9 Gorgeous New England Road Trips You’ll Want to Take This Year

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Itching to set off on a good, old-fashioned road trip? Then New England is just the place for you. Whether you’re on the hunt for an epic hike, taking in the history of some of America’s oldest towns, or simply enjoying the views, New England road trips offer something for everyone. 

Best New England Road Trips | Enjoy Travel Life

CONTENT – In this article, you’ll learn all about the best places to go on road trips in New England, including:

The Best New England Road Trips 

One of the best parts about New England road trips is that they are beautiful no matter what season you decide to visit. 

In the fall, you can expect to see the leaves turn into fiery shades of orange and red.

Wintertime blankets the coast with lovely snow.

And the forests come to life in New England’s spring and summer months. 

So, we’ve rounded up nine of the top New England road trips to spark your travel bug and help you plan the perfect trip up north. These New England trip ideas are sure to pique your interest when you’re planning road trip to the northeast.

The only trouble you’re likely to have is deciding which one to take first.

1. Kancamagus Highway in New Hampshire

Kancamagus Highway Road Trip | Enjoy Travel Life

Start: Conway, New Hampshire

End: Lincoln, New Hampshire

Distance: 34 miles

Must-See Attractions: Flume Gorge – Hike along boardwalks and paths through this 800-foot gorge with soaring waterfalls in Lincoln NH. You’ll enjoy beautiful woodland scenes and waterfalls at the base of Mount Liberty, which is part of the White Mountains.

Related: White Mountains: 3 Fantastic Inns in Bethlehem NH You Will Love!

Kancamagus Highway Road Trip Route

Kancamagus Highway (pronounced “Kank-ah-mah-gus”) is one of the most popular road trips in New Hampshire.

Not only does this road trip offer beautiful views for leaf-peepers in the fall, but with many natural wonders along the way, it makes for a gorgeous road trip year-round. 

A typical trip will take about half a day. But, it could last longer if you choose to pack in a few hikes or spend more time at some of the scenic stops along the way such as Swift River and the Albany Covered Bridge

You should also try to see the Sabbaday Falls on the way to Conway NH. It’s one of the most-visited waterfalls in New Hampshire.

After a quick 10-minute walk from the parking lot to the base of the falls, you’ll be able to take in the 45-foot waterfall that cascades into the pool below. 

There’s also a picnic area and a restroom there, making this a perfect place to stop for lunch or a snack as you explore New Hampshire. 

Related Article: What You Should Pack for Fall in New England [Checklist]

2. Mohawk Trail in Massachusetts | New England Road Trips

Berkshires Road Trip | Enjoy Travel Life

Start: Athol, Massachusetts

End: Williamstown, Massachusetts

Distance: 63 miles

Must-See Attractions: Natural Bridge State Park – This park in North Adams, MA features woodland trails with views of a dam made of white marble and an old marble quarry. In fact, it’s the only natural white marble arch in North America!

Mohawk Trail Road Trip Route

The beautiful stretch of highway known as the Mohawk Trail once served as a trade route that connected Native American tribes along the Atlantic coast. 

Like most scenic trails in the northeast, the fall invites many a foliage fan to view the fiery landscape of the changing leaves.

However, no time of year is a bad time to catch the views of the Berkshires and the Taconic Mountains.

You’ll discover exceptional hiking trails dotted throughout the 63-mile trip.

One attraction that you should try to carve out time for is the Poet’s Seat Tower near Greenfield, Massachusetts. The Poet’s Seat Tower sits atop a 190 million year old basalt lava flow offering sweeping views of the Connecticut, Deerfield, and Green River valleys.

You’ll also find plenty of quaint inns and restaurants to rest after a long day of exploration. 

You could even stop by one of the many maple syrup farms in the area for a unique souvenir as a remembrance of your northeast road trip.

