Not the Woodstock you are probably thinking of, this small town in Vermont contains 3,200 residents spread among five even smaller villages and hamlets. But just because this isn’t the site of the infamous music festival doesn’t mean there aren’t a bunch of great sites to take in.
Where to stay: The Woodstock Inn & Resort, for rustic luxury; the Jackson House Inn, located just outside the heart of the village.
Where to eat: Bentley’s, for delicious food that makes the most of local Vermont ingredients like cheddar cheese; Mountain Creamery, for homemade ice cream; The Prince and the Pauper, located in the heart of Woodstock Village.
What to do: Stock up on fresh produce, meats, and more at the Woodstock Farmer’s Market; experience Vermont farm life at the Billings Farm & Museum; see live music, classic film, and more at the Woodstock Town Hall Theatre.
Block Island, located just over 10 miles off the southern coast of Rhode Island, has only one town — New Shoreham. While the main part of town is located right by the ferry terminal, you can rent bikes or Jeeps to travel all over the island. Though it only has about 1,000 year-round residents, Block Island welcomes up to 20,000 visitors a day during high season. Aside from one Ben & Jerry’s, the island is free of chain stores, meaning it is great for local shopping and dining.
Where to stay: The National Hotel, located in the main part of town; The Old Town Inn, a building originally constructed in 1825.
Where to eat: Winfield’s for an eclectic mix of cuisines; Finn’s Seafood for, naturally, seafood.
What to do: The main part of town is pretty small, so after walking around for a bit, you’ll want to get out to explore the rest of the island. There are two great lighthouses — one on the north part of the island, the other on the southeast; hike along parts, or all, of the 25 miles worth of walking trails for great views of the ocean.
You might recognize Rockport as one of the filming locations of the 2009 film The Proposal. Even if you don’t, this town of under 7,500 residents, stunning in its “quintessential New England seaside village” vibe, should be on your radar. Most people eschew northern Massachusetts in favor of Cape Cod, but Rockport proves why it’s definitely worth heading up from Boston.
Where to stay: Bearskin Neck Motor Lodge, for a location right on Rockport’s main drag; the Seafarer Inn for the B&B experience.
Where to eat: Top Dog for amazing hot dogs; any of the candy or ice cream shops along the Bearskin Neck drag.
What to do: Stroll up and down Bearskin Neck, a small area of land that juts into Rockport’s harbor, stopping in at all the small craft stores along the way; check out The Paper House, a home constructed from actual newspaper; listen to live music at the Shalin Liu Performance Center.
One of America’s original vacation playgrounds for the rich and famous, Newport still retains much of the luxurious charm that made it so appealing to earlier generations. But although the city is perhaps best known for its larger-than-life mansions, it packs plenty of classic New England character as well.
Where to stay: The Cliffside Inn, for a luxury bed and breakfast experience; The Chanler at Cliff Walk, to stay right near the city’s famous mansions.
Where to eat: Rosemary & Thyme, for European-style baked goods; Mooring Restaurant, for a twist on classic seafood and sandwiches.
What to do: Walk along the 3.5 mile Cliff Walk to take in the mansions, including the famed The Breakers; tennis fans should check out the International Tennis Hall of Fame; visit Touro Synagogue, the oldest Jewish house of worship in the United States.
Bar Harbor is a haven for nature lovers, known for its rugged coast and containing the largest parts of Acadia National Park. The town’s name comes from a sandbar revealed during low tide that is used by kayakers and hikers as a launching point for exploration.
Where to stay: The Bayview, for rooms overlooking the water; The Moseley Cottage Inn & Town Motel, originally built in the 19th century.
Where to eat: The Side Street Cafe, for classic comfort food; Two Cats Cafe, where you can purchase cat-themed souvenirs; The Jordan Pond House, for views overlooking Acadia.
What to do: Hike Acadia National Park and take in the views of Cadillac Mountain; learn about the native Wabanaki peoples at the Abbe Museum.
With only about 600 residents, Grafton is the quintessential tiny New England town. It’s a village of strong connections between the people, even continuing to hold traditional town meetings.
Where to stay: The Grafton Inn, for traditional New England charm.
Where to eat: Phelps Barn Pub, for drinks and pub food conveniently located in The Grafton Inn; Mack’s Place Eatery, for cheap and casual salads and sandwiches; Grafton Village Cheese, for…cheese.
