Enjoy the Best Northeast USA Road Trips This Year

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When it comes to exploring the very best of the United States, there is no better way to accomplish this than by taking an epic road trip. We LOVE packing our car with the essentials and then heading out on a long weekend road trip to enjoy new parts of the US. From the east coast to the west and everything in between, the US is the perfect location and epitomizes everything there is to love about road trips. If you read our post on the best east coast road trips, you will know that we are very fond of the New England corridor. What better way to celebrate this beautiful part of the country than by highlighting the very best northeast USA road trips.

best northeast usa road trips

We are grateful to a collection of our friends in the travel blogging world for contributing to this epic post. We have been fortunate to enjoy a couple of amazing road trips in northeast USA over recent years, but when it comes to putting together a post highlighting the “best of the best”, we figured it was appropriate to call in the experts. Let’s take a look at some of the best road trips you can experience this year and of course, in years to come.

best road trips in new england

Best Northeast USA Road Trips

Whether you are exploring the neighborhoods of Boston or heading along the coast to explore the iconic lighthouses near Portland, the New England area is the perfect spot to enjoy a spectacular road trip. Breathtaking fall foliage, picturesque wintry scenes, gorgeous national parks and much more typify why this part of the US is such a popular region for road tripping.

boston common

Here is a collection of road trips that we are going to highlight throughout the post but this is just a small sample of the myriad of endless opportunities that exist in the American northeast.

  • Boston to Montreal – In 2014, we took a similar road trip from Boston to Quebec taking in all of the states in this part of the country before crossing the border into Canada.
  • Providence to Newport (Rhode Island)
  • Boston Figure of Eight – Cape Ann, Salem, Plymouth, Cape Code etc.
  • Scenic Route 100 Byway (Vermont)
  • Boston to Portland
  • Portland to Acadia National Park
  • New York City to Cape Cod
  • Hudson River Valley – head a little further inland from the New England corridor and the state of New York offers a collection of amazing road trip options, including this epic journey.
  • Finger Lakes (New York) – this is the “exception” to this list of New England road trips but it’s a short distance from this region offering spectacular scenery and so well worth including in this post.

Boston to Montreal

Click here to open Google Maps for details of this road trip between Boston and Montreal

boston to montreal map

On your way to Montreal drive up to New Hampshire and into the white mountains. Pull off the road to enjoy the views, hikes, and waterfalls of New Hampshire. If you have kids along enjoy Santa’s Village or Storyland and the cute ski town of Lincoln. 

garwin falls new hampshire

Take time to placate your sweet tooth with the world’s longest candy counter at Chutter’s in Littleton. Right before you reach the Canadian border you will find the Derby Line – you are halfway between the North Pole and the equator! You can even cross the border by walking through a library. This is the kind of kitschy stuff road trips are designed for. 

After visiting Montreal, head back to Boston through the artistic, rural state of Vermont. Take a tour at the Ben and Jerry’s Ice Cream Factory. Stop by the most charmingly New England town of Woodstock where you can shop, walk the town green and see its covered bridge. Also, stop by the nearby artists’ studios and farms; Hike the famous Quechee Gorge to see the best of fall’s colors. This drive will take about 10 hours and is the perfect way to experience New England.

quechee gorge

Thanks to Jamie Italiane from The Daily Adventures of Me for sharing this awesome road trip. Read on for more details about this road trip from Boston to Montreal.

Providence to Newport

Click here to open Google Maps for details of this road trip between Providence and Newport, Rhode Island

providence to newport map

New England is filled with history and great outdoors experiences, providing a plethora of travel opportunities to fit any nomad’s preference. But during the fall, the North Eastern coast of the United States erupts in beautiful hues of orange, brown, and every autumn shade imaginable. 

More specifically, Rhode Island acts as a perfect example of what the North East has to offer, and a short road trip from Providence to Newport allows you to take it all in. This is a short trip taking you through the more rural regions of Rhode Island and allowing you to take in all the foliage. 

rhode island

Your destination in Newport is where the fun begins, with some of the best seafood and eateries that you’ll find in the U.S., such as the Red Parrot Restaurant. 

marble house newport rhode island

When you decide to eat is on you, but maybe you’d prefer to explore the mansions on the Newport shores first? Regardless, be sure to take in both no matter how you plan it, as nothing beats an autumn scenic drive ending in engorging seafood and amazing architecture!

