Best Year-Round Weekend Getaways from Boston

Boston packs a punch in terms of things to see and do, from diving into American history to exploring hip neighborhoods and visiting some of the country’s top universities. What a lot of visitors might not realize, however, is how well situated the city is for a number of top-notch New England weekend getaways. To make the most of your time, extend your stay by a few days and add on one of these family-friendly destinations — all less than 3½ hours away by car, with something to enjoy in every season.

4 All-Season Family Escapes Within Easy Reach of Boston

Kennebunkport, Maine

A mere 90-minute drive north of Boston is the picturesque coastal town of Kennebunkport, Maine. A stroll through this charming town will have you living your best New England life as you take in the lobster boats, sailing vessels, whitewashed churches and colonial-era homes of former sea captains. Indulge in some of the region’s best lobster rolls at The Clam Shack; browse the plentiful boutiques, bookstores, and galleries; and end your day by cooling off with ice cream or warming up with a cup of hot chocolate, depending on the season. 

In summertime, visit nearby Goose Rocks Beach, one of southern Maine’s best beaches. Throughout the spring, summer and fall, consider kayaking on the Kennebunk River, biking along coastal roads, taking a lobster boat tour or harbor cruise, whale watching (mid-June through early September) or deep sea fishing. There are also great opportunities for birdwatching and hiking in the area. Mid-October means peak fall foliage in this coastal Maine town — witnessing the vibrant explosion of colors along the water creates an unforgettable memory.  

In December, Kennebunkport hosts Christmas Prelude, one of America’s best-known holiday festivals. Colorfully decorated lobster trap Christmas trees, horse-drawn carriages and holiday markets bring the season to life in this cozy town. 

Where to Stay

Kennebunkport offers several family-friendly luxury accommodations. If you want a forested setting, great kids’ programming and a number of accommodation options to suite large families or multigenerational groups, we recommend the spectacular, award-winning Hidden Pond. For smaller families or couples looking for a sophisticated, luxe stay, opt for the White Barn Inn. 

Newport, Rhode Island

Less than 2 hours’ drive south of Boston will put you in the sailing town of Newport, Rhode Island. Known for its famed Cliff Walk, iconic Gilded Age mansions, a lineup of year-round festivals, world-class sailing and beaches galore, there is always something going on in this New England hotspot. 

For the full Newport effect, it’s best to visit in summer. Walk Bowen’s Wharf; take a sailing tour (or sail yourself); hit up the Folk Fest, Jazz Fest or Kite Festival (all in July); visit one of the local beaches (our favorites are Sachuest/Second Beach and Gooseberry Beach — both require a visitor’s permit for entry); and indulge in a Del’s Frozen Lemonade, only found in Rhode Island. In the summer, fall and spring, you can stroll along the beautiful Cliff Walk, hike at the Sachuest Point National Wildlife Refuge or the Norman Bird Sanctuary (both are great for families), experience the thrill of a Newport Polo match, visit the Newport Mansions, browse the shops along Thames Street and take the hop-on/hop-off Jamestown-Newport Ferry to explore Rose Island, Fort Adams, Newport and Jamestown by water. 

Newport’s well-kept secret is that the months of September and October are a fantastic time to visit. The ocean is still warm (especially through September), the crowds have dissipated, sailing conditions are generally very favorable and sunsets are stunning. If you find yourself in Newport during the spring, the best time to visit is during Newport Daffodil Days to enjoy the explosion of yellow blossoms lining the beach areas, parks and town center. 

If you visit in the winter, don’t miss the Holidays at Newport Mansions to experience the beautifully decorated estates. Just across the bridge from Newport in Jamestown, there is a full day in early December dedicated to the festive season, during which local artisans sell their handmade crafts, the fire station and vendors along the main street offer hot chocolate and treats to passersby, the local school jazz band and chorus play holiday classics, and the official town Christmas tree is lit. If you want that Hallmark movie-style small-town holiday feel, this is it!  

Where to Stay

For visitors looking to stay along the harbor in a modern, family-friendly accommodation, The Brenton Hotel is a great choice. Prefer a more classic feel? The Vanderbilt, Auberge Collection, fits the bill. Both properties are boutique in nature and centrally located. 

White Mountains, New Hampshire

New Hampshire‘s picturesque White Mountains are only a 2 1/2-hour drive from Boston. This destination shines in all four seasons and offers a huge diversity of activities for families looking to soak up the fresh mountain air, whether on the slopes, in the water or on a hiking trail. 