What to do: Check out the Kidder Hill Bridge, a classic New England covered bridge; enjoy winter sports like cross-country skiing at Grafton Ponds Outdoor Center; wander the quaint Main Street, checking out galleries and the town’s historical society.
Yes, Hanover is the home of Dartmouth College. And while the historic buildings around campus are a great draw, there are many other reasons to visit Hanover as well. And if your visit goes well, perhaps you might move here — Hanover has been named one of the best places to live by CNNMoney.
Where to stay: The Hanover Inn, for a room overlooking Dartmouth’s green; Trumbull House Bed & Breakfast, to be a little farther from campus.
Where to eat: Molly’s Restaurant & Bar, for burgers, salads, sandwiches, and more; Murphy’s on the Green, for a slightly more upscale casual experience; Dirt Cowboy Café, for coffee.
What to do: See the works on display at the Hood Museum of Art, on Dartmouth’s campus; browse the literature at Left Bank Books; lounge around Dartmouth’s green and people watch as students and faculty pass by.
Settlers first arrived in what is now Camden in the mid-18th century, and the town has grown since then to a population of just under 5,000 people. While the town was originally a haven for manufacturing, especially the creating of seafaring vessels, it is now most known as a fantastic tourist destination.
Where to stay: The Grand Harbor Inn, for luxury on the waterfront; the Maine Stay Inn, for a cozy getaway.
Where to eat: The Camden Deli, for your favorite deli classics; the Waterfront, for seafood and steak; Cappy’s Chowder House, for chowder, obviously.
What to do: Hike around Camden Hills State Park; go sailing around Camden Harbor; walk around the High Street Historic District to take in the classic New England architecture.
Lying in the highest valley between New York and Montreal, Dorset is the perfect spot for a relaxing weekend. Dorset is known for having some of the oldest marble quarries in the country, providing marble to landmarks like the New York City Library. Though the quarries aren’t used as much anymore, they still make great swimming holes for the locals.
Where to stay: The Dorset Inn, a historic hotel that has been open for over 200 years.
Where to eat: Barrows House Restaurant, a gastropub within the Barrows House Inn; Mio Bistro, for Mediterranean-inspired food.
What to do: Wander the Dorset Farmer’s Market in search of fresh local goods; check out a show at the Dorset Playhouse.
OK, so this is kind of cheating, being a county and not a town. But although Berkshire County consists of numerous small municipalities (the largest, the city of Pittsfield, clocks in at under 50,000 residents), many consider “The Berkshires” to be a cohesive destination in and of itself. The area is known for its natural beauty, with gently rolling hills giving way to mountains for skiing, as well as a strong local arts scene.
Where to stay: The historic Red Lion Inn in Stockbridge.
Where to eat: Baba Louie’s (multiple locations) for pizza; Rouge, in West Stockbridge, for French cuisine; Chocolate Springs Café, in Lenox, for all kinds of desserts.
What to do: View the contemporary art at Mass MoCA in North Adams; watch dancers perform in a natural setting at Jacob’s Pillow in Becket; visit the Norman Rockwell Museum in Stockbridge and stroll around Main Street, which helped inspired some of Rockwell’s work.
You’ve likely heard of Exeter, the home of the famed prep school Philips Exeter Academy. However, this historic town, founded in 1638, has much more to offer than just that.
Where to stay: Inn by the Bandstand, located near the historic bandstand where the Exeter Brass Band plays summer concerts.
Where to eat: The Green Bean, a small New Hampshire chain, for delicious soups; Me and Ollie’s, for sandwiches and salads; Blue Moon Evolution, for local and organic fare.
What to do: Check out the American Independence Museum to see an original printing of the Declaration of Independence as well as original drafts of the Constitution; wander the campus of Philips Exeter Academy to take in both historic architecture and buildings by modern masters like Louis Kahn.
Occupied since the early 1600s, Castine is one of the oldest communities in the United States. The settlement was occupied by the French, and even briefly by the Dutch, during its early history. Today, it is home to just under 1,500 permanent residents.
Where to stay: The Pentagoet Inn, a B&B experience in an old Queen Anne Victorian-style building.
Where to eat: Dennett’s Wharf, for a classic New England seafood experience; Markel’s Bakehouse, for all manners of pastries, cookies, and cakes.
What to do: Get a tour of the State of Maine ship located at the Maine Maritime Academy; explore around the Dice Head Lighthouse; learn about local history at the Wilson Museum.
Located on the northeastern shore of Martha’s Vineyard, the town of Oak Bluffs is one of the island’s main municipalities and a perfect spot from which to explore the rest of the island. The town is known for its unique, brightly colored “gingerbread cottages,” which give the area a fairytale feel.