TIP: If you want to extend this New England road trip a little further beyond Williamstown, you can continue on to Stockbridge for a visit to the Norman Rockwell Museum. While you’re in the area, grab a bite at the historic Red Lion Inn Restaurant and stay over at the Inn at Sweet Water Farm, a charming bed & breakfast in the nearby village of North Egremont.

3. Coastal Byway in New Hampshire

Portsmouth NH Road Trip | Enjoy Travel Life

Start: Seabrook, New Hampshire

End: Portsmouth, New Hampshire

Distance: 22 miles

Must-See Attractions: Whale watching – Choose from many whale-watching tours along the coastline that offer tour-goers the chance to spot humpback, finback, and minke whales. The best time for New England whale watching is May through October.

NH Coastal Byway Road Trip Route

While there’s something magical about driving through the dense forest land of the northeast, the coast offers its own special appeal. One claim to fame on New Hampshire’s coastline is that it’s the country’s shortest coast of any state.

As you travel along the coast, you’ll see everything from towering mansions to inviting beaches. While it’s a short drive, you’ll want to stop plenty of times throughout the byway to take in all that the area offers.  

We suggest you:

  • Take a walk by the ocean
  • Eat fried dough at Hampton Beach
  • Take a boat tour on the Atlantic Ocean
  • Visit historic forts and mansions
  • Sip on a craft beer in Portsmouth

You’ll find there’s something for everyone along this beautiful coastal New England road trip through New Hampshire. And if you have the time, definitely plan to stay over in Portsmouth. Here’s a lovely Portsmouth boutique hotel I stayed at that you might like, too!

Related: These are the Best Things to Do in Portsmouth NH

4. Old King’s Highway in Cape Cod

Cape Cod Road Trip | Enjoy Travel Life

Start: Sandwich, Massachusetts

End: Orleans, Massachusetts

Distance: 34 miles

Must-See Attractions: Scargo Tower – Located in Dennis, this tower is about 30 feet tall and boasts gorgeous views of Cape Cod’s hills. On a clear day, you can see all the way down to Provincetown.

Old King’s Highway – New England Road Trips Route

If you’re on the hunt for a truly historic road trip, Old King’s Highway is perfect for you.

Also known as Cape Cod’s Route 6A, Old King’s Highway is one of America’s most iconic byways and travels through the largest contiguous historic district in the United States. 

In 2021, Old King’s Highway achieved National Scenic Byway Status, making it one of only four in the state of Massachusetts.

The trip starts in historic Sandwich, Massachusetts, which is the oldest town on Cape Cod dating back to 1639.

There, you’ll find the Sandwich Glass Museum known for its unique glass treasures, the Dexter Grist Mill, and Hoxie House, which is one of the oldest houses on the Cape and is open for tours where you can see original period decor. 

As you wind through the Cape, you’ll see many historic attractions like:

  • Yarmouth New Church in Yarmouth
  • Drummer Boy Park in Brewster
  • French Cable Station Museum in Orleans

This is a perfect trip for history buffs! 

Of course, on Cape Cod, you’ll want to stop for some time at the beach and get some of the freshest seafood. Raw oysters, clam chowder, fried clams, and lobster rolls are local favorites.

You could also stop at one of these excellent Cape Cod Breweries along the way for a refreshing drink.

And if you’re traveling as a family, the Sesuit Harbor House in Dennis is a must-stay resort on the Cape that offers fun for the entire family.

Related: Click here to learn which towns in Cape Cod are the best to visit.

5. Park Loop Road in Maine

Park Loop Road Trip | Enjoy Travel Life

Start: Bar Harbor, Maine

End: Bar Harbor, Maine

Distance: 27 miles

Must-See Attractions: Cadillac Mountain – The loop winds up to the top of Cadillac Mountain, which is the highest peak in the park and the east coast of the northeastern US.

Park Loop Road – Road Trip Route

Park Loop Road is the primary road for navigating Acadia National Park. Whether you go during the snowy New England winter or as the leaves are changing color in the fall, Acadia National Park offers breathtaking views no matter what time of year you visit. 

