5 Weekend Road Trips in New England

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New England is home to beautiful, historic coastal towns as well as amazing mountains with plenty of skiing options—the best of both worlds! So, whether you’re planning a weekend trip in the region during the hottest months of summer or the snowiest days of the year, we have you covered with five great road trip options for the perfect weekend getaway. Just save a lobster roll for us, please!

The White Mountains, New Hampshire

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Beautiful fall foliage, great camping in the spring and summer, and a wonderful skiing spot come wintertime—the White Mountains are an obvious pick! There are very few destinations that provide diverse attractions year round and this is one of them. If embarking on a trip full of outdoor activities is your thing, you’ll find yourself right at home. Waterfall views, hiking, fishing, swimming, and kayaking—need we go on? Though there are a few different lodging options, we recommend setting up in one of the area’s campgrounds if you visit during the warmer months.

Montauk, New York

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Located on the tip of Long Island, Montauk feels worlds away. We know Montauk isn’t technically part of New England proper, but it’s an easy travel destination from many spots in the area so it’s worth a mention. Though it’s nearby the posh and expensive Hamptons area, Montauk boasts a more casual, relaxed vibe than its neighbor. Surfing, visiting the famed Montauk Point Lighthouse, or simply sunbathing should all be part of your itinerary. If you can swing it, stay at The Montauk Yacht Club for a relaxed yet indulgent stay. The hotel is impeccably designed with nautical charm and right on the water—best of all, amazing food options are never far when you’re ready for a local seafood fix.

Ogunquit, Maine

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Ogunquit is a seaside town in the southern part of Maine full of beautiful shores, art galleries, and more amazing seafood then you’ll be able to eat. A seasonal destination, we recommend going from June to August for the best weather. More adventurous types will love whale watching and deep-sea fishing; those looking for a slower pace can opt for gallery hopping or good old-fashioned beach time. As far as lodging goes, we recommend staying in one of the area’s many quaint bed and breakfast properties. Regardless of what you do or where you stay, be sure to stop by the Lobster Shack for one of the area’s best lobster rolls (a favorite Maine tradition!).

Stowe, Vermont

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Located in Vermont, Stowe is a mountain lover’s retreat. A small town with a miniscule population, tourism and travel is what the area is known for. And for good reason: Stowe is a truly classic ski resort area you’ve always dreamed of (or at least seen in movies). There’s a cute Main Street with a number of surprisingly good restaurants and bars, but skiing is where Stowe really shines. But also think about a visit in the summertime as there are a number of great hikes and scenic areas to experience during warmer months. The Stowe Mountain Lodge is a favorite hotel option when visiting.

Boston, Massachusetts

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It seems like a given, but how could we not include Boston? The cobblestone streets, art scene, and sheer history of the city make for a perfect weekend getaway. The city is very walkable (except during a blizzard, of course!) so it is fairly easy to get around. Boston has a good amount of food and nightlife options, but we think history buffs will appreciate the city the most. Our pick? Begin your day at Flour, arguably one of the city’s best bakeries, and then head toward the Freedom Trail, a journey that takes you to 16 of the most historic sights in American history. Finish your day with a meal at one of Boston’s fabulous eateries (we love Eastern Standard). Fenway Park and the Museum of Fine Arts are two other essentials to visit as you round out your trip.

  • Eden

    Portland Maine is another great location! Just about 1.5 hours from Boston, but feels worlds away! There is a walk able downtown with great shops, restaurants and coffee shops. Try Duckfat for lunch and Eventide Oyster Bar for Dinner. There are also a bunch of breweries in the area for tastings Shipyard and Allagash just to name a few!

    • Thanks for your suggestions! Great list 🙂

  • Georgia Rojas

    Love NH,ME & MA! Lived in Wolfeboro, NH – adorable town on beautiful Lake Winnipesaukee. Try to visit there and Ogunquit every summer ❤️

  • MeganStetzel

    Some really great options here! Add Martha’s Vineyard to the list! It includes a ferry trip but is well worth the extra mode of transportation! With beaches, hiking, and beautiful little towns it has something for everyone in the summer!

  • All of these places are great! I grew up in Maine and LOVE Portland. It should definitely be on this list. It’s so much fun exploring the Old Port and Boston is only a couple hours away. When I’m home visiting, I take the train into Boston to visit friends. Maine has just about everything, especially if you love the outdoors! The mountains are gorgeous any time of year. There are tons of swimming holes up there and campgrounds. Stowe is gorgeous in the fall. I was never a huge fan of Vermont, unless it’s Autumn. Then you have the beautiful foliage, country stores, apple cider, and apple picking. It’s perfect 🙂 Love New York too, although it’s not part of New England.

  • I would love to take a trip up to New England. My friends who have been there say it’s so beautiful–and it definitely looks that way here!

    Sunday Brunch

  • Explorer9

    The New England recommendations are beautiful. For someone familiar with both areas (including LI), Montauk should not have been included. So many New England options. Acadia National Park in ME. Looking for posh? Check out the mansions in Newport, RI. Other posters mentioned Martha’s Vineyard.

    • megs283

      I agree! I know it’s nitpicky since it’s the same general region, but NY is not New England. Other ideas are the Cape, Mystic Seaport in CT, and Block Island in RI. Or the Berkshires in Mass…

  • Being from NH I am educated on this topic. I grew up going to Ogunquit, ME and can attest that is the a WONDERFUL spot. You must go to Barnacle Billy’s if you really want the true flavor though. Boston needs no explanation with endless possibilities for weekend activities. And I can’t wait to stand in my best friend’s wedding at The Mount Washington resort this fall. Overall, this is a great comprehensive list. If you are looking for other options, the Lakes Region of NH has some of the cleanest and nicest lakes in the country. I may live in Chicago, but NOTHING beats New England 🙂

  • Nicole

    I grew up in western Massachusetts and I currently live in Boston. I absolutely love it. So much history and I could walk the Freedom Trail over and over again. The North End is a must-visit for their Italian food. The Seaport district is up and coming with great restaurants, too.

    I would add Block Island (off Rhode Island) to this list. It’s a cheaper destination than MV or Nantucket and a great island you can bicycle on.

  • Janelle

    Martha’s Vineyard, Cape Cod, Nantucket are great ones too

    Also, New York isn’t part of New England.

    New England is a region located in the northeast corner of the USA. The region is made up of six diverse U.S. states: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island and Vermont.