Where to stay: Isabelle’s Beach House, located right on the waterfront; The Oak Bluffs Inn, located along the town’s main drag.
Where to eat: Nancy’s, which gives options for both a more upscale meal or a classic fried-seafood snack. Lookout Tavern, for seafood including sushi; Back Door Donuts, part of the Martha’s Vineyard Gourmet Café & Bakery, which offers fresh donuts and fritters late nights.
What to do: People watch in Ocean Park, surrounded by gingerbread cottages and across from the town beach; go shopping along Circuit Avenue, the town’s main street; relive your childhood at the Flying Horses Carousel, the oldest platform carousel in the country.
With just over 30,000 people, Falmouth is actually one of the largest towns on this list. It’s comprised of various villages, including Woods Hole, home to numerous marine science institutions that do research in the area. Unlike some of the more popular Cape towns, Falmouth is located on the lower part of the Cape — which gives you a whole different Cape experience.
Where to stay: Wood’s Hole Passage Bed & Breakfast Inn, for easy proximity to both Woods Hole and the center of Falmouth; the Captain’s Manor Inn, located in Falmouth’s historic district.
Where to eat: Añejo Mexican Bistro, for Mexican and a tequila bar; The Quarterdeck Restaurant, for seafood and steak.
What to do: Soak in the sun at Falmouth Heights Beach; see the sea creatures at the Woods Hole Science Aquarium; learn about the ocean’s complexities at the Woods Hole Oceanographic Institution.
First organized in the 17th century, the town of Guilford is replete with reminders of its historic past. With many colonial and Victorian homes still standing, architecture is just one of Guilford’s charms. There are various trails and parks where visitors can take in the sights of the Long Island Sound, along which Guilford is located.
Where to stay: Griswold Cottage, a tiny B&B where you can take cooking classes; the B&B at Bartlett Farm, with a farmhouse built in the late 1780s.
Where to eat: Bufalina, for delicious pizza; the Guilford Bistro, for Italian.
What to do: Scour the market at Bishop’s Orchards; walk around the town green, around which the town of Guilford was first settled; view the oldest stone house in New England at the Henry Whitfield State Museum.
A small town in southern New Hampshire, Hancock is easily accessible from many points in New England. The town considers its heart to be the historic meeting house, built in 1820, which is considered among the best Federal-style churches in the state.
Where to stay: The Hancock Inn, the oldest inn in the state, having been in operation since 1789.
Where to eat: Fiddleheads, for sandwiches, panini, and pizza.
What to do: Check out the old meeting house; drive through the Hancock-Greenfield Bridge, a covered bridge built in 1937; hike the trails at the Harris Center for Conservation Education.
The area that makes up Little Compton was originally occupied by the Sakonnet peoples, giving name to the southernmost area in town, Sakonnet Point, which seems to jut out into the water. The English came in the late 17th century, and a few historic homes from that period remain standing to this day.
Where to stay: The Edith Pearl Bed & Breakfast, a dog-friendly option for those who can’t bear to leave their pooch at home; The Stone House, originally constructed in 1854.
Where to eat: The Barn Restaurant, a renovated barn (naturally) that now serves breakfast; The Commons Lunch, another well-known café in town; Crowther’s Restaurant, which has a bit of a “pub” feel and classic food.
What to do: Have some local wine at Carolyn’s Sakonnet Vineyard; shop at Wilbur’s General Store, a classic general store that’s been around for almost a century and a half; wander along Goosewing Beach and enjoy the view.
Wethersfield prides itself on its historic character, maintaining various historic homes for visitors to tour and learn about the lives of early colonial residents. The Historic District, the largest in the state, includes 50 houses built before the Revolutionary War and 100 built by the time of the Civil War.
Where to stay: The Silas W. Robbins House Bed and Breakfast, for historical charm.
Where to eat: Village Pizza, for an easy and delicious bite; Lucky Lou’s Bar and Grill, a pet-friendly bar/restaurant.
What to do: Learn about the town’s historic homes at the Webb-Deane-Stevens Museum; check out some original furnishings and wallpapers at the Hurlbut-Dunham House Museum; peruse the shops and crafts all along Main Street.
Perhaps infamous for being the site of the Bush family’s summer compound, Kennebunkport is, in fact, much more than a destination for would-be political spies. With just around 3,500 residents, Kennebunkport may be small, but it is comprised of many different areas with different personalities — the Lower Village, which acts as a “downtown” in many ways, Cape Porpoise, a small fishing village, and Goose Rocks Beach, the town’s coastline.