Thanks to Casey LaClair from Viraflare for sharing her thoughts on this scenic road trip in Rhode Island.

Boston Figure of Eight

Click here to open Google Maps for details of this road trip around the iconic locations in Massachusetts

boston to nantucket map

Boston offers so many intriguing road trips that the best thing to do is to loop a few together in a figure of eight on a map. Start by heading north to Cape Ann, the quieter side of New England. Look for breezy promenades, squat light houses and the home of deep fried clams.

cape ann massachusetts

Return to Boston, stopping in at Salem to look at the witch trials that featured in Arthur Miller’s The Crucible, then continue south. Stay overnight in Plymouth and grapple with the history of the Mayflower and the arrival of the pilgrims amid tranquil marinas and polished lawns.

ferry to martha's vineyard

From there continue into the hook of Cape Cod, her salty sand banks and calm waters. If time allows, take the ferry to Martha’s Vineyard and Nantucket, two different glimpses of life in America, each with their own charm.

Finally, return to Boston, with a quick detour to see the deep blood red of the cranberry bogs that lie along the side of the road. For further details on this journey, check out this road trip from Boston.

Thanks to Abigail King from Inside the Travel Lab for sharing this road trip featuring some of the best things to do in the state of Massachusetts.

Scenic Route 100 Byway

Click here to open Google Maps for details of this road trip along Scenic Route 100 in Vermont

route 100 vermont map

There are endless opportunities for road tripping in Vermont. The state has more dirt roads than paved and more cows than people. Route 100, which is Vermont’s longest state highway, runs 216.6 miles through the Green Mountains, from north to south. If you’re looking for a quintessential Vermont road trip, then Route 100 is the perfect place to start. 

Begin your journey in the small mountain town of Wilmington and head north through the Green Mountain National Forest. The road passes pristine mountain lakes, cascading waterfalls, secret swimming holes, and quite campgrounds. It is an awesome Vermont road trip for fall when you can take full advantage of the gorgeous fall colors and outdoor adventures in the mountains. 

vermont fall road trip
Somerset Reservoir in Green Mountain National Forest by Tara Schatz

Highlights of a Route 100 road trip include Jamaica State Park, where you can rent a cabin on the West River, the iconic Long Trail Brewing Company in Bridgewater Corners, and the beautiful mountain town of Stowe. Be sure to drive up the Mt. Mansfield Toll Road at Stowe Mountain Resort. At 4,395 feet, Mt. Mansfield is Vermont’s tallest peak, and the views from the top are incredible. 

vermont road trip
Kelly Stand Road off of Route 100 by Tara Schatz

After 216 miles of driving, Route 100 ends in the bustling little city of Newport, where you can take a sunset cruise on Lake Memphormagog, eat traditional Thai food at Dusit Thai Cuisine, and shop the local boutiques on Main Street.

Thanks to Tara Schatz from Back Road Ramblers for highlighting some of the lesser known spots worth exploring in the New England area in the state of Vermont.

Boston to Portland

Click here to open Google Maps for details of this road trip along the New England coast between Boston and Portland

boston to portland map

Many have heard of Salem, Massachusetts because of its’ haunted history of witchcraft hysteria in the 1690s and witch trials. With hundreds of thousands of visitors every year, there is no doubt that this is a must on your road trip from Boston, Massachusetts to Portland, Maine.

With many haunted happenings no matter the time of year, the best time to visit Salem is in the fall for the biggest effect. No visit to Salem would be complete without visiting at least one of the following three attractions. The Witch History Museum is where to go to hear all the stories of witch trials and witch craft in Salem. 

Following your visit to the museum head to the Witch House, which is the only building in Salem still standing with direct ties to the Salem Witch Trials. The house was owned by Judge Jonathan Corwin who was the judge of the Salem witchcraft trials. It is believed that some interrogations even took place here!

house of seven gables

On a less spooky note, Salem is also home to Nathanial Hawthorne’s “The House of the Seven Gables” which offers tours and gives you a picture into what life was like in the 1800s. Salem is a culturally rich and haunted gem of the USA definitely worth your time. 

