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11 Unexpected New England Vacations for Families

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New England is loaded with wonderful places for a family getaway. Popular spots like Boston and Cape Cod are terrific, but the region is also filled with vacation gems that are not yet well-marked on the tourist map. 

The following eleven destinations fly lower on the traveler’s radar and offer family-friendly fun without the overwhelming crowds. 

Strawbery Banke Museum; Courtesy Strawbery Banke Museum

1. Portsmouth, NH

This compact city is a paradise for pedestrians. Stroll the streets and shop the array of independently owned businesses including G.Willikers, a toy store filled with fun and educational games. RiverRun Bookstore has an inviting children’s section with a cozy book nook. 

Strawbery Banke Museum is the city’s pride and joy. This 10-acre outdoor living history museum is an interactive journey back in time. Traditional craft-making opportunities and costumed role-players bring the past to life. It’s open seasonally and during some holidays.  

Prescott Park is a welocme green space. The park’s calendar is clustered with happenings including live concerts, plays and food festivals.

Portsmouth’s Music Hall is a venerable theater that hosts many artistic events, including a series of kid-friendly concerts and plays. Bargain ticket prices and afternoon showtimes make this venue a winner.

Where to Stay: Wentworth By the Sea, A Marriott Hotel & Spa, presents gracious style and luxurious perks. Though it feels like a resort, this historic hotel is just minutes from Portsmouth’s best in-town attractions. Spacious room configurations allow plenty of room to spread out. Kids should enjoy the large indoor pool, seasonal outdoor pools and flower-filled grounds. 

The New Bedford Whaling National Historical Park; Courtesy The New Bedford Whaling National Historical Park

2. New Bedford, MA

New Bedford‘s waterfront is America’s number one commercial fishing port. 

The city is home to the New Bedford Whaling Museum, the largest museum in the country devoted to the story of whaling and local seafaring traditions. A visit provides an in-depth look at the whaling industry’s fundamental place in this town’s history and development. The museum’s galleries include five complete whale skeletons and the world’s largest ship model, which you may climb aboard and explore its nooks and crannies.  The robust family programming component succeeds at keeping the museum relevant for children of all ages. 

The New Bedford Whaling National Historical Park is spread over 13 city blocks. It commemorates the city’s heritage as a preeminent whaling port during the 19th century. It’s staffed with helpful park rangers and screens a free short film on the city’s history several times daily.  

Teenagers with a literary interest will find a stop at the Seamen’s Bethel worthwhile. This simple church was built to bring a dose of morality to the rowdy sailors and whalers before they shipped out to sea. Author Herman Melville was inspired to write Moby Dick after listening to the sermons here. 

Where to Stay: The Fairfield Inn & Suites by Marriott is clean, comfortable and within walking distance to nearly everything.  The free buffet breakfast is a winner, the small indoor pool a refreshing diversion.

Eric Carle Museum of Picture Book Art.; Courtesy Seth Kaye Photography

3. Amherst, MA

Amherst is a quintessential New England college town with bookstores, an indie movie theater and a verdant town common. 

Kids will be over the moon visiting the Eric Carle Museum of Picture Book Art. Founded by the renowned author and illustrator of the classic children’s book The Very Hungry Caterpillar, it’s the first full-scale museum in the country devoted to picture book art. The highlight is the supply-rich art center, where museum educators provide an encouraging environment to create your own art.

The 11-mile Norwottuck Rail Trail is flat, paved and car-free.  Rent bikes or roller blades and pedal a few miles or the entire length.  

Where to Stay: The historic Inn on Boltwood‘s 49 rooms offer modern amenities sprinkled with Colonial charm. Public spaces are inviting, with a blazing fireplace in the well-stocked library.

Billings Farm & Museum calf with kids; Courtesy Billings Farm & Museum

4. Woodstock, VT

Woodstock is a vintage Vermont village overflowing with Green Mountain charm. Residents catch up on local news the old-fashioned way, via the Town Crier, a big chalkboard located near the village green.

Don’t miss a visit to the Billings Farm & Museum. It’s a fully operating Jersey dairy farm where you can get up close with the cows at the milking barn and explore the 19th century farmhouse and creamery. There’s fine educational programming. 

F.H. Gillingham & Sons is Woodstock’s general store, owned and operated by the same local family since 1866. They sell an eclectic range of goods, with quality and craftsmanship being the unifying factors. Local cheeses and maple syrup make excellent souvenirs.

Where to Stay: The Woodstock Inn has 142 spacious rooms and suites. Locally made flannel blankets and tea and home-baked cookies served each afternoon are thoughtful touches.  