There are many ways to explore the 27-mile stretch through the park.

Here are some great options to consider:

  • Drive yourself
  • Book a guided bus tour
  • Ride the Island Explorer shuttle bus

TIP: Be aware that during the peak summer months, the park can get very crowded so expect delays as you’re traveling the loop. 

On your way up to Bar Harbor, you might want to add a stop or an overnight in Portland Maine.

Related Article: What to Pack for Summer in New England

6. Providence to Newport in Rhode Island

Cliff Walk Newport RI | Enjoy Travel Life

Start: Providence, Rhode Island

End: Newport, Rhode Island

Distance: 33 miles

Must-See Attractions: The Breakers in Newport, RI – This opulent mansion is perhaps the most impressive of the Newport Mansions, which served as summer “cottages” for the rich and famous during The Gilded Age (1870-1890).

Providence/Newport Road Trip Route

Rhode Island may be the smallest state in the US, but its offerings are mighty.

From the grand Capitol Building in Providence, to the architectural luxury of the 11 Newport mansions, this New England road trip belongs on your bucket list.

Providence is a vibrant city, rich with a rich culture, outdoor spaces, and plenty of art.

It’s home to the world-renown art school, Rhode Island School of Design, so you’ll have no trouble finding art galleries, open studios, and silversmiths here.

The city also boasts a diverse food culture.

So, make a stop (or two!) in Providence’s “Little Italy,” Federal Hill, for a taste of delicious Italian food. You might also like to visit Plant City, the world’s first plant-based vegan food hall and marketplace.

There’s plenty to explore on foot in Providence, but if you’re visiting Providence in the summer, you might time your trip to coordinate with Gallery Night. These walking tours guided by local experts showcase some of the best galleries in Providence.

Or, take in Firewater.

This public art display sets the Providence River ablaze at night and is truly surreal. You can sit along the river’s edge or take a gondola ride to be closer to the experience.

From Providence, head south and cross the Jamestown and Verrazano bridges to reach Aquidneck Island. You’ll arrive in Newport, where you’ll find soft-sand beaches, upscale shopping, and waterfront eateries at Bowen’s Wharf.

Fun Things to See and Do in Newport

Some unique stops you might want to make while you’re exploring Newport include:

  • The International Tennis Hall of Fame
  • Audrain Auto Museum
  • National Museum of American Illustration

And of course, you must visit the Newport Mansions. They are especially beautiful over the winter holidays, when each mansion is dressed in luxury for the holiday season.

Another good way to get a look at the mansions and their well-coiffed grounds is to walk along the Cliff Walk.

This free 3.5 mile walk flanks the coast and gives view to the Atlantic ocean on one side, and the expansive grounds and exterior architecture of the Newport Mansions.

TIP: While you’re on Aquidneck Island, take a scenic drive to explore the bucolic farms and winding roads of Portsmouth and Middletown. This tiny island is home to two fantastic vineyards, Greenview Vineyards (Portsmouth) and Newport Vineyards (Middletown). Stop in to either and enjoy a refreshing glass of wine. You can take a few bottles home as a remembrance of your trip!

7. South Coast to Block Island in Rhode Island

Block Island RI Road Trip | Enjoy Travel Life

Start: Wickford (North Kingstown), Rhode Island

End: Westerly, Rhode Island

Distance: 31 miles

Must-See Attraction: Watch Hill Carousel – This colorful, lighted amusement ride in Westerly is thought to be the only remaining flying horse carousel. That means the horses, suspended by the chain from the center of the carousel, radiate out as it turns. 

RI South Coast Road Trip Route

Begin this coastal New England drive in Wickford Village, a historic community on the harbor located a half-hour outside Providence.

Wickford hosts an annual summer Art Festival, but any time of year you visit, you’ll find:

  • Art Galleries
  • Unique shops and boutiques
  • Outdoor cafes

Next, head over to Narragansett Beach for a beach break. The waves are big here, so you can watch the surfers “hang ten,” or even take a surfing or paddle board lesson yourself.

