9 Best Weekend Getaways in New England to Visit in 2021

by Global Viewpoint
Best Weekend Getaways in New England

These best weekend getaways in New England will give you a taste of the northeast

The Northeast has so much going for it. Beautiful scenery, compelling history, and New England charm, all within convenient distance of cities like Boston and Cambridge, make this region one of the best places for weekend getaways. Whether you’re into seafood and sports, mountains and lighthouses, or long drives and boat rides, you’ll find plenty of that in the northeast US.

As a native Bostonian, I’ve visited all corners of New England on road trips. Here are the 9 best weekend getaways in New England that you should visit in 2021.

Best weekend getaways in New England pinterest image
Disclosure: I’m the launch partner for a travel app called Curated Planet. In the CP app, I’ve curated itineraries for each of the destinations in this article. Click here to check out the app, or select the Curated Planet buttons embedded below to see my bookable itineraries of the best weekend getaways in New England.

1. Newport, Rhode Island

Looking for a romantic getaway by the ocean? Spend a weekend in Newport.

Newport is a coastal city in Rhode Island within a 2-hour drive of Boston. It’s best known for its Gilded Age mansions, which are decked out with extravagant designs and antiques, bringing a fin de siècle feel to Newport. Many of these mansions are perched atop rugged cliffs, with sweeping views of the coastline and ocean below.

I’ve always been fascinated by Newport, and the wealthy industrial tycoons (the top .01%) who lived there. It’s a place where you could easily spend 2-3 days each season and never get bored of its timeless intrigue. Here are some of the highlights.

Interior of The Breakers, the most famous and luxurious of the Newport Mansions.
Inside The Breakers, the most famous and luxurious of the Newport Mansions.

Top things to see and do in Newport, one of the top weekend getaways in New England

From scenic coastline to mansions-turned-museums, here’s what to see and do in Newport, Rhode Island.

Curated Planet travel app, Newport itinerary

The Breakers

Built in 1893, The Breakers is the most iconic of all the Newport mansions. It was built in 1893 as a summer home for the Vanderbilt family, one of America’s wealthiest and most powerful families. Today, The Breakers is a museum that’s run by the Newport Preservation Society.

The Breakers in Newport, Rhode Island, one of the best weekend getaways in New England
The Breakers
This 70-room, Italian Renaissance-style mansion has stunning views of the Atlantic Ocean. This area is a best place to spend a weekend getaway in New England.
This 70-room, Italian Renaissance-style mansion has stunning views of the Atlantic Ocean.

Marble House

Marble House is another iconic mansion built by the Vanderbilt family. It lies on Bellevue Avenue, a historic residential area that’s home to several other Gilded Age mansions. Built from 500,000 cubic feet of marble, this summer home was a birthday present for William K. Vanderbilt’s wife.

If you only have time to see a couple of mansions, definitely check out Marble House and The Breakers.

The pillars and portico somewhat make this mansion somewhat resemble the White House.
The pillars and portico make this mansion somewhat resemble the White House.

Cliff Walk

Another top sight in Newport is the Cliff Walk, a 3.5-mile walkway that connects many of the Newport mansions with the scenic waterfront area. It’s a great place for a seaside stroll and a beautiful sunrise spot.

Rosecliff

This ornate mansion, now a museum, is another beautiful photo-op. The Rosecliff was filmed in the 1974 film, The Great Gatsby, and gives us yet another taste of how the ultra-rich used to live.

Rosecliff is a must-see mansion in Newport, one of the best weekend getaways in New England.
Rosecliff is a must-see mansion in Newport, one of the best weekend getaways in New England.

Ocean Drive Historic District

Ocean Drive is a scenic drive along the ocean. It runs about 10 miles down the southern coast, where you’ll come across private beaches, classic New England boats, and mansions towering over dramatic cliffs.

Ocean Drive is filled with stunning views like this.
Ocean Drive is filled with stunning views like this.

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Brenton Point State Park

As you continue driving along Ocean Drive, you’ll eventually reach Brenton Point State Park. This 89-acre park is a great place for a picnic and afternoon stroll with stunning views of the Atlantic Ocean and Narragansett Bay.

International Tennis Hall of Fame

If you’re into tennis, you’ll want to make stop by the International Tennis Hall of Fame. It’s very close to several mansions on Bellevue Avenue, including Kingscote and The Elms.

Block Island

If you have time, make a day trip to Block Island, one of the best hidden vacation spots in the US. It’s just a short ferry ride from Newport. You won’t regret it!

How to get to Newport, Rhode Island

Driving is the best way to get here. If you’re not from the northeast, then consider flying into Boston, New York City, or Providence, and then renting a car. You can also take the Amtrak train or a bus from one of these cities.

In addition to being a great weekend destination, Newport is close enough to Boston to be the perfect day trip.