Where to stay: The Nonantum Resort, for a larger resort experience; The Captain Lord Mansion, for a romantic getaway.
Where to eat: Alisson’s Restaurant, for casual seafood in the center of town; David’s KPT, for contemporary cuisine with a waterfront location; Pier 77 Restaurant or The Ramp Bar and Grill, for a more upscale or more casual experience, respectively, in the same building.
What to do: Relax in the sun, or walk along the three-mile stretch of sand, at Goose Rocks Beach; visit St. Ann’s Church, a stone church first built in 1887; learn about the history of trolleys and public transit at the Seashore Trolley Museum.
With just over 20,000 residents, Marblehead is actually one of the larger towns on this list. The town has enjoyed a long history as a fishing port, though now focuses more on yachting and boating in Marblehead Harbor. Due to its role in the Revolutionary War, the town claims the (disputed) title of Birthplace of the American Navy.
Where to stay: The Seagull Inn Bed & Breakfast, located on Marblehead Neck; Harborside House, for its views overlooking the harbor.
Where to eat: The Landing Restaurant, for food right on the water; Maddie’s Sail Loft, to eat surrounded by memorabilia commemorating the town’s fishing history; Jack-Tar, for a tavern experience with a twist.
What to do: Explore Fort Sewall, a historic fort used to defend against the British during revolutionary times; lay out on Devereux Beach, located along the sides of the narrow strip of land connecting the main town to Marblehead Neck; tour the Jeremiah Lee Mansion, built in 1768.
Named for George Washington himself, the town of Washington has been around since 1779. Though once a farming community, and later home to various small mills and factories, Washington is now a residential community with a focus on cultural activities.
Where to stay: The Mayflower Grace, for an experience of pure luxury.
Where to eat: The G.W. Tavern, formerly a colonial home from the 19th century; Washington Pizza House, for…pizza, clearly!; Community Table, for an upscale, locally focused meal.
What to do: Learn about the natives who lived in the Washington Area at The Institute For American Indian Studies; go apple picking at the Averill Farm.
It may be the state capital, but don’t be fooled — Montpelier is a charming, small town at heart. And, as the nation’s smallest state capital, you certainly won’t be overwhelmed by political hustle and bustle during your stay.
Where to stay: The High Hill Inn, set atop the rolling hillside; The Inn at Montepelier, a historic inn near the city center.
Where to eat: The Three Penny Taproom, for a wide craft-beer selection and food to accompany it; Skinny Pancake, for crepes and live music; Positive Pie, a small Vermont chain, for pizza and Italian.
What to do: Take a tour of the State House to try to catch a glimpse of state lawmakers; learn about Vermont’s past at the Vermont History Museum; have a picnic at Hubbard Park.
Having only been incorporated in 1962, Sugar Hill is one of the youngest towns in the state of New Hampshire, and one of the smallest as well, with a population of just over 500 people. The town is conveniently located near many ski centers, making it an ideal base for a winter getaway.
Where to stay: The Sugar Hill Inn, which began as a small farmhouse in the 18th century.
Where to eat: Polly’s Pancake Parlor, for made-from-scratch pancakes and New Hampshire maple syrup; the restaurant at the Sugar Hill Inn, for a prix-fixe splurge.
What to do: Explore the goods at Harman’s Cheese & Country Store and try some of their cheddar; visit the Sugar Hill Historical Museum, which contains a sleigh that once belonged to actress Betty Davis.
Situated at the far tip of Cape Cod, Provincetown is as far out as you can travel before there’s nowhere else to go. Provincetown is famed for being one of the most LGBT-friendly towns in the country, but it is much more than just that. Provincetown is a haven for the arts, especially, from theater to painting.
Where to stay: Boatslip Resort, a destination for LGBT travelers and home to the famous Tea Dance in summer; Carpe Diem Guesthouse, an adults-only spa resort for those looking for a grown-up vacation.
Where to eat: The Lobster Pot Restaurant, for seafood on the water; Joe Coffee and Café, for coffee and small bites; Ceraldi, if you’re willing to break the bank on a special meal.
What to do: Enjoy the sun at Race Point Beach; learn about the history of the Pilgrims and the town of Provincetown at the Pilgrim Monument & Provincetown Museum; walk up and down Commercial Street, checking out the shops and galleries along the way.
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