Head south to Point Judith, where many local restaurants source delicious Point Judith Calamari.

One place to stop for a bite is George’s of Galilee, a clam shack overlooking Block Island Sounds where you can enjoy local favorites like Calamari or Portuguese Clams with Chorizo.

Then, take the high-speed Block Island Ferry at Galilee for a 30-minute sunset ride to Block Island. It’s best to leave your car behind and rent bikes on the island.

The National Hotel is a lovely Victorian and the flagship of the island. It’s also the most convenient lodging from the ferry if you plan to spend the night on the island. You’ll want to take the time to visit the unique shops and galleries scattered in New Shoreham.

You can even pack a picnic lunch from Finn’s Seafood Restaurant to take with you.

Fun Things to Do on Block Island

Some natural beauty on Block Island you’ll want to see includes:

  • Mohegan Bluffs
  • Settlers Rock
  • the nature trails throughout Block Island

Or, just relax at any of the pristine beaches along Block Island’s 17 miles of shoreline before taking the ferry back to the Rhode Island mainland. 

When you return to the mainland, have a look at the Watch Hill Carousel in Westerly. It’s thought to be the oldest continuously running carousel in the US.

Next, head over to Saunderstown to the Gilbert Stuart Birthplace and Museum.

You can take a tour of the museum, which is set within a historic restored 1750 home and celebrates the work of Gilbert Stuart. This prolific portrait artist painted six sitting presidents!

Make a stop at Sweet Cakes in Peace Dale, a tiny village in North Kingstown, where you can enjoy a delicious coffee and pastry in their quaint patio. Take some vegan cookies or a sandwich to-go for the ride home.

8. Scenic Route 100 Byway in Vermont

Vermont NE Road Trip | Enjoy Travel Life

Start: Wilmington, Vermont

End: Newport, Vermont

Distance: 213 miles

Must-See Attractions: The Trapp Family Lodge (Stowe) – Tour the famous home and sweeping mountain vistas made famous by the movie, The Sound of Music.

Vermont Route 100 Road Trip Route

You can traverse the Scenic Route 100 Byway in Vermont a little over half a day, but you’ll want to turn this trip into at least a long weekend since there’s so much to see and do.

The route along nearly the entire length of the “Green Mountain State” follows the eastern edge of the Green Mountains, ending at the Canadian border.

Summer is an ideal time to take this New England road trip, since in the winter attracts tourists to Vermont ski resorts—unless you ski.

In that case, you’ll find plenty of ski resorts located right along Route 100. In summer, you’ll want to hike any of the trails along the way to enjoy Vermont’s fresh air, woodland settings, and pristine waterfalls. And of course, the fall foliage is stunning!

In fact, Yankee Magazine calls this route “the most scenic in New England” so get ready to take some great travel photography!

A few of the stops you’ll want to consider on the Route 100 Scenic Byway include:

  • Appalachian/Long Trail (Stamford)
  • Atherton Meadows Wildlife Management District (Whitingham)
  • Wheeler’s Farm (Whitingham)
  • Carinthia Ski Area (West Dover)
  • Catamount Trail (Dover)
  • Jamaica State Park (Jamaica)
  • Magic Mountain Ski Resort (Londonderry)
  • West River Fishing Stream (Weston)
  • Buttermilk Falls (Ludlow)
  • Lake Pauline (Ludlow)
  • Vermont Country Store in Weston – free cheese and maple syrup samples
  • Coolidge State Forest (Plymouth)
  • Thundering Brook Falls (Killington)
  • Vermont River Tubing (Stockbridge)
  • Green Mountain National Forest (Rochester)
  • White River Golf Club (Rochester)
  • Granville Gulf State Reservation (Granville)

Impromptu Stops to Make in Vermont

Part of Vermont’s natural beauty means you’ll enjoy seeing wildlife in these bucolic settings.