Where to stay in Newport, one of the best New England weekend getaways

Here’s where I recommend staying in Newport, Rhode Island.

$: Newport Inn, The Outlook Inn,
$$: Newport Marriott
$$$: The Chanler at Cliff Walk

Where to eat in Newport, Rhode Island

Here are some of my favorite cafés and restaurants in Newport, Rhode Island.

Breakfast: Corner Café, Rosemary & Thyme Café
Lunch: 22 Bowen’s Wine Bar & Grille, Pour Judgment
Dinner: The Mooring Seafood Kitchen & Bar, White Horse Tavern
Dessert: Kilwins Chocolates & Ice Cream

Fun facts about Newport, Rhode Island

  • The Breakers, home of the affluent Vanderbilt family, was built in 1895 at a cost of $150 million (in 2021 dollars).
  • Built in 1673, The White Horse Tavern in Newport is the country’s oldest tavern in continuous use.
Curated Planet travel app, Newport RI itinerary
The Breakers is the most iconic building in Newport. It's a wonderful way to spend a weekend getaway in New England.
The Breakers is the most iconic building in Newport, Rhode Island.

2. The Berkshires, Massachusetts

Craving a nature getaway on the east coast? You won’t want to miss the Berkshires.

Just a 3-hour drive from Boston and NYC, the Berkshires is a weekend retreat brimming with nature and character. This region in Western Massachusetts extends from the tip of the Vermont border to the Connecticut state line. It’s home to charming B&Bs, intriguing museums, exhilarating outdoor activities, and exquisite farm-to-table dining. These cool things, along with the immaculate nature, make it a top romantic escape in New England.

In this neck of the woods, outdoorsy types will find plenty of hiking trails and farmlands offering a taste of the countryside. Similarly, city people fall in love with the Berkshires for its eclectic country culture, best showcased by art museums and music festivals.

The Berkshires deserves a top spot among the best weekend getaways in New England.
The Berkshires deserves a top spot among the best weekend getaways in New England.

Top things to see and do in the Berkshires, a top weekend getaway in New England for nature lovers

From the gorges to the galleries, here’s what you should do when you visit the Berkshires.

Curated Planet travel app, Berkshires itinerary, which is top among the best weekend getaways in New England.

Canoe or Kayak Tour

One of my favorite activities in the Berkshires is canoeing down the Housatonic River on a guided tour with Berkshire Canoe Tours. This river is quiet and serene, allowing you to soak in the beautiful nature and learn about the wildlife that lives here.

Nothing beats kayaking in the middle of nature.
Nothing beats kayaking in the middle of nature.

Whitewater rafting

The more adventurous types may opt to go whitewater rafting in the Berkshires. Deerfield River, which lies on the northeastern tip of the region, is a great spot for this.

Norman Rockwell Museum

Art lovers will definitely want to check out the Norman Rockwell Museum. It’s fascinating to learn about Norman Rockwell’s magnificent artwork and legacy on American history. From “The Four Freedoms” to “Home for Christmas”, Norman Rockwell’s collection is an artistic inspiration.

Norman Rockwell Museum in Stockbridge, MA.
Norman Rockwell Museum in Stockbridge, MA.

Hancock Shaker Village

My favorite museum in the Berkshires is the Hancock Shaker Village in Pittsfield. Established in the late-1700s, Hancock Shaker Village is a historic landmark that offers a glimpse of the simple and rustic lifestyles of the Shakers. Like the Quakers, the Shakers were a Christian sect that passionately practiced pacifism, equality, and sustainability.

The round stone barn at Hancock Shaker Village. This town in the Berkshires is one of the best weekend getaways in New England.
The round stone barn at Hancock Shaker Village.

Downtown Stockbridge and Great Barrington

These two towns are charming, quirky, and certainly worth a quick pit stop. Each of them has a Main Street that combines country vibes with a more modern, hipster feeling.

Great Barrington is home to SoCo, one of my favorite ice cream joints.
Great Barrington is home to SoCo, one of my favorite ice cream joints.

Mount Greylock State Reservation

Mount Greylock is the tallest mountain in Massachusetts, home to 33 hiking trails and plenty of scenic overlook points. You can drive right up to the top, where you’ll have beautiful views of the surrounding landscape.

Mass MoCa Museum

This factory-turned-art-museum in North Adams is one of the largest contemporary art galleries in the US. Much of the art on display is edgy and eccentric, creating a thought-provoking and unconventional museum experience.

Mass MoCA Museum in the Berkshires is one of the best weekend getaways in New England.
Mass MoCA Museum.

How to get to the Berkshires

The best way to get here is by car. If you’re not from the northeast, you can rent a car from one of the nearby major cities (i.e. Boston and New York City). Though there are also buses to get here, you’ll need a car to reach all the best spots.

Where to stay in the Berkshires, a unique New England getaway

Here’s where I recommend staying in the Berkshires.