Bennington Battle Monument; Courtesy Bennington Battle Monument
Bennington battle monument

5. Bennington, VT

Bennington sits in a cozy corner of Southern Vermont. Its vibrant downtown is filled with mom-and-pop businesses. Those with a sweet tooth have struck gold; the Village Chocolate Shoppe sells mouth-watering classic confections like butter crunch and fudge. Its Avalanche Bars, a combination of coconut, marshmallow and chewy caramel, are memorable.

Though modest in size, the Bennington Museum is home to the largest public collection of works by Grandma Moses anywhere in the world. A visit offers the visual stimulation of her kid-friendly folk-art paintings, as well as the complementary Grandma Moses Schoolhouse exhibit. This re-creation of a 19th century one-room schoolhouse gives kids a window into what it was like to attend a small-town school many years ago. If you feel like going for a stroll, the short and sweet George Aiken Wildflower Trail, adjacent to the museum, showcases native wildflowers and ferns.

Constructed in local limestone, the Bennington Battle Monument is Vermont’s most popular historic site. It was built to commemorate the 1777 Battle of Bennington, a significant turning point in the Revolutionary War. Head to the top of this 306-foot tower and get a tri-state view of New York, Massachusetts and Vermont.

Literary fans, take note: Robert Frost is buried in Old Bennington, where you can visit his gravesite behind the Old First Church.

Where to Stay: Spacious rooms, free Wi-Fi and a hot breakfast buffet with fresh-baked waffles are just a few of the Hampton Inn, Bennington’s perks. It’s located minutes from all attractions. 

The Amazing World of Dr. Seuss Museum. ; Courtesy The Amazing World of Dr. Seuss Museum.

6. Springfield, MA

This former industrial city’s thematic museums should delight children. 

There are five museums situated in the Downtown Quadrangle, including The Amazing World of Dr. Seuss Museum. Theodor Geisel, also known as Dr. Seuss, was born here and his hometown museum is a tribute to his unique role in revolutionizing how we learn to read. The many personal artifacts draw a rich portrait of the inventive man behind these clever rhyming stories. Galleries are highly interactive with an emphasis on merging art and literacy with many opportunities to draw and paint.  Giant bronze sculptures of Seuss characters, including the Grinch and the Cat in the Hat, can be enjoyed at The Dr. Seuss National Museum Sculpture Garden.

Sports fans flock to Springfield to visit the Naismith Memorial Basketball Hall of Fame. Basketball was invented in Springfield in 1891, when harsh winter conditions prompted gym teacher James Naismith to devise an active indoor game to help his students expend pent-up energy. This three-story spherical building is dedicated to promoting, preserving and celebrating the sport. State-of-the-art digitized exhibits let you shoot hoops, refine your passing skills and measure your vertical leap.  

Where to Stay: La Quinta Inn & Suites by Wyndham offers easy access to Springfield’s most popular attractions. Rooms are clean and comfortable. Free parking, complimentary full breakfast and an indoor pool are perks. 

kids learn at the Meigs Point Nature Center; Courtesy Connecticut Office of Tourism
Hammonaset State Park, Meigs Point Nature Center,Madison, Connecticut

7. Madison, CT

Madison is located on the Connecticut shoreline, midway between New York City and Boston. The village enjoys a classic New England ambiance and some of the least utilized beaches on the entire Long Island Sound. 

Hammonasset Beach State Park, Connecticut’s largest public beach park, offers two miles of sandy beach. There’s family programming at the Meigs Point Nature Center, public restrooms, camping and lifeguards in summer. The relatively shallow waters usually stay warm at least through September, if you fancy a late-season swim. 

Boston Post Road’s stores offer excellent shopping and one of the best independently owned bookstores on the East Coast, R. J. Julia. Their children’s collection is large and features New England authors.  

Madison’s Sculpture Mile is an outdoor public art installation. The open-air setting is an easy way to introduce children to art in an informal manner. 

In summer, pack a picnic and head to the picture-perfect Madison Green for a free early evening concert.  

Where to Stay: At the Madison Beach Hotel, Curio Collection by Hilton, rooms have a crisp, nautical feel. Rooms have balconies and views of the bucolic Long Island Sound. The small private beach is delightful. 

Kennebunkport Gooth beach; Courtesy KennebunkportCVB

8. Kennebunkport, ME

For a seaside vacation with a timeless feel, run, don’t walk to Kennebunkport. Nostalgic festivals, yesteryear parades, lemonade stands and lazy afternoons at the beach are on the menu. Its streets are brimming with sweet shops and folksy art galleries.

Kennebunk Beach offers fine beachcombing and a fun playground. 

For the quintessential Maine experience, catch a ride on the Rugosa, a working wooden lobster boat. 

Don’t leave town without savoring a Maine lobster roll from the casual Clam Shack. The hand-picked lobster meat is piled high on a roll with just a dab of mayo or melted butter, proving that simple is sometimes the most delicious. Fried foods, including clams and French fries, should delight hungry kids. 