The Omni Mount Washington is a perfect base from which to enjoy all-season activities. It owns and operates the Bretton Woods Adventure Center, which is the White Mountains’ premier outdoor adventure hub. The center offers gondola rides, zipline tours, mountain biking, disc golf, rock climbing, guided hikes, fly fishing, horseback riding, and golfing in the warmer months. Come winter, enjoy alpine skiing (Bretton Woods has wide, well-groomed trails that work well for families and beginners), Nordic skiing, adaptive skiing, snowshoeing, tubing and more. These activities can be booked individually, whether you are staying at the Omni, at another hotel or just visiting for the day. 

Other activities in the area include hiking the Franconia Ridge (consider hiking the Flume Trail to Flume Gorge in the spring or fall) or Mount Willard; paddling in a serene mountain lake; taking a railway adventure on the Conway Scenic Railroad or the Mount Washington Cog Railway; or, in spring, learning about the production of maple syrup at a nearby farm. I’m sure it comes as no surprise that the mountains of New Hampshire provide one of the most vibrant leaf shows in the country as the foliage changes. Fall in New Hampshire is absolutely stunning, but be prepared for the large crowds of leaf-peepers that descend upon the area.

Where to Stay 

The Omni Mount Washington delivers a treasure trove of wonderful activities for guests in an upscale resort setting, and sits adjacent to New Hampshire’s largest ski area with nearly 500 acres of skiing and snowboarding on 63 trails and 35 glades. Visitors should also consider the Mountain View Grand Resort & Spa, a resort that offers an array of activities for families and has a working farm onsite that is sure to delight the youngest travelers. 

Stowe, Vermont

While it’s the farthest weekend getaway on our list from Boston (just over a 3-hour drive), Stowe is well worth the distance. This luxury village stays active year-round and, like New Hampshire’s White Mountains, delivers a distinctly different experience in each season. The terrain is well suited for confident intermediate skiers, and the charming downtown is full of outstanding restaurants and craft breweries. For families who want exceptional skiing and an authentic mountain town experience, Stowe is hard to beat.

It’s no secret that Stowe’s signature season is the winter, given the number of expert runs, glades and trails it offers strong skiers and snowboarders. Advanced skiers can spend several days exploring the slopes without getting bored. Non-skier? No problem. Snowshoeing, dog sledding, ice skating at the Spruce Peak Village Center, sleigh rides at nearby farms, riding the Stowe gondola or spending a spa day at one of the many luxury Stowe resorts are excellent alternatives. 

In the fall, summer and spring, Stowe transforms into an outdoor playground. Hike miles of trails (try Moss Glen Falls), mountain bike, zipline through the forest canopy or head to the Ben & Jerry’s Factory Ice Cream Shop (it’s only a 20-minute drive) for a sweet-filled tour that is sure to delight all members of your traveling party. In the summer, join the locals and cool off at a swimming hole; in spring, visit local sugarhouses during maple sugaring season. 

Where to Stay

For families or multigenerational groups looking for ski-in/ski-out access, The Lodge at Spruce Peak , a Hyatt Hotel, at the base of Stowe Mountain Resort offers luxury rooms, suites, and residences, an outdoor pool, and a spa and wellness center. If ski-in/ski-out access isn’t as important, the von Trapp Family Lodge is a fun alternative that offers a number of family activities, including a kids’ club. If you are looking for a quieter, boutique-style resort just minutes from downtown Stowe, consider TopNotch Resort. This property places an emphasis on wellness, relaxation and outdoor recreation, and is best suited to families with older kids or couples looking for quiet luxury. 

Relevant Links: 

5 cozy resorts in New England for wintertime fun 

Rhode Island with kids: New England’s most underrated trip

10 fun things to do in Newport, Rhode Island with kids

A year-round retreat: Goose Rocks Beach House in Kennebunkport, Maine

Cozy, eco-chic luxury at Maine’s Hidden Pond Resort

Top things to do on a Boston family vacation

Sink into serene opulence at Four Seasons Hotel One Dalton Street, Boston

Photos by Loren Braunohler except where noted.

Editor’s note: This post was accurate when published. We advise checking independently for the latest information and updates. Ciao Bambino does not accept responsibility or liability for any errors or omissions in, or for any actions taken based on, the information presented.