New England is one of the most romantic places in America. While the West Coast certainly offers more breathtaking vistas of craggy mountain peaks, painted canyons, and sprawling desert, there’s nothing quite so charming as a New England village. I don’t know how else to explain it–driving around the small towns of New England feel like you’re inside the coziest 90s movie you’ve ever seen. There’s no better time to drive around the quaintest corner of the United States than the fall.
A word of caution: driving around these states during peak foliage, when the forests are at their most vibrant, may give you Robert-Frost-level beauty, but it’s gonna be you and every other shlemiel on the road. Since I’m a teacher and my Fall Break is always the first week in October, I’ve only seen New England foliage at the early stages of vibrance. But it was still beautiful, and there was hardly any traffic!
Here are some very cute towns and cities I’ve visited in New England that live up to the hype. All of the towns on this list are worth a stopover. You could easily see all of the towns on this list in a week.
CONNECTICUT
Mystic: Definitely one of my favorite towns in the USA. Mystic is aptly-named, because there’s a sense of magic that surrounds this small coastal town. Everything in Mystic is picturesque: a lifting bridge that lets in tugboats, an idyllic main street, and a maritime museum. Even if nautical stuff is not your thing, I would recommend going to Mystic Seaport Museum. They have several old ships in their harbor, a lighthouse, and they offer sailing cruises that will take you around Mason’s Island.
Stop and have a lobster at S & P Oyster Restaurant. Make sure to get a seat on the terrace to watch the ships pass under the bridge! And if seafood isn’t your thing, cross the bridge to Mystic’s claim to fame, Mystic Pizza, home to the eponymous movie starring Julia Roberts. The movie memorabilia alone is worth a stop inside this classic pizza joint that truly feels straight out of 1988. And, because I’m an English major, I would be remiss if I didn’t plug The Ancient Mariner, a burger/steak/seafood restaurant with a nautical theme and a name that borrows from Samuel Taylor Coleridge’s famous poem about a sailor who shoots an albatross and dooms his crew to a nightmarish voyage. Don’t let missing Mystic be the albatross around your neck!
Niantic: Niantic is a book-lover’s dream! Definitely hit up McCook’s Point Park and Beach to watch the sunset on the water, and there’s a classic movie theater that faces the bay. But Niantic’s most magical attraction is Niantic Book Barn. I don’t know how else to explain it: imagine if Lorelai Gilmore and Bilbo Baggins created a tiny theme park that was also a used book store, it would be Book Barn. There’s the actual barn (not pictured), and then there’s all of these little hidey hole areas embedded in gardens all around the sprawling property. Truly the most magical book store I have ever been to in my life. Shakespeare & Company in Paris has NOTHING on Book Barn.
Willimantic: June, 1754. The citizens of the peaceful town of Windham awake in the night to a cacophonous shrieking. It sounds like hordes of agonized demons, rising up from Hell and crying for souls to devour and rip in twain. The shrieking echoes all around them, ricocheting off every coastal cottage. While some pray for their souls, many colonists fear for their lives: the French and Indian War had just broken out a few weeks before, and already several towns were rumored to have been sacked by the French and Algonquian tribes. Could the shrieking be the tribal cry of indigenous Algonquians, coming to sack the town? In a mass panic, a ragtag militia is assembled, ready to defend Windham or die trying. The men, clutching their muskets and pitchforks with trembling hands, head down to the river, where the screaming is loudest. It is there that they discover the source of the terrible din: frogs. Just some ol’ frogs, hopping around, looking for water. It had been a particularly dry spring and already a hot summer, so the rivers were low. All the frogs in the Windham-Willimantic region had gathered in one area where they could find water, and thousands of crispy-fried frog corpses littered the riverbank the next day. To memorialize those brave amphibians who gave their lives during that fateful night known as Frog Fright, the Frog Bridge was built over the Willimantic River.
VERMONT
Vermont is my favorite state in the whole country, so I don’t think you could go wrong with any town here, especially in the fall. Even as I type this, my heart aches for Vermont.