$: Chambery Inn, Red Lion Inn
$$: Harbour House Inn B&B
$$$: Garden Gables Inn

Where to eat in the Berkshires

Here are some of my favorite cafés and restaurants in the Berkshires.

Breakfast: Haven Café & Bakery, Marketplace Kitchen Table
Lunch: No. Six Depot Roastery and Café, Red Lion Restaurant
Dinner: Trail House Kitchen & Bar, Chez Nous Bistro
Dessert: Chocolate Springs Café
Trail House Kitchen in North Adams has mastered the art of farm-to-table dining.
Trail House Kitchen in North Adams has mastered the art of farm-to-table dining.

Fun facts about the Berkshires

  • From the top of Mount Greylock (3,489 feet), you can see 5 states on a clear day.
  • The Berkshires has mastered the art of farm-to-table dining. From Great Barrington to North Adams, you’ll find that most restaurants serve fresh and locally-sourced ingredients.
Curated Planet travel app, Berkshires MA itinerary
The Berkshires in Western Massachusetts.
The Berkshires in Western Massachusetts.

3. Ogunquit, Maine: Among the best weekend getaways in New England

Just over an hour north of Boston, Ogunquit is the quintessential New England town. It gently hugs the sea, and offers a variety of fun outdoor activities.

I’ve been coming here every year for as long as I can remember. Ogunquit has always been one of my favorite New England weekend getaways.

This town is also home to quaint inns, shops, and seafood restaurants that embody New England’s coastal charm.

Ogunquit is definitely one of the top weekend getaways in New England.
Ogunquit is definitely one of the top weekend getaways in New England.

Top things to see and do in Ogunquit

From soaking in the gentle sea breeze to perusing local artisan shops, here’s what to do in Ogunquit, Maine.

Curated Planet travel app, Ogunquit itinerary

Ogunquit Beach

This 3.5-mile beach is a popular place for families to spend a warm summer’s day. Though the water is pretty cold (it is Maine, after all), you can also play beach sports, build sandcastles, or simply sunbathe. There are also some restaurants and gift shops nearby.

The Marginal Way

This is my favorite part of Ogunquit. The Marginal Way is a scenic, coastal trail that brings you from the center of Ogunquit to Perkins Cove, another scenic sight you’ll want to visit. Nothing beats hearing the sound of waves crash against this rugged coastline.

Perkins Cove

This tiny cove is home to many fishing and lobster boats, as well as boutiques and classic New England restaurants. There’s also a hand-operated footbridge where you can look out into the harbor and capture that perfect Instagram photo. The freshest seafood in town is sold in this area.

Perkins Cove in Ogunquit.
Perkins Cove in Ogunquit.

Lighthouse cruise or lobstering trip

Many scenic boat trips leave from Perkins Cove, including lobster, fishing, and lighthouse cruises. Finestkind Cruises not only shows you the most beautiful sights in the area, but it also provides interesting commentary that makes for an enriching experience.

Nubble Lighthouse

Cape Neddick Light, also known as the Nubble Lighthouse, is just a town over from Ogunquit. This iconic lighthouse was built in 1879 to provide light and clarity to those making the treacherous voyage through the sea. Today, it’s a classic American lighthouse that you can’t miss it during your visit to Ogunquit!

Nubble Lighthouse in all of its glory.
Nubble Lighthouse in all of its glory.

How to get to Ogunquit

The best way to get here is by car (or by boat – if you can swing it!). Once you get into town, you won’t need to drive anywhere else, unless you plan to visit the surrounding towns like Wells, York, or Kennebunkport. Because it’s so close to Boston, Ogunquit is definitely one of the best last minute weekend getaways in New England.

Where to stay in Ogunquit for a unique New England getaway

Here’s where I recommend staying in Ogunquit.

$: The Admiral’s Inn
$$: Gorges Grant Hotel, Beachmere Inn, Meadowmere Resort
$$$: Cliff House Maine

Where to eat in Ogunquit

Here are some of my favorite cafés and restaurants in Ogunquit, Maine.

Breakfast: Backyard Coffeehouse & Eatery, Cove Café
Lunch: Barnacle Billy’s, Lobster Shack
Dinner: The Front Porch Piano Bar & Restaurant, Five-O Shore Road
Dessert: Rococo Ice Cream
Barnacle Billy's is my favorite lunch and ice cream spot in town.
Barnacle Billy’s is my favorite lunch and ice cream spot in town.

Fun fact about Ogunquit

  • The name “Ogunquit” comes from the Algonquian (Native American) language, meaning “beautiful place by the sea.”
Curated Planet travel app, Ogunquit ME itinerary
The Marginal Way in Ogunquit is an amazing place to catch the sunset. It's also one of the best weekend getaways in New England.
The Marginal Way is an amazing place to catch the sunset.

