A Week-long Road Trip on the New England Coast

Road trips are probably my favorite way to travel. I love the way the world blurs at 60 mph and I love how you get a much better sense of distance when you go somewhere in a car versus taking a plane. Also, you get to see all the rural bits of America between all the major cities, which can be pretty educational.

My general approach to road trips is variety. I like my road trips to visit big cities, rural towns, plenty of backpacking or hiking, and usually a National Park or two. This New England road trip hits all of those points and so much more. There’s also a nice educational bit to almost every destination along the way. New England is where America started and there’s so much history here. I’ve actually linked a couple articles and books set in some of the locations so you can learn while your travel. Additionally, we try to keep road trips pretty affordable, so we usually do a combination of camping and hotel stays to keep costs down.

This particular road trip along the New England Coast is a favorite of mine because I had never really spent a lot of time in New England and, growing up in Texas, I had a lot of false assumptions about the place. I thought that New Englanders would be rigid, unfriendly, and snobby and I thought the nature would pale in comparison to the beauty of Texas and California (where we were living at the time). Boy was I wrong.

We started in bustling New York City because flights to the city are cheap from almost everywhere in the country. I also love a giant metropolis from time to time. Next, we headed north to the Storm King Art Center, an expansive outdoor museum with an impressive collection of ginormous art. After that, we turned east and drove along the Connecticut coast on the way to Cape Cod in Massachusetts. Of course we stopped for pizza multiple times along the way.

We spent a couple days camping and eating seafood in Cape Cod and then headed to the next big metropolis, Boston. In Boston, we strolled the Freedom Trail, lurked in the corners of ancient pubs, and basked in all the history of the town. To finish out our road trip, we headed far far north to Acadia National Park.

In Acadia, we hiked along the coast; we hiked along the lakes; and we hiked up the mountains. We also had one of the best plates of fancy nachos ever in Bar Harbor and saw the sun rise over the Atlantic on the very last day. Oh, and we ate all the wild blueberries and lobster we could find. Then we drove back south to Portland and caught a plane back home.

Number of nights: 2

Average hotels price: $180

We started our road trip with New York City because it’s inexpensive to fly here (they have three airports nearby), easy to get a cheap rental car, and it’s a pretty fun place. Even though I’ve been to the city a couple times (Dylan’s parents live nearby), I still feel nervous and excited every time we visit.

In the city, we tend to spend most of our time wandering around without much of a plan. The world-famous landmarks like the Statue of Liberty or the Metropolitan Museum of Art, are probably worth a visit, but New York City is so big that I think the best way to get the most out of your visit, is to follow your own interests instead of running from landmark to landmark.

As you’ve probably guessed, we like to be around nature and we really like walking long distances. That’s why we treat our days in New York City like urban backpacking trips. We throw a bunch of essentials in a backpack, like extra clothes, my camera, and a two water bottles, and hit the streets. We also tend to wander around green areas like Central Park or the High Line or historic-looking neighborhoods like SOHO.

Beforehand, I map out an approximate route on the running app, Strava, so that we have an idea of walking distances and so we don’t get stuck along the way (and develop decision fatigue) trying to decide which part of the city to walk towards next. Of course, if we walk past an enticing alley that deviates from the route, we’re always going to check it out.

For food or drinks, we just Yelp or Google a restaurant whenever we get hungry or thirsty. It seems like no matter where you are in the city, you’ll be able to find really really good food because restaurants here need to be good to stay open. It also feels like every popular place we want to try, like Katz’s Delicatessen, always has a line around the block – and we don’t really like waiting in lines when we travel. If there’s something we definitely want to eat (lines be damned), I’ll plan our route on Strava around the specific restaurant or bakery.

Number of nights: 1

Average hotel price: $90

Storm King Art Center is what happens when a giant makes some art and then delicately places it all over a bunch of perfectly manicured lawns. It’s super fun, kind of disorienting, and even enjoyed by people who aren’t that into art. After touring the art and earning all your steps for the day, you can snack on an apple cider donut at nearby Jones Farm & County Store. The County Store is also full of homemade jams, an impressive collection of baked goods, and classy-country-rural kitchen decorations. They also have horses and chickens outside because it’s a real-deal farm too.

