September 13, 2025, 11:11 am | Read time: 11 minutes
TRAVELBOOK author Anna Wengel (now Chiodo) explored another part of the U.S. by car. Her New England road trip started in Boston and went through parts of Massachusetts, Connecticut, Maine, and New Hampshire. She has written down the nearly three-week route and tips for the journey for us.
I love New England. Especially Boston and the Gilmore Girls town of New Milford. Particularly Jackson and the White Mountains, as well as small coastal towns like Kennebunkport. Thanks to a friend’s wedding near Boston (and despite the Trump administration), I was able to rediscover these and other places on a family road trip through New England.
Our New England road trip route: from Boston to Connecticut, back to Massachusetts, then to Maine and New Hampshire, and back to Boston. We spent a month in the Northeast U.S., with nearly a week and a half in Boston alone. Something I highly recommend to anyone who hasn’t been there (or, like me, wants to return). For me, Boston is a city dream—a big city with all the cafes, culture, shopping, hustle, and opportunities I need to feel comfortable. It’s near the water, with pretty houses and almost quiet places, so those needs are met too. I can’t count how many times my husband and I said how well we could imagine living there, if not for the current political situation.
Overview
Connecticut and Massachusetts
A Small Detour to New Milford
Despite my love for Boston, this road trip doesn’t start in Boston, but from there. Specifically, in Connecticut. From Boston, I took a short trip with my daughter to the almost idyllic state, specifically to New Milford. The charming small town is nothing less than the inspiration for the series “Gilmore Girls.” To get there, we drove directly from Boston via the highway—something you should avoid in order to set the tone for the entire New England road trip.
I didn’t want to subject my nearly four-year-old and myself to too much time in the car, but after two and a half hours of driving, I was completely exhausted by the number of cars and the rushed driving of others. On the way back (from New Milford to Groton in Massachusetts), I opted for a four-hour drive instead. Our experience: a relaxed drive over winding roads, past countless pretty New England houses, through forests and small towns. There was some traffic on the few larger roads, but it was far more relaxed than the highway chaos of the outbound trip. Hence, my decision for the rest of the trip and a tip for anyone planning something similar: no highways. Instead, turn off the highway option in the GPS and enjoy. Plus, you won’t pay tolls, which is a nice, albeit not overly noticeable, side effect.
Also interesting: These Places Are Worth Visiting on a Road Trip From New York
Salem
From Boston, we head north. The first stop on the way: Salem, about 40 minutes away. The name probably rings a vague or strong bell, right? Salem is known as the city of the witch trials. Witch museum, witch house, Halloween shops, and giant skeletons practically crowd the place. As well as the opportunity to dress up and be photographed as a witch.
Salem becomes particularly exciting, as you might expect, around Halloween. While we only saw two girls with witch hats and brooms during our visit, the city is said to be teeming with little and big witches and wizards at that time.
Portsmouth
Continuing north along the coast on our New England road trip, we head to Portsmouth. I should mention right away: The drive from Boston to Portland (Maine), where we’ll soon arrive, takes about three and a half hours. So you can easily find one or two accommodations in between and travel back and forth or move from place to place.
Portsmouth itself is one of the larger towns on the coast and one that, in my experience, particularly attracts younger tourists. For example, on Congress Street, you’ll find not only various nice shops and boutiques but also several hipster cafes. One that combines good coffee with shopping is the NOA Cafe.
We continue over the Sarah Mildred Long Bridge, past towering white stone towers, into Maine. Already up here, with a view of the small, pretty houses by the water, the image of Maine with its charming fishing villages is fulfilled. However, we don’t arrive there just yet, as we first drive through Kittery, an outlet paradise or shopping hell, depending on your perspective.
Maine
Ogunquit
The first fishing village high on my list of charming coastal towns in Maine is Ogunquit. Known as a popular LGBTQ+ destination, artist town, and picturesque village, I definitely want to get to know this truly charming village of about 1,600 people. And of course, since we’re in Maine, eat lobster. You can find it at Barnacle Billy’s with a view of the water and classic American white houses. Welcome to Maine.
Kennebunkport
From Ogunquit, we continue to Kennebunkport. And once again, I’m rewarded with New England fishing village charm. Enchanting, wood-clad New England houses in green, blue, pink, and more, with the ever-present wooden chairs or swings on their porches. By the way, this is a picture that runs throughout the entire trip. If I were to describe New England in one image, it would be colorful autumn leaves in the fall, but year-round, it’s those charming houses that are almost everywhere. At least, as long as you’re in the small towns. What else can Kennebunkport offer? Lobster and other seafood, of course. As well as various boutiques and, of course, the beach. We’re now constantly on the coast, so there are plenty of beaches. Here’s a tip for those seeking peace, and one for those who like to have others sitting right on their towel.
Nearby Beaches
Taking a road trip through New England in July means heat, and the desire for seawater is strong. At least for us. So we set off to visit the beaches. At the beaches around Kennebunkport, you should expect to pay around $25 for parking. We hardly saw any hourly parking fees here. Additionally, depending on the location, there may be a lack of parking spaces. July is also vacation time in the Northeast U.S. I suspect it’s much emptier here outside the peak season.