4. Burlington, Vermont

Burlington is an earthy-crunchy city nestled on the shores of Lake Champlain. It’s best known for its shopping, boating, culinary scene, and craft beer.

Overlooking Lake Champlain, Burlington is an idyllic outdoor haven that embraces nature and the arts. As the first U.S. city to run completely on renewable energy, Burlington has a reputation for being a forward-thinking city. As such, you should really think ahead and consider Burlington as your next weekend getaway.

Top things to see and do in Burlington, one of the coolest weekend getaways in the northeast

From strolling and shopping to enjoying a beer or two (or three…), here’s what to do in Burlington, Vermont.

Curated Planet travel app, Burlington itinerary
Burlington lies right on Lake Champlain.
Burlington lies right on Lake Champlain.

Church Street Marketplace

Home to many shops, restaurants, and bars, Church Street is one of America’s most lively public spaces. This quaint pedestrian zone was inspired by the Strøget (Copenhagen’s most popular shopping street). When venturing down Burlington’s acclaimed Church Street, be sure to make some room for Champlain Chocolates and a craft beer.

Church Street in Burlington is one of the best ways to spend a weekend getaway in New England.
Church Street in Burlington, VT.

Burlington Farmers Market

Every Saturday, Burlington’s finest farmers congregate in town for the Burlington Farmers Market. Here, you’ll have a taste of some of Vermont’s freshest and most delicious produce, meats, and treats. It’s a great way to support the local community while trying some incredibly delicious food.

Pub crawl and/or brewery tour

If you haven’t gotten the gist already, Burlington is known for its craft beer scene. There are many fantastic microbreweries in town that you’ll want to try, including Foam Brewers, Zero Gravity, and Switchback Brewing Company. When you’re at dinner, always ask for a local’s recommendation on the best beers to try (though it may be a difficult answer, because there are so many of them!).

The hoppiest beer I've ever had is in Burlington, Vermont.
The hoppiest beer I’ve ever had is in Burlington.

Burlington Bike Path

Renting bikes or segways is a great way to get around Burlington. There’s a nice path that connects Waterfront Park and Battery Park to Appletree Point, offering scenic views of the lake and the parks that skirt around it. Most of the path is flat, well-maintained, and perfect for a bike ride.

Bikes are a great way to experience Burlington, one of the best weekend getaways in New England.
Bikes are a great way to experience Burlington, one of the best weekend getaways in New England.

Boat cruise on Lake Champlain

With a surface area of 500 square miles, Lake Champlain is a massive lake that touches Burlington, Vermont. During the summer, it’s a great place for watersports, fishing, and boat cruises.

Whistling Man Schooner Company offers daytime and sunset cruises that give you a glimpse of the local landscape. The Spirit of Ethan Allen is another scenic and narrated cruise that departs from Burlington. There are many great options to choose from, all giving you a unique perspective of the city and its surroundings.

How to get to Burlington, Vermont

Depending on where you’re coming from, there are many convenient ways to get to Burlington, Vermont. Driving is the most economical option, where you can either drive up on your own or rent a car from cities like Boston, Albany, or Montreal. You can also fly directly into the nearby Burlington International Airport.

If you’re coming to Burlington from another part of the lake, you can hop aboard Lake Champlain Ferries to get here as well.

Where to stay in Burlington, Vermont

Here’s where I recommend staying in Burlington, Vermont.

$: Best Western Burlington
$$: Hilton Burlington
$$$: Hotel Vermont, Courtyard by Marriott

Where to eat in Burlington, Vermont

Here are some of my favorite cafés and restaurants in Burlington, Vermont.

Breakfast: Penny Cluse Café, Mirabelles Café
Lunch: August First, Henry’s Diner
Dinner: Bistro de Margot, Hen of the Wood
Dessert: Ben & Jerry’s
Ben & Jerry's is a highlight of any trip to Vermont.
Ben & Jerry’s is a highlight of any trip to Vermont.

Fun fact about Burlington, Vermont

  • The first Ben & Jerry’s store opened in Burlington in 1978.
Curated Planet travel app, Burlington VT itinerary
In December, Church Street is decked out for the Holidays.
In December, Church Street is decked out for the Holidays.

5. Martha’s Vineyard, Massachusetts is a top New England weekend getaway

Martha’s Vineyard is an island just off the coast of Cape Cod. It’s the ideal New England weekend getaway, especially during the summer, when you can take advantage of its charming towns, lighthouses, beaches, and farms. It’s right up there with Nantucket as a top romantic weekend getaway in New England.

Martha’s Vineyard has an almost exclusive feel to it, as there are no chain restaurants or hotels to be found. Its beautiful nature and “back country” vibes likely haven’t changed in over a century, which is precisely the draw for many New Englanders and urbanites who come here.

Aquinnah Cliffs in Martha's Vineyard.
Aquinnah Cliffs in Martha’s Vineyard.

