10 Most Breathtaking Towns In New England
The leaves are turning as you read this. Northern Vermont, the White Mountains, and western Maine are at or near peak right now, in a season foliage watchers are calling one of the most vivid in years, and the colour is working its way south toward Boston and the coast over the next three weeks.
New England packs six states into an area smaller than Washington and still fits mountain summits, working harbors, offshore islands, and some of the oldest main streets in the country into it. These ten towns are the ones worth planning a trip around, running from the Maine woods down to the Connecticut shore.
Greenville, Maine
Hugging Moosehead Lake in the heart of Maine's Highlands, Greenville is the gateway to the state's great outdoors. Most people associate Maine with its coast, but this inland town has its own case to make. Moosehead runs about 40 miles long and up to 10 miles across, making it the largest lake entirely within Maine and the anchor of everything here. You can eat on the waterfront at Kelly's Landing, but the best views require getting wet or getting airborne.
For the aerial version, Jack's Air Service is known for its seaplane tours. Alternatively, climb Mount Kineo, a rugged peninsula sitting inside the lake with a cliff face rising about 700 feet straight out of the water. If you prefer the view from the surface, the Steamboat Katahdin has been working this lake since 1914 and runs cruises, or you can paddle on your own with gear from Northwoods Outfitters. Their guided moose tours are the best odds you will get of seeing one.
Kennebunkport, Maine
Kennebunkport is the town most people are picturing when they picture coastal Maine. Sitting on the state's southern coast, this former shipbuilding settlement has been a vacation town for well over a century. Whether you pass through for an afternoon or book a few nights somewhere like Mabel's House, it holds up.
Dock Square is the center of it, sitting right on the Kennebunk River and clustered with independent shops and cafes including Coastal Jewelers and Dock Square Coffee House. The architecture does as much work as the businesses: these are 19th-century storefronts, and the square has a genuinely frozen-in-time quality because the building stock never got replaced. Intown Trolley runs sightseeing tours from here, and Blowing Cave Park down the coast is worth the short drive for the shoreline.
Littleton, New Hampshire
Bounded by the Connecticut River in New Hampshire's White Mountains, Littleton is one of New England's prettiest small towns and a quieter proposition than Kennebunkport. The downtown runs along the Ammonoosuc River, dense with boutiques and restaurants, and the Main Street has won awards for it.
Walk it and the riverfront views come with you, whether you are having a beer at Schilling Beer Co or crossing the Riverwalk Covered Bridge. There are no retail giants here. Instead you get the Little Village Toy & Book Shop, Just L Modern Antiques, and Chutters, which holds the Guinness record for the world's longest candy counter at 112 feet.
Stowe, Vermont
Set between the summits of Mt. Mansfield and Spruce Peak, Stowe has a four-season playground in its back garden. Main Street is the prelude, with old-timey general stores like Stowe Mercantile, and then the mountains take over, whether that means skiing Stowe Mountain Resort or riding the Gondola SkyRide in summer and autumn.
From spring through autumn, Stowe is also the way into some of Vermont's best covered bridges and waterfalls. The Historic Gold Brook Covered Bridge is on the way to Moss Glen Falls, a series of drops totalling around 125 feet that is usually cited as the tallest waterfall in the state. It sits a quarter-mile from the trailhead, so you do not need to be a hiker to reach it. Bingham Falls is smaller but just as good, on a similarly short walk.
Montpelier, Vermont
Twenty-two miles southeast of Stowe, Vermont's state capital is the smallest in the country by population and the only one without a McDonald's, which residents will tell you about. Backed by hills, the town overlooks the point where the Winooski and the North Branch meet, and the downtown has stayed independent as a result of a few deliberate decisions rather than an accident.
The State House anchors it, a Greek Revival building with a gold dome, next to the Vermont Historical Society Museum. Further along State Street the river views open up before you reach Main Street spots like the Bohemian Bakery and Bear Pond Books. North Branch River Park, a few minutes out, has trails along the water if you want green space rather than shopfronts.
Salem, Massachusetts
Over in coastal Massachusetts, Salem runs on two histories at once: a serious maritime past and the 1692 witch trials, which the town has spent four centuries working out how to handle. The result is an unusual mix of museums, historic sites, and shops you will not find anywhere else, with waterfront green space at Salem Willows Park when you need a break from it.