Wilmington: I stumbled upon Wilmington while driving towards Green Mountain National Forest, and it is truly something out of a Robert Frost poem. A picturesque main street, covered bridges, and rolling hills meeting together over a sparkling brook. Dot’s Restaurant sits at the heart of the town. *swoons*
Brattleboro: Half an hour away is Brattleboro, which offers all the same charming Vermont fancies (covered bridges over vibrant red maple trees and golden oaks!) as Wilmington, but Brattleboro is just a little bit bigger. The main street has a little more shopping, and there are more restaurants. Voted the Best Small Town in America by StrongTowns, Brattleboro’s pride is being farm-to-table. So if you go to Brattleboro, PLEASE don’t skip Robb Family Farm! The Robb Family used to run a dairy with award-winning cows. Picture it: rolling hills, black-and-white cows grazing in the pasture… this is some ee-i-ee-i-oh level quaintness. But their real claim to fame is their maple syrup, so now they just focus their energies on running their sugar house. Call ahead and stop by for a tour of how maple syrup and candy is made; the Robb Family is really nice! And don’t leave without taking a bottle (or jug) of their Robust Grade A maple syrup with you. Once you’ve had the darkest, richest grade of maple syrup, you’ll never go back to Mrs. Butterworth’s.
MAINE
Out of all the states in New England, Maine is the one I wish I could spend more time in! Maine has the idyllic imagery of coastal New England, but it also has the wild, untamed forests of Vermont. Hopefully someday I can add Portland/Rockland and Bar Harbor/Acadia to this list. And, because I am of course a Stephen King fan, I would love to visit Bangor to see his Halloween house.
Ogunquit: Definitely one of the most Instagrammable cities on this list. Precious wooden houses in Colonial and Victorian style line the main street. There’s an old movie theater that has been converted into an elegant bar. Ogunquit’s maine attraction (ehehe) is Ogunquit Beach. Which… you know… those gorgeous Atlantic Ocean beaches, amirite? Mmm boy, can’t believe I came all the way from my state, which borders the Gulf of Mexico, to sit on the cold, hard sand and watch people in sweatshirts attempt to climb over barnacle-covered rocks to dip their toes in ice-cold water with the lobsters. Weee!
Or, if you want to save yourself the misery, maybe just enjoy the lovely Atlantic Ocean from a sailboat in one of Ogunquit’s many harbor tours. DEFINITELY get a lobster roll from The Lobster Shack—this restaurant made me change my mind about lobster rolls and clam chowder. HIGHLY recommend. Maine is known for its blueberries, so save some room for Maine blueberry pie ice cream at Charlie’s on the Beach, which is nearby. And for dinner, head over to The Lobster Pound, where you can pick your own lobster, look him in the eye, and tell him he’s going to meet his maker. Then dip him in butter and devour your worthy adversary.
NEW HAMPSHIRE AND RHODE ISLAND
Portsmouth: I’ve only driven through the bottom corner of New Hampshire, but from what I can tell, central and northern New Hampshire are very similar to Vermont: very rural, mostly small towns. Vermont has Green Mountain, and New Hampshire has White Mountain. If you have time to explore the state, don’t miss out on driving Kancamagus Highway. But if you just want to see New Hampshire on your way to Maine, then I would recommend Portsmouth.
Portsmouth is one of New Hampshire’s biggest cities, which is hilarious because the population is around 20,000. It’s very historically preserved, with classic New England wooden houses like what you would see in any cozy fall movie from the 90s. My favorite part of Portsmouth was New Castle Island, which features beautiful Queen Anne Victorian houses facing the harbor.
Providence: Flights to Providence can be pretty cheap, so I’m including Providence here in case you decide to fly in and rent a car to explore New England. Providence is a very blue-collar city with a historic, early-1900s downtown, kind of like Portsmouth. Even though I would dedicate more time to Maine and Vermont than Rhode Island, I found the people to be rough-looking but really friendly. Like a cinnamon roll. We got to our hotel in Providence at 2 in the morning, and as we were unloading out suitcases from this beautiful Mustang, a grizzled-looking guy in a hood made a bee-line toward us. We were like, “oh god… this guy is gonna try to grift us, because we’re in this gorgeous car, and it’s 2AM.” But as he approached us, he said “how you guys doin’? You enjahin’ these cool New England nights?” and went right past us to go smoke at a picnic table. EVERYBODY in Rhode Island was like that, Maine too. Very friendly and approachable, if not a little weather-beaten.