Top things to see and do in Martha’s Vineyard

From riding mopeds on open roads to staring down life-sized gingerbread houses, here’s what to do in Martha’s Vineyard.

Curated Planet travel app, Martha's Vineyard MA itinerary

Rent mopeds or bikes

Mopeds are a fun and convenient way to get around Martha’s Vineyard. This way, you’ll have full flexibility to explore all the nooks and crannies around the island.

Martha’s Vineyard is one of the most moped-friendly places I’ve ever visited, as there’s usually very little traffic on the roads. If you’re afraid of mopeds or don’t want to assume the cost, I recommend renting bikes instead.

Renting mopeds is the best way to get around in Martha's Vineyard.
Renting mopeds is the best way to get around in Martha’s Vineyard.

Gingerbread cottages

Martha’s Vineyard is known for its vibrant gingerbread cottages. These quaint, 19th-century homes are found in Oak Bluffs, the second largest town on the island after Edgartown.

The Gingerbread Cottages are a great place for a stroll and taking the perfect Instagram photo.
The Gingerbread Cottages are a great place for a stroll and taking the perfect Instagram photo.

Read next: 11 Unique Vacation Rentals in Massachusetts

Beautiful beaches

Like the rest of Cape Cod, Martha’s Vineyard has its fair share of beautiful beaches that are ideal for swimming and other outdoor activities.

Joseph Sylvia State Beach and Katama Beach are popular beaches in Oak Bluffs and Edgartown, respectively.

Aquinnah Public Beach is one of the best beaches on the western part of the island. It’s nestled alongside Gay Head Lighthouse, a brick beacon built in the late 1700s.

Aquinnah in Martha's Vineyard is among the best weekend getaways in New England.
Aquinnah in Martha’s Vineyard.

Explore Oak Bluffs and Edgartown

Oak Bluffs and Edgartown are two charming towns where you’ll find most of the accommodations on Martha’s Vineyard. (Be sure to find a vacation rental along the waterfront!)

Oak Bluffs is best known for its gingerbread cottages and other Victorian-era buildings. It’s also home to the Flying Horses Carousel, the oldest carousel in America, and an alpaca farm called Island Alpaca Company.

Edgartown was the first colonial settlement on Martha’s Vineyard. It has a 500-acre wildlife refuge, as well as beautiful beaches and lighthouses. Edgartown is also connected by ferry to Chappaquiddick Island, another must-see place in Martha’s Vineyard.

Read next: Coolest Airbnbs in Cape Cod

Cape Poge Lighthouse on Chappaquiddick Island.
Cape Poge Lighthouse.

How to get to Martha’s Vineyard

Martha’s Vineyard is accessible by ferry or plane. The ferry ride is 45 minutes from Woods Hole, and the flight from Boston via Cape Air is also just under an hour. 

Many visitors to Martha’s Vineyard bring their cars to the island via ferry. For those who take flights or passenger ferries to get here, the best option to get around the island is by moped or public buses (Vineyard Transit Authority). Taxis and rental cars are an alternative, but in my opinion, they’re pricey and not worth it.

Where to stay in Martha’s Vineyard, an exclusive weekend getaway in New England

Here’s where I recommend staying in Martha’s Vineyard.

$: HI Martha’s Vineyard Hostel
$$: Clark House
$$$: Mansion House, Lambert Cove Inn

Where to eat in Martha’s Vineyard

Here are some of my favorite cafés and restaurants in Martha’s Vineyard.

Breakfast: Art Cliff Diner, Little House Café
Lunch: The Newes American Pub, Lucky Hank’s
Dinner: L’Etoile Restaurant, The Red Cat Kitchen
Dessert: Murdick’s Fudge, Mad Martha’s

Fun fact about Martha’s Vineyard

  • Martha’s Vineyard is a popular summer destination for the rich and famous. Several former U.S. presidents, including Barack Obama and Bill Clinton, have been spotted here.
Curated Planet travel app, Martha's Vineyard itinerary
Martha's Vineyard is a serene place to spend a weekend getaway in New England.
Martha’s Vineyard is a serene place to spend a weekend getaway in New England.

6. White Mountains, New Hampshire

The White Mountains region of New Hampshire is a top-notch New England getaway during all seasons. In the summer, people flock here for the hiking, camping, and canoeing. In the winter, it transforms into a world-class ski destination, with snow-capped mountains extending as far as the eye can see.

This region is vast, so it’s best to organize your itinerary based around the different sub-regions, which include Mount Washington Valley, Bretton Woods, Franconia Range, and the Kancamagus Highway

Looking to discover one of the best weekend getaways in New England? Let’s take a trek through the White Mountains, a region brimming with unspoiled nature, outdoor activities, and shopping.

The White Mountains are among the best weekend getaways in New England.
In the summer, much of the White Mountains are no longer white. Don’t worry, they’ll be snow-capped again in the winter.

