Nine Must-Visit Stops on a New England Road Trip

Fort Foster in Kittery, Maine. Photo by Miles Howard

One of the many pleasures of living in New England is how very much there is to do in the area, whether you’re interested in Vermont foliage or heading up to Vacationland each summer. And thankfully, all of it is just a short drive away. Road tripping in the area offers abundant opportunities for food, culture, and scenery—all you have to do is figure out what you want to see on your trip. That’s where Boston contributor Miles Howard’s new guidebook, Moon New England Road Trip comes in.

The book, which came out in November, recommends all the classic spots that newcomers would want to see, but with plenty of hidden gems for the seasoned New Englander as well. It’s split into recommendations for both duration of trip and area of interest, whether Boston, Southern Vermont, or Acadia, and has the sort of practical tips that any pragmatic local would appreciate, like an early recommendation to bring more layers than you think you’ll need, because, well, New England.

That buffet of climates and entertainment options is all part and parcel of what Howard says makes New England such a fun road trip destination: “There’s just an incredible diversity of environments and cultures. In the span of just a couple of hours, you can go from a city steeped in 17th century history and beyond like Boston to coastal woods in a place like Arcadia or midcoast Maine, or artist enclaves in the Berkshires or the mountains of Southern Vermont.”

Seeing as he’s now traversed roughly the entire region (he estimates having hit “well over 700 miles” in the course of research), Boston checked in with him to get some tips from an expert on where we should be road-tripping next year. Here’s what he recommends.

The best off-the-beaten-track Massachusetts destination

I’ve really been crushing hard on the Pioneer Valley since being on this book—defining that as the Connecticut River Valley from Springfield, Massachusetts, in the south to Greenville up in the north, and all the towns in between like Northampton and Amherst. Unbelievable scenery, incredible hikes with trap rock cliffs that are really severe and scary right in there. There are also amazing waterfalls and bird sanctuaries out there. And the best bread I’ve ever eaten in Massachusetts, straight from Hungry Ghost Bread in Northampton—that alone draws me out there for repeat visits.

The “unsung hero” destination of New England

One of my absolute favorites, where I spent a lot of time in childhood due to having some family friends up there, is the Northeast Kingdom. This is a part of Vermont that very few people visit, comparatively. The way I would describe it is almost like an agrarian, Nordic-looking utopia in some way. It’s this odd marriage of rolling green hills, where you’ve got cows and sheep grazing, these boreal forests with streams and waterfalls trickling through them, tons of dirt roads. Up in the kingdom, it’s said that you’re not really in the kingdom until you’ve left the pavement behind. Simply driving or biking or walking around is worthy of a trip up there. But then on top of that, some of the most renowned craft beer in the world, from places like the Hill Farmstead Brewery, is located up there nestled in the hills. There are amazing ponds for swimming—very easy to access, too.

And one of my favorite things in the Northeast Kingdom is Bread and Puppet Theater, which is a troupe of giant puppeteers that perform these amazing circuses in this grassy outdoor amphitheater out there. Not only are these performances a delight, but there’s usually a sociopolitical subtext in them as well. Bread and Puppet has appeared at events like the Vietnam war protests. So it’s very much activist art, and you’re seeing it in this unbelievable bucolic venue that feels a million miles away from the city.

Emerald Neckplace photo by Miles Howard

What you should do with only one day in Boston

I would tell you to start with the Boston Common, and then from there take the Emerald Necklace going south—the original linear park system that Frederick Law Olmsted designed right here in Boston. Use the Emerald Necklace as your pedestrian or cycling highway to see some of Boston’s most superlative destinations. You can go right by Fenway Park, the Museum of Fine Arts, you’ll go right by the Comm. Ave. mall and get to see historic housing and Back Bay. You can dart into a shop here and there, maybe grab a bite to eat, and eventually you’re going to wind up in Jamaica Plain. And that’s the home of the Necklace’s arguable gems—Jamaica Pond, Arnold Arboretum, and Franklin Park. And the reason I really like to put an emphasis on this is because not only does the Emerald Necklace happen to pass by a lot of Boston’s most renowned historic sites, but it’s a really rare example of the outdoors and the urban almost seamlessly meshing. That quality, plus the immense walkability of it, is one of the most unique benefits of Boston, relative to other U.S. cities.