Where to Stay: The Nonantum Resort has been hosting guests since 1884. It’s the kind of place where guests gather around the fire circle each evening after a friendly game of bean bag toss or a twilight dip in the heated pool. The peaceful grounds include a whimsical fairy garden and dozens of Adirondack chairs sprinkled around the back lawn. 

Westerly Watch Lighthouse

9. Westerly, RI

This corner of Rhode Island is known for its scenic ocean beaches. Surfing, sailing and standup paddle boarding are popular activities. Many hotels offer complimentary loaner bikes, making it easy for families to pedal the gentle terrain and relatively quiet back roads. 

There’s plenty to do beyond the beach. Westerly is a friendly village with restaurants, art galleries and the excellent Granite Theatre. Wilcox Park is a leafy green space with an arboretum and perennial garden. In summer, concerts and live shows are popular park happenings.

Watch Hill, a discreet old-money summer colony, is part of Westerly. Its picturesque lighthouse, old-fashioned carousel and penny candy shop are kid-perfect.  

Where to Stay: The Weekapaug Inn has its own a naturalist on staff leading an array of outdoor activities. The property overlooks Quonochontaug Pond, a body of water larger than New York’s Central Park. Dozens of seaworthy vessels, including kayaks and sailboats, are available. Nightly traditions, such as S’mores by the fire pit, make this hotel a gem for families. 

Newport Cliff walk

10. Newport, RI

This scenic Rhode Island town has been a prominent seaport since Colonial times. The city offers a fine combination of fresh-air activities and cultural attractions. 

Families who like tennis will enjoy visiting the International Tennis Hall of Fame. It recently underwent extensive renovations and new high-tech experiences abound. Highlights include the interactive Roger Federer Hologram, where racket-loving visitors feel as though they are in a room casually conversing with the Swiss champion. The Call the Match exhibit allows you to step in to the role of broadcaster and announce pivotal points.

Built in 1763, the Touro Synagogue is the oldest still-standing synagogue in the U.S. Tours are given throughout the year. 

Cliff Walk is Rhode Island’s most visited attraction. The 3.5-mile path combines natural coastal eye-candy with the manmade Gilded Age mansions. Newport was once the summer playground of America’s richest families, with names like Vanderbilt and Astor among the residents, and their legacy is evident as you glimpse these over-the-top palaces. 

With miles of beaches, exploring the spoils of the sea is practically a requirement. Consider giving surfing a try with the friendly folk at Rhody Surf. The dedicated instructors offer lessons and camps just for kids. 

Where to Stay: Gurney’s Newport Resort is a family favorite. It’s situated on Goat Island, connected to downtown Newport by causeway or a short water taxi ride, so getting there is part of the fun. 

Comfortable rooms, some with water views, are decorated with maritime accents that suit this town’s nautical spirit. The outdoor saltwater pool is a beauty and the large indoor pool is just right for rainy days.

Visitors age 3 to 12 may participate in the kid’s club, offering activities like cooking classes, yoga and visits with the property’s playful live goats. 

Dartmouth College, Hanover

11. Hanover, NH

Home to Dartmouth College, Hanover is an Ivy League town with plenty of activities for kids and their parents. 

The Appalachian Trail cuts right through the village. This simple footpath stretches 2,100 miles, from Maine to Georgia. Venture a short way along the trail to reach Velvet Rocks. This softwood forest is full of moss-covered rocks that look and feel like the plushest velvet.

In winter, the college-owned Dartmouth Skiway is open to the public. It’s a wonderful family mountain, manageable in size with numerous downhill trails for novices. 

On the Dartmouth campus, visit the Hood Museum of Art. Highlights include Peruvian and American folk art and colorful contemporary works of Picasso, Miro and Leger.

Breakfast at Lou’s has been a Hanover tradition since 1947. Grab a roomy booth and feast on hefty portions of eggs, pancakes and decadent French toast made with crullers, served with real maple syrup. They take pride in sourcing locally while keeping prices modest. Breakfast is served until 3 p.m.

Where to Stay: The Hanover Inn graces the Dartmouth Green. The 108 rooms include strategically placed Dartmouth memorabilia, bold splashes of green (the school color) and New Hampshire-crafted furniture. 

Allison Tibaldi is a travel writer based in New York City. With her husband and two kids, she has lived in Rome; Tuscany; Melbourne, Australia; Toronto; and Los Angeles. She studied early childhood development in graduate school and believes that travel is an important part of education. She writes for CNN, TravelChannel.com, HGTV, USA TODAY, Time Out New York, am New York, Family Traveller, Family Travel Forum, Travel Weekly, off Metro and numerous other publications. Follow her @gourmetrav.

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