Thanks to Sarah Fay from Travels of Sarah Fay for highlighting why the iconic town of Salem is a must-see during your road trip from Boston to Portland. When you arrive in Portland, don’t forget to explore the historic Portland Head Light along with other lighthouses along this stretch of coastline.

Portland to Acadia National Park

Click here to open Google Maps for details of this road trip from Portland to Acadia National Park along the coast of Maine

If there’s one thing Maine is definitely good for its road trips and after road-tripping the entire Maine coastline, I’d highly suggest driving from Portland, Maine to Acadia National Park in Maine. There are plenty of things to do along the way, plenty of sites to see, places to eat, and much more that you could spend weeks along this route and still not see it all. But, of course, there are always highlights. 

portland head light

Starting in Portland, make sure to check out one of the most beautiful lighthouses, Portland Head Lighthouse, eat at Green Elephant in the city, grab donuts at Holy Donuts, and walk around Mackworth Island. 

Next stop is Damariscotta to grab a bit and check out the small town before heading to Pemaquid Lighthouse (make sure to go up in the lighthouse – it’s one of the few you can!). Then head to Marshall Point Lighthouse to see the lighthouse from Forrest Gump! 

pemaquid lighthouse

Keep heading along the coast stopping in Rockland for cool street art, shopping and restaurants and then head up to Camden Hills State Park for beautiful, panorama views and hiking. The last leg of this road trip includes a stop in Deer Isle for a unique and off the beaten path vantage of Maine – drive around the entire island making leisurely stops along the way and soak up what feels like a step back in time – and a stop in Bangor to scope out all the cool Stephen King locations and a cool, sleepy New England town.

acadia national park

While in Acadia National Park, make sure to check out all the amazing hikes (I highly suggest the Wonderland and Ship Harbor Trail), take day trips to Bar Harbor to explore this adorable town and take a whale watching tour, and go kayaking around the many little islands. 

Thanks to Ashley Hubbard from Wild Hearted (also, Oddities and Curiosities) for sharing this amazing road trip along the Maine coastline.

New York City to Cape Cod

Click here to open Google Maps for details of this road trip along the coast of Connecticut, Rhode Island and Massachusetts

new york to cape cod map

A road trip from New York City along the coastline of Connecticut, Rhode Island and the Cape Cod section of Massachusetts in the autumn is a great idea because the weather is still pretty warm yet the crush of the summer tourist season is finished. Autumn color blooms along this route by mid-October as well. 

yale university new haven

There are quite a few historical places to visit on this road trip. In Connecticut be sure to visit New Haven which is famous for Yale University (and Louis Lunch which is the reputed birthplace of the hamburger) and Mystic which has a renowned aquarium and living history museum. Mystic skyrocketed to fame in the 1980’s for the movie, Mystic Pizza, which was one of Julia Roberts’ first major hits. Mystic Pizza still exists and is totally worth a visit. 

newport rhode island

In Rhode Island, be sure to stop off in Newport and visit the summer “cottages” of the super rich elite of the Gilded Age. Newport also has a charming harbour and is home to the International Museum of Tennis. 

In Cape Cod and the Islands (Martha’s Vineyard and Nantucket), you will find autumn is a great time for cycling, hiking, and fishing – pretty much every outdoor activity available during the more expensive summer months except for beach going.

cape cod

Make sure not to miss the cranberry bogs in the area as well. Some of the local fall festivals include the famous Wellfleet Oyster Festival, Oktberfest in Chatham or the Martha’s Vineyard Food and Wine Festival in Edgartown.

Thanks to Shobha George from Martha’s Vineyard Tourist for sharing this awesome road trip along the New England coastline.

Hudson River Valley

Click here to open Google Maps for details of this road trip along the Hudson River Valley

hudson river valley map

When it comes to fall leaf-peeping destinations, New England tends to get all the attention. But as a native New Yorker, I promise the Empire State’s fall foliage is just as gorgeous. The best way to do a New York State fall road trip is to do a big loop, starting and ending in New York City.