The most eye popping sight in New England

I have to say the construction of the hiking trails in Acadia National Park is on a level that I don’t think anything else in New England can quite approach, when it comes to the placement of these paths through unbelievable colonies of moss and flowers, the ornate construction of all these beautiful stone stairs that take you up mountains. Even the ways in which some of the trails use iron bars to help you get up to high viewpoints. It is just an unbelievable feat of engineering that looks like it fits seamlessly into the natural landscape. This unbelievable meeting of the mountains and the ocean. I’ve lived here for almost 30 years and every time I go there, I’m left in awe of it.

The best beach in New England

In Maine, there is an island called Vinalhaven, which is the home of Maine’s largest lobstering fleet. It’s an unusual destination, where as a traveler, you don’t feel like you’re part of a wave taking over the town—you feel like you’re joining the town, more so. On Vinalhaven, there is an island called Lanes Island connected to it by a little land bridge, and the trail around Lanes Island visits a secluded cove, which is one of the most serene places I’ve ever seen in New England. It reminds me of something out of Wes Anderson’s Moonrise Kingdom. And there’s a great big grassy quad for picnicking right there. It’s flanked with all these tall spruce trees. And the tide pooling is pretty outstanding there as well.

The museum you have to visit

One of my favorite finds on the museum front is in a strip mall in Portland, Maine, and it’s the International Cryptozoology Museum. If you grew up watching the X-Files, if your imagination has been sparked by tales of the Loch Ness Monster or Bigfoot, you have to go there, because this is basically a shrine to all of those legends and includes everything from supposed archival footage of creature sightings throughout the world to replicas of legendary monsters. Like, there’s a monkey with fish scales in there. It’s the sort of place where, on the one hand, you’re going to encounter really interesting people, and on the other, you’ll come out of there with this feeling of uncanny valley, that you’ve just seen something you’re not quite supposed to see. I was really amused upon learning about the entire thing, and I was just enthralled upon walking through the doors. And as an added bonus, one of the best craft breweries around, Bissell Brothers, is right next door. So you’ve got yourself a really solid afternoon there.

The best non-Boston, non-Portland food town

Providence, hands down. When it comes to the quality of the food there, the inventiveness, as far as what chefs are doing there, and the price point, it’s really something. I’ve had incredible dinners in Providence for under $20 on multiple occasions, and the international diversity of what’s being served there is really something, too. Many people know that Providence is renowned for Italian cuisine, but I’ve had incredible East Asian-inspired tapas there. One of my absolute favorite Latin American restaurants is a Peruvian joint called Los Andes. I’ve had some incredible baklava from a little bakery called Aleppo Sweets. Providence is the kind of city where you can pretty much walk right into any given restaurant and chances are, you’re going to come away with a mental post-it to recommend this to everyone you know.

The festival you can’t miss

I would be remiss not to mention the WaterFire festival in Providence, because I don’t know of any other event in the US where you can walk by a city river lit by torches, sipping a glass of Pinot Noir with new age music playing from speakers. To give geographic diversity here, I would highlight the garlic festival in the Bennington, Vermont area. Many people in Southern Vermont grow their own garlic, and the Garlic Fest is basically a showcase of their labor first and foremost, but there are many other elements to it, like great home cooking.

And the best lobster to be had in all of New England?

There’s a place in Acadia called The Travelin’ Lobster. It’s lobstermen-owned and run right there. It’s a really bare bones, borderline shack right on the side of one of the roads on the central area of Mount Desert Island. The quality of the lobster I’ve had there, and the steamers, the price point, and just the sheer friendliness of the people running the place and the fact that it’s rarely swamped by travelers, too, means it’s really classic salt of the earth Maine to me. But if you’re in Acadia and you want to get lobster as directly from the sources as you can, Travelin’ Lobster is your best bet.

Moon New England Road Trip is available at local bookstores now.