Essex Street is a pedestrian-only cobblestone stretch running through the middle, and your day on it can be as ghoulish or as ordinary as you like, from the Salem Witch Board Museum to Wicked Good Books. Salem Maritime National Historic Site covers the other side of the story across nine acres of wharves, a custom house where Nathaniel Hawthorne worked, and a replica of the 1797 East Indiaman Friendship. A word on timing: October draws hundreds of thousands of people here and the town sells out early, so book ahead and take the ferry or commuter rail from Boston rather than driving.
Nantucket, Massachusetts
Around 30 miles off the Massachusetts coast, Nantucket owes most of its beauty to a long-standing commitment to conservation. More than half the island is protected from development, which is why the shoreline looks the way it does. Among its roughly 82 miles of coast, public beaches like Steps Beach stay natural, with no boardwalk arcades or high-rise resorts anywhere.
The town itself was the whaling capital of the world in the early 19th century, and the Whaling Museum occupies a former candle factory with a 46-foot sperm whale skeleton hanging in it. The Shipwreck & Lifesaving Museum handles the other half of that history. Because the island sits so far offshore, the night skies are genuinely dark, and the Loines Observatory opens for public viewing nights.
Westerly, Rhode Island
Beaches and a walkable downtown are the hallmarks of Westerly, Rhode Island's southwesternmost town. This former shipbuilding and granite-quarrying center has been a vacation spot for more than a century. In warm weather give a day to Misquamicut State Beach; when the weather turns or you need a break from sand, the downtown is waiting.
Running parallel to the Pawcatuck River, downtown Westerly has a proper main-street feel, with wide-windowed shops and broad sidewalks. High Street holds the best of it, from coffee houses like Perks & Corks to the Living Sharks Museum, which is exactly as niche as it sounds. Wilcox Park next door is the follow-up, with manicured lawns around a fountain, a pond, and the Westerly Library.
Newport, Rhode Island
About 40 miles east of Westerly on Aquidneck Island, Newport built its reputation on Gilded Age money. The summer "cottages" the Vanderbilts and their rivals put up here are now museums, and The Breakers, finished in 1895 with 70 rooms, is the one everybody sees first. The 3.5-mile Cliff Walk runs behind a string of them with the Atlantic directly below, and the southern half turns to rough rock, so wear proper shoes.
Bowen's Wharf is where you go afterwards. Billed as the anchor of the Newport waterfront, it has more than 30 restaurants and shops, and after a lobster roll at Luke's it doubles as the departure point for harbor cruises with operators like Coastal Queen. Newport is also the home of American yacht racing, having hosted the America's Cup for 53 years until 1983.
Mystic, Connecticut
Ending in Connecticut, Mystic is another former shipbuilding hub that became a vacation town. It is not technically a town at all but a village split between Groton and Stonington, straddling the Mystic River where it runs down to the Atlantic. The bascule bridge on Main Street goes up on the hour through the summer, stopping traffic while a boat passes, and nobody minds.
The Mystic Seaport Museum is the reason most people come, and it is more than a museum: a recreated 19th-century coastal village with a working shipyard and more than 500 historic vessels. The centerpiece is the Charles W. Morgan, launched in 1841, the last wooden whaleship in the world and the oldest surviving American merchant vessel. The Collections Research Center holds over two million artifacts. For the water itself, Argia runs sailing cruises and Mystic River Park has the boardwalk.
Picking Your Town
Narrowing New England down gets easy once you decide what you actually want. Stowe and Greenville are the outdoor picks in any season, Nantucket and Westerly are for warm weather, and Littleton and Montpelier are the ones for a slow day of shops and riverfront. Salem and Mystic lead on history, with the caveat that Salem in October is a different and much busier town.
If you are travelling this month, the colour arrives in stages. Greenville, Littleton, Stowe, and Montpelier are at or near peak now, southern coastal Maine follows around mid-October, and Salem, the Rhode Island towns, Mystic, and Nantucket turn late October into early November. Columbus Day weekend is the busiest stretch of the New England year, and Stowe, Salem, and the White Mountains towns sell out first.
One practical note on geography: this list spans roughly 400 miles, from the Maine Highlands to the Connecticut shore. The Rhode Island and Connecticut towns are within an hour of each other, the two Vermont stops are twenty minutes apart, and everything else needs its own trip. Pick a corner rather than a circuit.