Along the way, you should visit the cutest towns along the Hudson River. The best town for hiking and antiquing is Cold Spring. Before heading out on a hike, stop at Hudson Hill’s, famous for its chocolate french toast. 

beacon new york

Another great town is Beacon, where you can find Dia Beacon, a contemporary art museum as good as any in New York City. After the museum, eat at Brother’s Trattoria, a cozy Italian restaurant. If you feel like getting into the Halloween spirit, stop by Tarrytown. The author of The Legend of Sleepy Hollow, Washington Irving, lived here, so the town goes all out with pumpkins, skeletons, and headless horsemen every year. 


Finally, history buffs and foodies shouldn’t skip Poughkeepsie. Tour the home of Franklin Delano Roosevelt and then dine at the Culinary Institute of America, where Anthony Bourdain studied cooking. The Hudson River Valley has something for everyone.

Thanks to Stella from Around The World in 24 Hours for sharing this awesome New York road trip. We have previously taken a day trip from New York City to Bear Mountain, in the heart of the Hudson Valley and can attest that the scenery here is breathtaking.

Finger Lakes, New York

Click here to open Google Maps for details of this road trip around the Finger Lakes in New York

finger lakes road trip

Western New York is especially beautiful in the fall. The weather gives way from hot summers to crisp mornings and evening and temperatures ready for jeans and t-shirts on a warm day or light sweaters in early fall. You can spend just about a week on a road trips to the Finger Lakes with two days in each of these these locations: 1) Corning, 2) Watkins Glen, 3) Chemung County. If you have time, add Hammondsport to your Finger Lakes itinerary.


The Corning Museum of Glass and Rockwell Museum are a must before leaving Corning to explore the beauty of the Finger Lakes region.

corning glass museum

Watkins Glen

This is the perfect city in the Finger Lakes for a romantic weekend getaway. Their state park is a must see experience! It’s absolutely stunning and you can take an enjoyable, easy hike there. A sunset sailboat ride with Schooner Excursions around Seneca Lake is a great idea if it’s the right time in the season.

watkins glen waterfall

Chemung County

The National Soaring Museum is incredibly interesting and if you visit at the right time, you can take a hang glider ride from the same location in Elmira. This area is also deemed “Mark Twain Country,” where he spent many summers writing and enjoying the area.

national soaring museum

He famously wrote The Adventures of Tom Sawyer and The Adventures of Huckleberry Finn at his study, which is available for the public to visit at Elmira College. For those of you that have visited Twain’s boyhood home in Hannibal, Missouri, this will be a perfect place to visit to learn more about his iconic works.


If you have time be sure to travel the short distance to nearby Hammondsport as well. Dr. Frank’s is a winery that offers tastings and a beautiful view of their vineyards in the area. We recommend taking a seaplane ride with Finger Lakes Seaplanes over Keuka Lake too. It’s especially splendid during fall! 

Thanks to Mikkel from Sometimes Home for sharing a part of New York that we are particularly excited about visiting in the near future.


Road tripping around the New England states offers a little bit of everything, with an eclectic blend of urban beauty mixed in with breathtaking rural bliss. Whether you are intrigued by the myriad of lighthouses along the coastline or perhaps want to learn all about the history of the Salem witches, planning a road trip around northeast USA is always going to offer plenty of opportunities for amazing experiences.

We think the above collection of road trips offers a diverse blend of experiences and we want to thank each and every travel blogger for contributing to this post. We look forward to adding other northeast USA road trips to this post in the future, so please feel free to share your favorite trips in the comments section below.

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Chris Boothmanhttps://abritandasoutherner.com
Chris Boothman is the co-founder of A Brit and A Southerner. Born near Manchester, England, Chris moved to USA in 2006 where he soon after met his wife and travel partner in crime, Heather. They have since embarked on an amazing journey of travel as they challenge others to follow in their paths of working full-time but also being able to travel frequently! If you have any questions or comments, please feel free to contact Chris at [email protected]


  1. road trip is my weakness, and i can die for any of road trip. This article is very useful, hence last week i just reach north america after 1000 km trip by bike. Your article also inspired me to do again, i am planning for new trip, and very soon i will be start. Your photos are really nice…


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