Top things to see and do in the White Mountains

From long drives in the wilderness to epic snow-capped peaks, here’s what to do in the White Mountains, an amazing summer and winter getaway in New England.

Kancamagus Highway

This 35-mile highway is up there on my list of the most scenic drives in New England. You’ll pass stunning forest scenery, creeks and gorges, and cascading waterfalls. As you can imagine, this area is especially beautiful during the fall foliage months. If you’re looking for an epic hiking trail in New England, you’ll definitely want to check this out.

Breathtaking scenery is abundant along the Kancamagus Highway, one of the best weekend getaways in New England.
Breathtaking scenery is abundant along the Kancamagus Highway.

Mount Washington Cog Railway

In operation since 1868, the Mount Washington Cog Railway is definitely the most exciting way to experience the White Mountains. This three-hour roundtrip ride takes you to the top of Mount Washington (6,288 feet), the tallest mountain in the northeast.

The Cog Railway brings you up the mountain, where you'll have sweeping views of the landscape.
The Cog Railway brings you up the mountain, where you’ll have sweeping views of New Hampshire’s landscape.

Omni Mount Washington Resort

Built in 1902, the Omni Mount Washington Resort is a historic landmark that shows the region’s luxurious side. This grand hotel is one of the most iconic buildings in New England, and certainly a place to spend your weekend getaway. Even if you’re not already staying here, you’ll want to stop by briefly to check it out.

The Omni Mount Washington Resort is a great place to stop by for lunch, a drink, and to admire its splendid property.
The Omni Mount Washington Resort is a great place to stop by for lunch, a drink, and to admire its splendid property.

Clark’s Trading Post

If you’re looking to spend a few hours doing something a little different, head over to Clark’s Trading Post. This family-run trading post is kind of like a mini-theme park, home to everything from bumper boats and segway rides, to gift shops and a black bear show.

North Conway

If you’re into shopping, shop ‘til you drop in North Conway. This town is known for its antique shops and brand-name outlets, giving visitors a taste of the old world and the new. It’s also home to many scenic spots for hiking, biking, and of course, skiing.

If you have time after all the shopping, head over to the Conway Scenic Railroad. Then, hop aboard a vintage 19th-century train and explore the mountains and streams around town.

Cannon Mountain

Cannon Mountain is a 4,000 ft. (1,240 m) peak in the northwestern side of the White Mountains region. In the winter, it’s a popular skiing area; in the summer and fall, it’s got a tramway that brings you to the top. As such, it’s a top winter getaway in New England.

On a clear day, you can see Canada and four U.S. states (New Hampshire, Vermont, Maine, and Massachusetts) from the top.

Other scenic sights in the area include The Flume, Franconia Notch, Echo Lake Beach, and Artist Bluff Trail. If you have time, you should stop by these places to experience the unspoiled nature of New Hampshire.

Other scenic spots

There are lots of other hiking spots you’ll want to check out. If you’re in the Kancamagus Highway area, you’ll want to stop by the following spots:

– Boulder Loop Trailhead

– Rocky Gorge Scenic Area

– Champney Falls Trailhead

– Sabbaday Falls

Waterfalls and flumes galore in the White Mountains.
Waterfalls and flumes galore in the White Mountains.

How to get to the White Mountains, one of the coolest weekend getaways in New England for outdoor junkies

Driving is the best way to get here and explore this vacation destination. If you’re not from New England, I recommend renting a car from either Boston or Manchester, New Hampshire.

Where to stay in the White Mountains

Here’s where I recommend staying in the White Mountains region of New Hampshire.

$: The Inn at Thorn Hill & Spa
$$: North Conway Grand Hotel, Omni Bretton Arms Inn at Mount Washington
$$$: Omni Mount Washington Resort, RiverWalk Resort at Loon Mountain
The Omni Mount Washington Resort is one of the best places in New England to spend a weekend getaway.
The Omni Mount Washington Resort in all its glory.

Where to eat in the White Mountains

Here are some of my favorite cafés and restaurants in the White Mountains region of New Hampshire.

Breakfast: Leavitt’s Country Bakery, The Sunshine Shack
Lunch: Black Mtn. Burger Co., Mary Kelly’s Cottage
Dinner: Mary Kelly’s Cottage, White Mountain Cider Co.
Dessert: Trails End Ice Cream Shop

Fun fact about the White Mountains

  • Mount Washington (6,288 feet) is known for having the world’s most extreme weather conditions. The highest wind gust ever recorded in the world occurred here in 1934 (231 mph).
The White Mountains are especially beautiful during the fall foliage season.
The White Mountains are especially beautiful during the fall foliage season in New England.

7. Portland, Maine

Portland is New England at its best. On one hand, this city has an old seaport vibe that’s so quintessentially Maine. On the other hand, it has an eclectic mix of museums and art galleries, parks and greenspaces, and some of the region’s best microbreweries and restaurants. The port city of Portland is a fantastic place to spend a weekend getaway in New England.

