Where To Eat & Drink On Your NYC To Portland, Maine Road Trip

Summer in New York is great, but so is escaping the city’s smells and running away to Portland, Maine: the land of never-ending fresh seafood, lighthouses, and L.L. Bean sweaters. Plus, a road trip to Maine is a lot cheaper than a flight to Japan, and you can stop in cute seaside towns along the way. 

While there are many great spots to eat up the Eastern Seaboard, we’ve found the places that make pulling over actually worth it as you take I-95 all the way up through Boston or meander through Connecticut via more scenic highways. Here are a bunch of options for where to grab a sourdough donut to avoid hanger-induced road rage on I-95, get a drink and fries after surviving Boston-area traffic, and more.

CONNECTICUT

Gold’s is equidistant from I-95 and Merritt Parkway, so it’s a short detour no matter which way your phone’s GPS has you driving through the Connecticut coast. Call ahead to order a super sandwich that’s filled with corned beef, pastrami, swiss cheese and coleslaw, and served with a container of creamy russian dressing and a perfectly tart pickle. When you arrive to pick it up, you’ll definitely want to stock up on the deli’s selection of road snacks like chips, cookies, and more.

If you’re stopping in New Haven, you’ll want to take some time to try the city’s famous Apizza. Sally’s makes the best pies in town with an ideal amount of char on the crust and flavorful sauce, but you’ll need to plan ahead by placing an online order a few hours before your arrival, as they’re always slammed, even on a slower weekday. Once you pick up your pie, you can take a moment to stretch your legs a bit and walk to Wooster Square Park, or just sit on the hood of your car to more immediately enjoy a slice.

Nana’s in Mystic appeals to two types of road trippers: the Type A who wakes up at 5am to beat the morning traffic, and the procrastinator who packs the hour before they leave and doesn’t start driving until noon. The morning folks can grab an egg sandwich and a latte with coconut miso caramel before getting back on the road, while the afternoon stragglers can grab a 13-inch mushroom and creamed kale pie to enjoy outside beside the Pequotsepos River.

You shouldn’t leave without several of their made-to-order sourdough donuts, though, which are perfectly pillowy with a hint of fermented tang, and topped with your choice of dustings like matcha ginger and cacio e pepe.

PROVIDENCE, RI

Is there anything more suited for a road trip than a massive, capocollo-and-pepperoncini-filled sandwich? Probably not, so stop for lunch at this takeout joint in Providence. Sandwich Hut is right off I-95, which makes it a quick pit stop, and the choice of italian subs and parm sandwiches are hearty enough to help you power through a few more hours of driving. 

MASSACHUSETTS

Located just off I-90, Treehouse Brewing in Charlton has lots of indoor and outdoor space, so use it as an opportunity for any pet or child passengers to get their zoomies out. There is a very extensive draft list, so you’ll find something for both IPA lovers and the folks who’d rather go for a lager or pils. If you want to eat while you’re there, they also occasionally have food trucks parked outside on the weekends serving everything from grilled cheese to ice cream.

PORTSMOUTH, NH

Portsmouth is just across Maine’s southern border, and about an hour’s drive from Portland. It’s worth taking some time here to watch boats sail along the Piscataqua River and walk through the scenic downtown area, but if you can only make a quick stop, Nikki’s Banh Mi is the spot to grab a couple of to-go sandwiches.

If you don’t want to risk getting baguette crumbs all over your car, the interior is also cozy enough to enjoy your meal at the counter with a beer or Vietnamese coffee. There’s the option to customize your spice level on the sandwiches, but if you want to skip the baguette altogether, the bánh mì tacos are made with pillowy soft flour tortillas and drizzled with spicy mayo.  

If you’re looking to stretch your legs out a bit and sit somewhere that isn’t the front seat of a cramped sedan for a few hours, take a longer break at Street 360. This international street food restaurant is located in a shopping center just before you get downtown, so there’s plenty of parking available. If you’re road-tripping with friends, make them pay for more than just gas by splitting some subarashii fries that come with both scallion mayo and kimchi ketchup and the bibimbap with crispy sticky rice that’s served in a piping hot cast-iron skillet.

KITTERY

Once you cross over the border from New Hampshire into Maine, you can celebrate being a mere hour away from Portland’s most famous lighthouse by enjoying some of the state’s best fried seafood. Bob’s Clam Shack is by no means some under-the-radar spot. There are signs and placards from various TV shows and “Best Of Maine” list appearances, plus a perennial line snaking out from the order window. But it more than lives up to the hype. 

The crisp and tender fried clams will probably convert your friends who steer clear of anything seafood, and the steak fries that come with seafood baskets or rolls are generously seasoned and have the perfect balance of crunchy exterior and soft interior. Bob’s also makes one of the best lobster rolls in the state—the meat is tender and sweet, and the toasted bun is just the right amount of crispy and buttery.

OGUNQUIT

Ogunquit is a quaint seaside town where you should make a pit stop to check out all the little gift shops, fun bars, and oceanside views—or even consider spending the night in one of the town’s waterfront hotels. Treehouse Taqueria is the place in town to unwind after a long day of driving, and walking up its nondescript staircase feels like arriving at your cool, free-spirited friend’s tropical cabin. The backyard is quiet and has a small fire pit, while the covered patio lets you enjoy the breeze without putting you at risk of baking in the sun. 

Their $20 mix-and-match taco plate comes with options like chicken tinga, birria, and jackfruit al pastor, but the best one is the veggie taco with bright broccoli, queso blanco, scallions, and chili flakes. Sweet, tropical drinks are also tailor-made for enjoying on a lazy summer afternoon, and they also do 32-ounce cocktail buckets for $20 if you’ve been relieved from driving duties. 

WELLS

Congdon’s is a Southern Maine institution, which means it’s more than worth a lightning-fast detour off Route 1. You’ll likely see a line out the door when you pull into the parking lot, but thankfully, it moves pretty quick, so you can enjoy your doughnuts and coffee on the road or in their outdoor seating area.

While their maple-raised donuts are unmatched, get at least a half dozen so you can try their airy raised, filled, or cake varieties with different fillings, frostings, and sprinkles. If you stop by after the shop closes for the day, they convert the large lot into a food truck park with rotating vendors, a beer garden, live music, and car shows.

BIDDEFORD

If you decide to break up your road trip into two days of driving, Palace Diner in Biddeford should be the stop you make on the second day. Go early, since there are only 15 seats available at the train car counter. (If you’re the type of person that sets eight alarms and still runs late, you can always place a to-go order and eat in the nearby outdoor courtyard.)

The dine-in and takeout menus vary slightly, but either way, you should try their fluffy buttermilk flapjacks and the deluxe breakfast sandwich that comes with a thick square slab of eggs, cheddar, jalapeños, mayo, and your choice of bacon or sausage on a toasted english muffin.

If you’ve made it this far, congrats—you’ve arrived in Portland! Make sure to hit up a couple breweries, do some whale watching, or visit a few local shops and museums. While you’re in town, check out our guide to find all the best restaurants for your trip. 

PME Guide

The Best Restaurants In Portland, Maine