district packs in more than the population would suggest. The Mahaiwe Performing Arts Center anchors it, a restored theater whose name comes from a Mohican word meaning roughly "the place downstream," a nod to the Housatonic running past.
A few doors along, Fuel Coffee functions as the town's informal living room, espresso and odd art on the walls. Yellow House Books carries a used selection that would hold its own in a city ten times the size. It is the sort of street where you go in for a coffee and come out two hours later holding a novel you had not heard of.
Woodstock, Vermont
Woodstock is a town of about 3,000 that looks like it was assembled for a film set and then left alone. The Main Street is lined with eighteenth and nineteenth-century buildings, and F.H. Gillingham and Sons has been selling maple syrup, jams, and general-store goods from the same spot since 1886. Woodstock Scoops handles the ice cream, made with Vermont dairy.
The Norman Williams Public Library does duty as the town's cultural center, and the Middle Covered Bridge over the Ottauquechee is the photograph everybody takes. If you want to stay in the middle of it, the Woodstock Inn and Resort is right on the green.
Camden, Maine
Camden sits at the foot of the Camden Hills on Penobscot Bay, roughly three and a half hours up the coast from Boston, and the schooners tied up in the harbor are working windjammers rather than scenery. Main Street runs past the Camden Opera House, an 1894 venue restored to handle music, film, and theater.
Long Grain, slightly off the main drag, turns out Thai food good enough that people drive from Portland for it. The Smiling Cow has been selling fudge and maine-shaped trinkets to visitors since 1940. Walk down to Harbor Park when you are done and look up at Mount Battie, which is the shot on every postcard in the shop you just left.
Brattleboro, Vermont
Brattleboro runs on an independent streak that shows up in its institutions. The Brattleboro Museum and Art Center works out of the old Union Station, and the Latchis Theatre is a 1938 Art Deco survivor still showing films. On the first Friday of every month, Gallery Walk opens studios and storefronts across downtown, free, which is about as literal a welcome as a Main Street can offer.
The Brattleboro Food Co-op is community-owned and takes local sourcing seriously. Everyone's Books stocks literature and social justice titles across creaky floors, and the River Gallery School of Art runs classes open to anyone who wanders in. It is a town where the commerce and the culture are the same thing.
Mystic, Connecticut
Mystic built ships for a living, and the museum it grew into holds something genuinely singular: the Charles W. Morgan, launched in 1841 and the last wooden whaleship left in the world. Mystic Seaport took her back to sea in 2014 for a 38th voyage after a five-year restoration, which is not something most museum pieces can claim.
In town, the Mystic River Bascule Bridge still lifts for sailboats on the hour in summer, and standing in line at Mystic Drawbridge Ice Cream while it goes up is basically the local rite of passage. Bank Square Books brings authors through regularly, Lighthouse Bakery handles the coffee and pastries, and Mystic River Park at the end of the street is where you sit down and watch paddleboarders go by.
Newburyport, Massachusetts
Newburyport sits on the south bank of the Merrimack north of Boston, and it has a decent claim to being where the U.S. Coast Guard began; the first revenue cutter, the Massachusetts, was built here in 1791. The abolitionist William Lloyd Garrison was born in town in 1805. The brick Main Street and Market Square carry the shops and restaurants.
The Tannery Marketplace, a short walk off Main, holds artisan shops and a farmers market in a converted mill complex. Joppa Fine Foods does cheese, charcuterie, and specialty imports for lunch. The Old South Presbyterian Church, built in 1756, is the building people stop to photograph, and the Custom House Maritime Museum, in the 1835 customs house, covers the years when this was one of the busiest ports in the country.
Exeter, New Hampshire
After the royal governor fled Portsmouth in 1775, New Hampshire moved its capital to Exeter and kept it here for fourteen years. Delegates met in this town in December 1775 and ratified the state's first constitution on January 5, 1776, months before the national Declaration. That is a lot of history for a Water Street you can walk in ten minutes.
The American Independence Museum occupies the Ladd-Gilman House, a National Historic Landmark, and holds a Dunlap broadside, one of the first copies of the Declaration ever printed. Phillips Exeter Academy, founded in 1781, keeps the town supplied with students and lectures. Water Street Bookstore is the independent everyone recommends, and the Exeter Bandstand is where the town gathers by default.
Littleton, New Hampshire
Littleton's Main Street has a world record on it. Chutters, behind a purple and pink storefront, runs a candy counter 112 feet long, certified by Guinness as the longest continuous one anywhere, with more than 500 jars along it. Sorting through seventy flavors of jelly bean takes longer than you expect, and nobody rushes you.
The shop traces back to a general store the Chutter family opened in the late 1800s, and in a state that votes first, it has become a required stop for presidential candidates working the primary. Beyond the candy, this is a White Mountains town with a covered bridge and a grist mill on the Ammonoosuc River a short walk from the shops, which is a reasonable way to walk off the fudge.
What Makes A Main Street Stick
None of these nine work because of the architecture, though the architecture helps. They work because somebody kept something going: a candy counter measured to the inch, a parade unbroken since 1785, a whaleship nobody let rot, a gallery walk on the first Friday for decades running. Bristol paints its center line three colors and means it. Littleton has a Guinness certificate on the wall of a candy shop. Those are not marketing decisions, they are habits, and habits are what make a street worth walking twice.