Though the largest city in Maine, Portland has preserved its fishing village vibe.
Though the largest city in Maine, Portland has preserved its fishing village vibe.

Top things to see and do in Portland

From a historic port with salty air to hipster breweries and cafés, here’s what to do in Portland, Maine.

Old Port

This is the historic center of town where you’ll find the best restaurants, bars, and boutiques. It’s characterized by its quaint cobblestone streets and brick buildings. If you’re looking for some traditional, Maine-style seafood, the Old Port is the place to go.

After exploring the Old Port, you can easily walk to other top sights like the Portland Museum of Art and Victoria Mansion. You can also hop on a ferry to explore the islands of Casco Bay.

The Old Port during the winter is one of the best weekend getaways in New England.
The Old Port during the wintertime.

Portland Head Lighthouse

Portland Head Lighthouse is another historic landmark that is so Maine. It’s perched on a rocky ledge 100 feet above the water, watching over the rough seas below. First lit in 1791, it’s the oldest lighthouse in Maine and definitely among the most iconic. Portland Head lies in Fort Williams Park on the outskirts of town, a 15-minute drive from the center of Portland.

Portland Head is among the most iconic lighthouses and best weekend getaways in New England.
Portland Head is among the most iconic lighthouses in New England.

Portland’s Brewery Scene

Portland has a few excellent breweries that are, in my opinion, among the best in New England.

Allagash Brewing Company is one of the most well-known breweries in the northeast US. They specialize in Belgian-style beer, some of which remind me of the Duvel and Delirium beers I enjoyed in Brussels. For $5 you can go on a stellar beer tour, where you’ll learn about the brewery and taste some of its world-class beer.

Bissel Brothers, Shipyard, and Rising Tide Brewing Company are a few other top-notch breweries in Portland that you’ll want to check out.

I love Allagash beer so much that I even had some as I was writing this article.
I love Allagash beer so much that I even had some as I was writing this article.

Take a cruise in Casco Bay

From the port, you can hop aboard a ferry to do some sightseeing around Casco Bay. Using ferry services like Casco Bay Lines, you can visit some of the surrounding islands such as Peaks Island and Cliff Island. The Harbor Light and Sights Cruise is one of the favorites, but you can also hitch a ferry to get to and from the many islands in the bay.

How to get to Portland, Maine

The best way to get to Portland is by car. That way, you can stop by other cute towns on the way through Maine, New Hampshire, and Massachusetts. You can also take a bus or Amtrak train, or even fly into Portland’s very own international airport.

Where to stay in Portland, Maine

Here’s where I recommend staying in Portland, Maine.

$: Inn at St John
$$: The Westin Portland Harborview, Portland Harbor Hotel
$$$: Hyatt Place Portland-Old Port

Where to eat in Portland, Maine

Here are some of my favorite cafés and restaurants in Portland, Maine.

Breakfast: Bam Bam Bakery, Bayside American Café
Lunch: Flatbread Company, Old Port Sea Grill & Raw Bar
Dinner: Lolita, Back Bay Grill
Dessert: Dean’s Sweets

Fun fact about Portland, Maine

  • Portland is Maine’s largest city. Approximately 40% of the state’s residents live in the greater Portland area.
Portland is much more industrial than one would expect for a place in Maine. It's definitely one of the best weekend getaways in New England.
Portland is much more industrial than one would expect for a place in Maine.

8. Stowe, Vermont

Looking for a weekend trip only a few hours from Boston? Stowe is another year-round destination that embodies the best New England has to offer. It’s a popular place for hiking, camping, and biking during the summer and skiing in the winter. The mountains and alpine-style lodging make you feel like you’re in Austria. At the same, Stowe’s farm-to-table dining and variety of outdoor activities are so Vermont.

With so many mountains, hiking trails, and lodges to choose from, it’s no wonder Stowe is one of the best weekend getaways in New England.

Top things to see and do in Stowe, one of the best New England getaways for foodies

Mount Mansfield

At over 4,395 feet (1,339 m) elevation, Mount Mansfield is the highest mountain in Vermont. During the summer and fall months, it’s a great place for hiking, zip lining, and mountain climbing. You can take a scenic drive up to the top, along the 45-mile Stowe Mountain Auto Toll Road, giving you a glimpse of the Adirondacks and Lake Champlain in the distance. Afterwards, consider a brewery tour or tasting at the Alchemist or 4 Points VT Brewery.

Flying my drone near Mount Mansfield.
Flying my drone near Mount Mansfield.

Alchemist Brewery

This small, family-run brewery is a highlight of any visit to Stowe, Vermont. I’ve been obsessed with this brewery since I was an intern in college, working for a client in Vermont. The Alchemist is well-known for its flagship double IPA, the Heady Topper. After drinking a beer or a few, walk it off on Main Street, where you can check out the Giles W. Dewey Bridge and local arts and crafts shops.