This is a pizza stop, plain and simple. If you like giant, floppy slices of thin-crust New York style pizza, wait ‘til you try the pizza at Frank Pepe Pizzeria Napoletana. Frank Pepe’s serves New Haven-style pizza, which is a thin-crust, coal-fired Neapolitan pizza — and it’s extremely tasty. The people who work here are also pizza pros. They fling and slice pizzas with extreme efficiency and it’s pretty entertaining to watch.

This is sort of another pizza stop, but Mystic is so much more than tasty pizza. Mystic is a small town on the Connecticut coast that really rises to the occasion of being an adorable coastal town. It’s got all the things you would expect in a touristy seaside town but everything is impeccably designed. It’s got a drawbridge, a knot store, a harbor full of sailboats, countless maritime themed restaurants and bars, and that crisp seaside architecture. Dylan and I were obsessed with the simply painted white houses with black trim and all the perfect yards.

Oh and Mystic Pizza from that Julia Roberts movie is located in town and their pizza is fluffy-crust, burnt-pepperoni perfection. The pizza here earns the coveted title of My Favorite Pizza in the World.

Number of nights: 2

Background reading: Cape Cod by William Martin, historical fiction

Cape Cod reminds me of childhood summers, the Fourth of July, patriotism, and the kind of luxury that’s not fussy or showy. Driving up the cape, you’ll see giant fancy houses, next to nondescript strip malls, next to colorful mini-golf centers. In the early 20^th century, when the Cape was really getting developed, the current residents fought hard against the strip malls and kitschy tourist shops. They lost, but thanks to their fight, large parts of the Cape survived and retained its old-world, seaside charm.

Number of nights: 1

It’s hard to imagine an American city with more historical charm than Boston. One of the main attractions, The Freedom Trail, is literally a walk past some of the most historic areas in the city — complete with classical American architecture. Besides basking in the history and the museums, you can also lurk in the old pubs around town, take a kayak out on the Charles River, or pretend that you study or teach at the Harvard and MIT campuses.

My one gripe with Boston was how impossible it was to navigate the city by car. Many of their major highways are actually underground because they ran out of room up above. This caused our GPS (Google maps) to constantly lose track of where we were, especially at critical turns. I’m sure the Bostonians know where they’re going, but as visitors, we were struggling not to get lost.

This is the way less famous Portland — sorry Maine! If you want to search up this airport, you’ll actually have to type “Jetport” instead of “Airport,” because “Airport” was taken by the other Portland.

Anyways, this Portland is very nice. It’s historic but not flashy and has great donuts. On our way from Boston to Acadia National Park, we stopped in Portland for quick lunch but ended up spending a few hours walking around town. I also had a delicious blueberry donut at the potato-based donut shop, The Holy Donut. I still tell everyone who will listen about this donut two years later. Also, the blueberries here are of the wild variety, so they’re super flavorful. We also had sandwiches at Market Street Eats and bought some fancy beer from Old Port Spirits and Cigars for our Acadia camping days. If you have some extra time and are into craft beer, Allagash Brewing Company is only 5 miles north of Portland and pretty much on the way to Acadia.

Number of nights: 3

Price of campground: $30/night

If you’re wondering if Acadia National Park is worth the long-distance schlep to this far corner of Maine, you’ll have your answer the second you take your first hike. Not only does this park have majestic coastal scenery, but it also has equally amazing trails around its lakes and domed peaks.

We decided to devote the first day to coastal hiking by connecting a bunch of trails near the Cadillac Cliffs. The second day was for inland hiking when we linked together a couple trails near Jordan Pond. I picked trails that start down low and made us hike uphill to the big viewpoints. On our second day we also headed to the southwest corner of the park to watch sunset at the Bass Harbor Head Lighthouse. As expected, this viewpoint was swarmed with photographers but it was still quite peaceful. Before the lighthouse we stopped at Thurston’s Lobster Pound for some birthday lobster sandwiches (it was my birthday).

On top of all the great nature, the town of Bar Harbor in the northeast corner of the park, is a nice place to shop and eat after all the hiking. In town, there’s plenty of tasty seafood, wild blueberry pie, and enough colorful souvenir shops to satisfy anyone. During low tide, you can also walk across a sand bridge at the north side of town to Bar Island. There’s not much on the island, but it was fun to walk on all the mushy sea stuff on the sand bridge.

The only downside to Acadia National Park? No backpacking. We car camped at Blackwoods Campground the first two nights and Seawall Campground the third night. I liked the first campsite better, but it was nice to have variety.

Thinking about taking a classic New England road trip? Leave a comment down below!