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How to Eat (and Drink!) Your Way Through New England

It's time to rev up the engine, roll down the windows and embark on an epic New England road trip. Not sure where to start? We're breaking down the best stops along I-95—as well as where to eat and drink in each town.

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Ralph n Rich'svia

Bridgeport, CT: Stock up on Seafood

Kick off your New England road trip on Long Island Sound, where Bridgeport feels like a breath of fresh air. The town has no shortage of Italian restaurants like Ralph n Rich’s and Trattoria ‘A Vucchella, but you might want to align your trip with Bridgeport’s annual Barnum Festival, a seafood-packed extravaganza.

Hotels in Bridgeport proper are hard to come by, so we recommend browsing through Airbnb’s selection.

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Mystic Pizza in Connecticutedella/Shutterstock

New London, CT: Grab a Slice

Connecticut’s charming town looks like it could’ve been pulled straight out of a movie—and, well, it sort of was. While New London may not be familiar, it’s a hop, skip and a jump away from Mystic (as in Julia Roberts’ movie, Mystic Pizza). Dine to the nines at On the Waterfront, a popular seafood eatery with sweeping views of the Thames River. After dinner, order a pint of beer from The Social’s extensive brew menu.

Don’t forget to head over to Mystic Pizza and grab a slice. Julia would be proud!

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The view of Newport city and the old harbour (Rhode Island).Ramunas Bruzas/Shutterstock

Newport, RI: Uncork the Wine

Newport is a slight detour from the usual route but trust us, it’s worth it. This idyllic town might be famous for its ultra-luxurious houses like the Breakers, but it’s also a great place for a girl’s weekend. Book a stay at the ultra-stylish Gurney’s Newport Resort & Marina.

Newport Vineyards is one of the top places to wine and dine (but mostly wine) in New England. And once you’ve found your favorite blend, pair your vino with some seafood at Kempenaar’s Clambake Club.

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Chatham Decommissioned LighthouseRuss Hamilton/Shutterstock

Chatham, MA: Order Oysters

Is any New England road trip complete without a visit to Cape Cod? We don’t think so. Somewhere in between lounging on the beach at your hotel (we recommend the Chatham Tides hotel) and checking out the iconic lighthouse, slurp down oysters at the Impudent Oyster. Located in an old church, this spot is bound to satisfy your seafood craving.

Before you head back to the hotel and prepare for another day of fun in the sun, spring for a drink at The Chatham Squire, a local pub.

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Juicy-looking burger with bacon and lettucevia

Plymouth, MA: Bite into a Burger

You’ll want to visit Plymouth on your New England road trip. As the site of Plymouth Rock and the Pilgrim Museum, Plymouth is one stop bursting with patriotism. And what could be more American than stopping by a burger joint? With a 4.5/5 rating on TripAdvisor, KKatie’s Burger Bar is certainly worth a stop. Between the Rock Burger, which boasts four quarter-pound patties, and enough beer to go around, KKatie’s is a great place to eat and drink.

If you want to look out to the exact waters the pilgrims sailed into, check into Pilgrim Sands on Long Beach, which has its own private beach.

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Ben & Jerry's ice cream in a cone and dishvia

Waterbury, VT: Order a Scoop of Ice Cream

Looking for a quick pitstop that will satiate your inner sweet tooth? Hop on Route 89 and head over to Waterbury, Vermont. Not only is this quaint town full of hiking trails and reservoirs, but it’s also home to Ben & Jerry’s ice cream factory. If you still have some room after trying all those flavors, stock up on some old-fashioned cocktails and lip-smackin’ barbecue at Prohibition Pig.

Now that you’re in full food coma mode, catch up on some zzz’s at the local Fairfield Inn & Suites. Psst…this hotel is right by the Ben & Jerry’s factory, so you can stock up on ice cream samples before driving away from Waterbury in the morning.

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Welcome to Portsmouth New Hampshire SignSteve Broer/Shutterstock

Portsmouth, NH: Pile on the Meat

Whether touring the USS Albacore or getting wet and wild at the nearby waterpark, Portsmouth promises there’s something for every member of the family. But when it comes to planning meals: Meat, it’s what’s for dinner. Sitting on the Old Harbour, the locally sourced meat at the Black Trumpet is a consistent crowd-pleaser. (Did we mention it was a semi-finalist for a coveted James Beard Award?)

You can grab a pint at the Tributary Brewing to end your day. For that small town charm, book a room at The Hotel Portsmouth.

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Tourism is a huge part of Portland's economy, as cruise ships bring in thousands of tourists to restaurants, bars, landmarks and shopping in the waterfront area.Darryl Brooks/Shutterstock

Portland, ME: Eat a Lobster Roll

Maine is the lobster capital of the United States, so where better to break out the bib than Portland? While the laid-back port city has no shortage of mouthwatering restaurants, the browned butter that Eventide puts on its lobster rolls will have you begging for more. Other highlights include the lobster diavolo at Street & Co. and practically anything at Portland’s Fore Street Restaurant.

Portland’s downtown area is bustling with bars and restaurants, so stay close by at the Portland Regency Hotel.

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Moe's serves up some finger-lickin' good barbecuevia

Bangor, ME: Indulge in Comfort Food

End your New England road trip with a bang in Bangor, Maine. This sleepy town has plenty of tourist attractions, including Stephen King’s house and a massive statue of Paul Bunyan. You’ve reached your final destination, so what better way to celebrate than with some comfort food? And no, we’re not talking about the drive-thrus you tried so hard to avoid. Fiddlehead gives comfort fare an elevated flair while Moe’s serves up some finger-lickin’ good barbecue.

Once you’ve scarfed down all the eats your stomach can handle, unwind at Bangor’s Best Western White House Inn. Then head home and savor all those delicious memories.

Note: Every product is independently selected by our editors. If you buy something through our links, we may earn an affiliate commission.

Kelsey Mulvey
Kelsey Mulvey is a freelance writer and editor based in New York. Her hobbies include wine, nachos and the occasional hibachi dinner.