I was very enthusiastic with my Instagram stories here last summer. Burlington is one of the best weekend getaways in New England.
I was very enthusiastic with my Instagram stories here last summer.

Stowe Recreation Path

The Stowe Recreation Path is a 5-mile path that’s perfect for bike riding and hiking. The path goes through Cady Hill Forest, where you’ll catch a glimpse of more than 250 acres of beautiful landscapes and scenic vistas. With such stunning views and low prices throughout Stowe, it’s among the most affordable and romantic weekend getaways in New England.

Smugglers Notch State Park

Located near Mount Mansfield, Smugglers Notch State Park is another beautiful sightseeing spot in the Green Mountains. There are many popular hiking trails here that pass thickly settled forests and raging waterfalls. If you have time, be sure to check out Bingham Falls, Spruce Peak, and Sterling Gorge Falls which are situated nearby.

How to get to Stowe, Vermont

The most reliable way to get here is by car. If you’re not from the northeast, your best bet is to pick up a car rental from Burlington, Boston, Albany, or Montreal. You can also take a bus or Amtrak Train to Waterbury, a small town that lies nearby.

Where to stay in Stowe, one of the best weekend getaways in New England

Here’s where I recommend staying in Stowe, Vermont.

$: Innsbruck Inn, Northern Lights Lodge
$$: Trapp Family Lodge
$$$: The Lodge at Spruce Peak
Innsbruck Inn in Stowe, Vermont is among the best weekend getaways in New England.
Innsbruck Inn in Stowe, Vermont.

Where to eat in Stowe, Vermont

Here are some of my favorite cafés and restaurants in Stowe, Vermont.

Breakfast: Trapp Kaffeehaus, Butler’s Pantry
Lunch: Doc Ponds, Von Trapp Brewery & Bierhall, Piecasso
Dinner: Von Trapp Brewery & Bierhall, Harrison’s Restaurant, The Bistro at Ten Acres
Dessert: Laughing Moon Chocolates
Von Trapp Brewery & Bierhall. This is one of the best weekend getaways in New England.
Von Trapp Brewery & Bierhall

Fun facts about Stowe, Vermont

  • Stowe is home to Mt. Mansfield (4,395 ft), the tallest mountain in Vermont.
  • Are you a huge fan of “The Sound of Music” like I am? The Von Trapp family settled in Stowe, Vermont. The Trapp Family Lodge is fully owned and operated by the family to this day.
Filled with scenery at every turn, Stowe is certainly one of the best weekend getaways in New England.
Filled with beautiful scenery at every turn, Stowe is certainly one of the best weekend getaways in New England.
Curated Planet travel app, Stowe Vermont itinerary

9. Acadia National Park, Maine

Home to some of the most pristine nature that New England has to offer, Acadia National Park definitely merits a weekend getaway (or much longer!).

Jordan Pond is a must-see in Acadia National Park, one of the coolest weekend getaways from Boston.
Jordan Pond is a must-see in Acadia National Park, one of the coolest weekend getaways from Boston.

Located on Mount Desert Island, this is one of the few national parks on the East Coast, and definitely a place you’ll want to add to your travel bucket list.

Because Acadia is about 5 hours from Boston, you’ll want to spend at least 4-5 days here. This will give you enough time to cover the highlights, which include sights like Cadillac Mountain, Jordan Pond, Thunder Hole, Park Loop Road, and more. I felt it was important to mention Acadia among the top weekend getaways in New England, but you’ll definitely want to spend more time than just a couple of days. You won’t run out of beautiful hiking trails, and there are plenty of viewpoints overlooking mountains, lakes, and the coastline. Acadia truly has it all!

Cadillac Mountain is a top sunrise and sunset spot in Acadia National Park.
Cadillac Mountain is a top sunrise and sunset spot in Acadia National Park.

Top weekend getaways in New England to visit in 2021

I hope you enjoyed my round-up of the best weekend getaways in New England. As someone who grew up just outside of Boston, I’ve been each of these places several times and can’t get enough of them!

Which destinations do you think are the best weekend getaways in New England? I’d love to hear them, and tack on a few other places to this list in the future!

Happy Travels!

Jon

Looking to go on a road trip around New England? Check out my Ultimate New England Road Trip Itinerary!

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4 comments

Cheryl Minervini July 24, 2019 - 09:47

This is great! Thanks, Jonathan

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Global Viewpoint January 16, 2020 - 09:50

Thanks Cheryl! Glad you enjoyed it 🙂

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Anonymous July 23, 2019 - 06:21

Thanks for this great article! I love spending my vacations in New England! Still so much to see for me, next trip will be to Martha’s Vineyard, soo excited

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Global Viewpoint July 23, 2019 - 09:29

So glad to hear it! Hope you have a wonderful trip! 🙂

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