In fact, keep your eyes peeled for moose, often seen by the roadside, especially the further north you go. This is important because they can be dangerous to motor vehicles if they cross your path.

Along the way, you’ll be tempted to make many impromptu stops.

They may include fine dining, antiquing, touring galleries, artisan, and antique shops, or checking out breweries and farm stands. This Vermont road trip is an adventure that will present you with many opportunities to explore, to allow plenty of time for it in your itinerary.

Covered bridges and chainsaw carvings are some other regional specialties you’ll want to watch for as you travel route 100.

And be sure to get yourself some genuine Maple Syrup (and maybe some Ben & Jerry’s ice cream) while you’re in the area!

9. Shoreline Route in Connecticut

Old Saybrook CT | Enjoy Travel Life

Start: Stonington, Connecticut

End: Old Saybrook, Connecticut

Distance: 35 miles

Must-See Attractions: Gilette Castle (Lyme) – This stone structure was originally the private residence of William Gillette, best known as the actor who played Sherlock Holmes on stage. This 3.5 floor, 24 rooms “castle” overlooks the river and has a number of oddities, like trick locks and a hand-carved bar with a secret latch.

Coastal Connecticut Road Trip Route

This coastal Connecticut route from Stonington Connecticut to Old Saybrook can be a quick trip along the highway, but we suggest you meander along the coastline instead.

Mystic is a historic shipbuilding village in Connecticut where you can enjoy shops, restaurants, and waterfront scenes on the Mystic River. Movie buffs will remember the movie Mystic Pizza (1988) shot on location and in nearby towns.

A visit to the Mystic Aquarium pairs perfectly with your coastal road trip theme.

This small town can get busy in the summer, so be prepared to wait your turn for attractions and local restaurants. You can head over to Stonington Borough, which is quaint and more compact than Mystic, but just as charming.

Stops Between Old Lyme to Saybrook, Connecticut

Next, head over to Old Lyme and stop for homemade ice cream at the Old Lyme Ice Cream Shoppe. You can enjoy your treat beneath the shade trees on Main Street.

Watch for art exhibits and presentations at the Lyme Art Association

Tour the Gilette Castle, a small but incredible stone castle that sits high about the Connecticut River, straddling Lyme and East Haddam.

Then, take a quick but scenic Hadlyme ferry ride that departs from Gilette Castle State Park to Chester. The original ferry was pushed across the ferry using poles. This one is powered and can accommodate cars and passengers.

In the historic town of Essex, check out the Connecticut River Museum and then make your way over to Old Saybrook.

This picturesque Connecticut town offers shopping, strolling, and excellent dining opportunities.

We recommend getting a delicious cappuccino and authentic Italian fare at James Pharmacy Bed & Breakfast. If you have the time, stay over at this boutique inn, or next door at The Deacon Timothy Pratt Bed & Breakfast. Both are excellent options.

Finally, enjoy the views at the marina at Saybrook Point.

Final Thoughts on Planning Your New England Road Trips

While you’re packing and choosing the perfect road trip snacks, don’t forget to inspect your car to ensure it’s in tip-top shape before hitting the road. 

In the winter, be sure to pack an emergency kit containing items that will keep you warm in case you’re out of cell range. 

And in the summer months, be sure to check off this summer car maintenance checklist that will help prevent a tire blowout or broken AC that can seriously damper the road trip mood. 

Don’t forget to save this article for later on Pinterest!

scenic new england road trips pin | Enjoy Travel Life
new england road trips pin | Enjoy Travel Life

Author Bio 

Lydia McAllister is a content creator who develops helpful and compelling stories. Her passion for digital marketing and creative writing has led her to cover unique topics ranging from business to lifestyle. She calls Texas home and enjoys burying her nose in a good book, exploring new locales and spending time with family in her spare time.

Editors Note: The original post has been expanded.

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