MASSACHUSETTS
I feel like I should include Boston on this list, but like… do you need me to recommend Boston? It’s… fine. I know, I know. How can I, a History Buff and That One Girl in School Who Wrote Fanfiction About the Founding Fathers, not love Boston? I mean, I like it, the Liberty Trail is really cool, but… it’s just not a very pretty city to me. It’s all squat, red brick buildings. I don’t know. Go visit it, I guess. Union Oyster House is cool.
Salem: PLEASE don’t go to Salem for Halloween. Going to Salem for Halloween is like going to New York for New Year’s Eve… you’re never going to be able to find parking, and you’ll be too busy fighting crowds to enjoy the moment. While Salem isn’t the most bewitching city I’ve ever been to (that title would belong to Edinburgh, Scotland), it is chock-a-block full of Halloween stores and crystal emporiums.
Maybe I built my hopes up too much. A True Child of the Nineties, I was raised on Sabrina the Teenage Witch and Hocus Pocus. I am obsessed with the Salem Witch Trials (and any historical event involving mass paranoia). My cat’s name is Salem. So when I went to Salem, I was expecting the same beautiful wooden houses and enchanting main streets that are typical of Connecticut, New Hampshire, Vermont, and Maine. Except, like… spooky to the max.
What I got was essentially a suburb of one of America’s ugliest cities, Boston, featuring more of that stalwart red brick. The *witchiest* part of Salem is Essex Street, a less-cute version of Hogsmeade at Universal Studios. Just as fake. What I was really looking forward to was soaking in as much Salem Witch Trials history as possible, only to be disappointed that there’s only one building left from that time period, the Jonathan Corwin House. It’s called The Witch House because it looks spooky with the right Instagram filter, but its only link to the Salem Witch Trials is that it was the home of the one the judges who presided over the trials, and he was just the guy who wrote the warrants for arrest.
I mean, I get it. The Salem Witch Trials were 330 years ago, and they were an embarrassing stain on Massachusetts history. It’s like the Frog Fright thing all over again, except eight people were murdered. So you can go see a memorial to the eight victims of the Salem Witch Trials, but finding their graves will be tough. Because they were executed as… you know, witches. It’s not like these Puritan families would have given Tituba and John Proctor a big ol’ memorial; they probably were like “quick let’s bury them in the backyard before somebody accuses us as well”. The Salem Witch Museum is worth going to, but it’s a Mannequin Museum. USA Today rated it as the #2 biggest tourist trap in the world, but–and I cannot emphasize this enough–the whole city is a tourist trap.
I know I’m disappointing you. I’m not saying don’t go. Go, by all means! Just don’t carve out a week for Salem when you could go to all the other gorgeous, authentic places on this list. If you go, of course drop by the Hocus Pocus house (but be warned: it’s private property), and have a lobster roll at The Lobster Shanty, which is right across the street from the site of the “I Put a Spell On You” Halloween party from Hocus Pocus.
I know I’m being hard on Massachusetts, it’s just… I haven’t explored enough of it to really get a good impression of it. I’d like to explore some picturesque Massachusetts towns on this list. Maybe you could go for me and tell me which one you would recommend.
There are two possible routes that can be accomplished easily in a day:
- For mountains, trees, and covered bridges: Connecticut, Massachusetts, Vermont. Starting in Norwich/New London, take I-95 to Mystic for lunch, then head towards Hartford to go up I-91 through Massachusetts into Vermont. At Brattleboro, visit Robb Family Farm for a maple syrup tour, then take a left and go to Wilmington, then drive through the Green Mountain National Forest. In the late afternoon, head all the way back to Niantic for dinner, book shopping, and a show.
- For coastal quaintness: Rhode Island, Massachusetts, New Hampshire, Maine: Starting in Providence, head towards Boston and take Highway 1 all the way up through Portsmouth, then head to Ogunquit.
Ramblin' Reba 
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