Backyard Road Trips

Family Getaways within Three Hours of Boston

Living in New England, many regions are just ripe for exploration, whether with kids in tow, as a couple, or even for solo travel. Since the vast majority of the adventures I go on are with the whole family, we’re going to focus on family getaways. Using Boston as our starting point, here’s a list of family getaways within three hours of Boston. No real hidden gems here, just fun family vacation destinations. 

North Conway, NH

The North Conway railroad station.

There’s a reason that North Conway is one of the premier family getaways north of Boston. This town has everything families need to enjoy a vacation. North Conway has it all with a slew of lodging accommodations, plenty of restaurants, and fun activities, such as mini golf, train rides, and ice cream shops. Of course, most travelers use the town as a base for a week of fun in New Hampshire’s White Mountains. With proximity to hiking trails, both for the novice and the professional, and kiddie-themed amusement parks, many of your days will be spent out and about in this area. 

Quechee, VT

In the heart of Quechee

Another one of my favorite family getaways within three hours of Boston is Quechee and the Upper Valley of Vermont. Although less action-packed than the White Mountains, there is still plenty to do here. Quechee itself has the Quechee Gorge Village with shops galore. Get all your moose and bear trinkets, stop in for some Cabot cheese, and pet an alpaca or two. The Quechee Gorge hike is steep but still accessible for kids, with a wide path and gorgeous views. Nearby Woodstock is always a hit and so is the Montshire Museum of Science in nearby Norwich, Vermont. With plenty of dining and lodging options here, check out Quechee and the rest of the Upper Valley for your next family vacay. 

Stowe, VT

A view of Stowe from the Rec Path.

The farthest destination on our list of family getaways within three hours of Boston is Stowe, Vermont. Stowe is not just a winter sports wonderland but is perfect for all seasons. With lots of outdoor adventure, check out the Rec Path or a waterfall hike. With delicious dining destinations and family-friendly breweries such as The Alchemist and Idletyme Brewpub, Stowe’s a hit for everyone. Nearby tourist attractions, including the Ben & Jerry’s Factory and Cold Hollow Cider Mill, as well as the city of Burlington, make it a great focal point for a week away in this region of the Green Mountain State. Of course, if you’re into skiing, Stowe is already on your list. 

Mystic, CT

Mystic Seaport

The small town of Mystic packs such a great family-friendly punch to make this destination a must on the list of family getaways within three hours of Boston. For families, both the Mystic Seaport Museum and the Mystic Aquarium are all-day activities by themselves. But there’s so much more! Downtown Mystic has shops galore, and if you haven’t dropped from all the shopping, check out Olde Mistick Village which is a recreated village (including a church and millpond) full of specialty stores. Nearby, Stonington Borough is a quieter retreat but just as quaint. Check out the surrounding towns, including Groton, Waterford, and Stonington, for beaches, art galleries, lighthouses, and seafood shacks. Fun fact: the village of Mystic is both in the towns of Stonington and Groton. In the fall, check out Clyde’s Cider Mill in Mystic. 

Cape Cod, MA

The windmill is a classic image of Cape Cod

Another incredibly popular family getaway destination but with good reason! Instead of focusing on one town, it’s a whole region and one of the most popular summer vacation destinations in the country. The Cape, as it is colloquially known, has it all. For kids, it’s mini golf, the beach, and ice cream cones. With restaurants aplenty, each town has its vibe, from tranquil Route 6A, winding from Orleans to Bourne, to honky tonk Route 28 in towns like Yarmouth, Dennis, and downtown Hyannis. Chatham and Falmouth are classic New England seaside towns, very attractive with plenty to do. Check out the amazing beaches of Cape Cod National Seashore. And at the very tip of the Cape, Provincetown is a world by itself with shopping, restaurants, and a flourishing arts scene. 

Portland, ME

Portland Head Light

Only about two hours away from Boston is Portland, Maine. Portland is a thriving small city that seems to transform itself based on who is visiting. Whether for a guys’ weekend or a family vacation, Portland is a must-visit city in New England. When I’m with my kids, I’ll still stop by family-friendly breweries such as Bissell Brothers or Maine Beer Company in nearby Freeport. but I tend to tailor the trip primarily for the kids. This means the Maine Children’s Museum, catching a Portland Sea Dogs game, and romping around the Eastern Promenade park. Other family fun include trips to the Portland Head Light in Cape Elizabeth and visits to the L.L. Bean flagship store in Freeport. 

For families in New England, so many, varied destinations are only within a few hours of each other. In this case, these family getaways within three hours of Boston include adventures to Connecticut, Vermont, New Hampshire, Maine, and Cape Cod. None of these are surprises but they are sure to leave the whole family with an experience of a lifetime. 

For longer articles about each destination, make sure to click the links in the text.

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