Now to the two beach tips: If you’re in the mood for a party-like atmosphere, you should move your beach visit to Old Orchard Beach. Attracted by the old, elegant-sounding name alone, I almost drove away screaming. In short: body next to body on the beach. On the pier, which looks so romantic in pictures, fast food and arcades are side by side. Plus, blaring techno noise from cheap-sounding speakers. Get out of here.
We finally found peace south of Kennebunkport. If you don’t care about any facilities at the beach and just want to swim, read, or walk, Parson’s Beach is a suitable, secluded, publicly accessible private beach. There are a few free parking spaces right by the beach. If you don’t mind a ten-minute walk, you’ll find a few more parking options a bit further away. There aren’t many, so the beach is correspondingly empty.
Portland
Through Scarborough, we continue to Portland, Maine. If you’re in the mood for a bit of city life, you can plan a few days here to discover the lighthouse and the popular downtown with its industrial charm, various boutiques, and hipster cafes. The supposedly best coffee in Portland: According to Food and Wine, it’s Coffee by Design. Following this tip, I would agree that the coffee there is really good. Given the abundance of hipster cafes, I wouldn’t swear it’s the best and suggest trying several of the really good coffee shops. At least as good, if not better, is, for me, the Flat White at Bard Coffee.
Yarmouth and Freeport
We make a small detour a bit further north because we obviously haven’t had enough of the region’s small towns, on one of our Portland days to Yarmouth and Freeport. There’s not much going on here, but the nice small-town charm is present.
Acadia National Park
At this point, a tip I didn’t follow myself: Take more time for Maine. Because everything Maine has to offer in terms of true natural beauty seems to be in the north, not far from the Canadian border. Acadia National Park, further north, is, according to my research, a must, as are numerous small fishing villages that probably more closely match the image of Maine I have in my head. One of these: Bar Harbor, one of the most beautiful small towns in the USA. I’ll report back when I go next time. Because, for sure, this wasn’t my last road trip through New England.
Sebago Lake
From Portland, we head in the other direction, out of Maine and into the White Mountains. With a stopover: Sebago Lake. Another classic vacation spot by the lake. We’re here mainly because of a charming-looking lake house, which I unfortunately can’t recommend. The surroundings themselves, however, I can. If you like the classic vacation home by the lake life, you’ll find a nice, relaxed place here. Many vacation homes offer direct lake access via docks. Mostly, it’s Americans you meet here at their summer homes.
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New Hampshire
Now on to the White Mountains. They are in New Hampshire, whose surroundings I find even more impressive than the Maine regions we’ve seen. New Hampshire consists largely of forests, and so we drive for a long time past trees, trees, and more trees. Just before arriving in Jackson, where my chosen accommodation is located, the charming The Inn at Whitney’s Farm, it suddenly goes up and up and down again. The Hurricane Mountain Road, winding through tight curves, gives us a first glimpse of our new home.
Jackson and the White Mountains
And here we are, in the most beautiful ski resort in the middle of summer. After New Milford, this is the biggest idyll on this trip. Instead of being in the forests of Connecticut, we’re surrounded by dense forest and mountains up to 6,288 feet high. Once again, we admire pretty wooden houses in the classic American style with tidy front yards. We also find various restaurants with hearty cuisine here. A place that stands out in many ways and must be mentioned here is the Christmas Farm. It’s worth it just because you can celebrate Christmas here all year round. By the way, I also had the first complete (and best so far) lobster of my life here. I also highly recommend Yesterday’s. We had breakfast several times in the charming diner, which once again satisfied my craving for a real Luke’s.
If you’re traveling with children, you should add this highlight of the area to your to-do list: Storyland. The amusement park brings many children’s stories to life, including Alice in Wonderland, the old woman who lives in a shoe, and many others. There are also numerous rides like water slides, carousels, roller coasters, and a pirate ship. The highlight for my daughter, however, was clearly meeting a real Cinderella in her castle.
From this truly enchanting New England town, which I warmly recommend, we head back to Boston. Once again, with “avoid highways” set, the route takes us over winding roads and through forests back to the urban hustle and bustle. One last tip for lovers of American diner culture before we arrive: the Agawam Diner in Rowley. The silver trailer turned nostalgia diner with its red leather booths offers not only classics like mac ‘n’ cheese, burgers, and more. Even mini jukeboxes on the tables are part of the inventory.
If you have a little more time, you should definitely look around south of Boston: Providence, Martha’s Vineyard, Nantucket—there are plenty of places nearby worth visiting. And if you have even more time, just keep going to New York City and see plenty of Connecticut along the way. Anyway, this New England road trip is, of course, just one option and can be expanded in any direction.
Should You Travel to the USA Right Now?
This question can really only be answered by each person individually, given the dire political conditions, heated atmosphere, and sometimes inhumane injustices. Personally, I probably wouldn’t have flown to the U.S. at this time if it weren’t for a close friend’s wedding. At the same time, I’m infinitely glad we took this trip and got to discover all these places.