Road trips are one of the best ways to travel, particularly in New England. The Northeastern part of the United States is filled with small towns and national parks that are often overlooked by big, bustling cities, like New York City and Boston. And, that’s truly a shame, because these hidden gems deserve to be enjoyed! All you need is a New England road trip itinerary and you’re bound to have a good time!
The best New England road trips offer a combination of big cities, small towns, and nature stops. So while one day, you may be strolling along Boston’s Freedom Trail, the next you might be exploring the quaint town of Newport, Rhode Island.
In this post, I have come up with an amazing 10 day New England road trip itinerary. This plan will ensure that you see so much of the beauty that New England has to offer. That said, feel free to rework this itinerary to fit your preferences and style of travel.
In This Post:
The Perfect New England Road Trip Itinerary
When starting your epic New England road trip, I recommend flying into Boston Logan International airport. This airport is huge and is a major hub for several airlines in the States. Plus, you can easily rent a car here to start your road trip.
Or, you can drive to New England from where you live if you’re a road trip kind of person and are feeling adventurous. Don’t forget to check out my road trip packing list and make sure you have these 20 items before starting your adventure!
Days 1 and 2: Boston, Massachusetts
Many of the best New England road trip itineraries begin in Boston. Thanks to the Logan International Airport (KBOS), it’s quite easy to find a flight into Massachusetts’ capital city, whether you’re traveling from within the United States or from abroad.
After you land in Boston, Massachusetts you simply can’t pass up the chance to see this historical city. It’s the capital of one of the US’ original thirteen colonies, after all. Learn a little about the American Revolutionary War at the Bunker Hill Monument, ride on the first subway system ever built in the country, and wander along the Freedom Trail to see all the historic sights.
Not all of the attractions in Boston center around history. Embrace your inner mad scientist at the Museum of Science, peruse the pieces at the Museum of Fine Art, get some fresh air at the Boston Public Garden, or grab a pint from the Samuel Adams Brewery.
Day 3: Providence, Rhode Island and Newport, Rhode Island
On the third day of this New England road trip itinerary, you’ll stop at two of the best towns in Rhode Island. As the smallest US state, Rhode Island often gets overlooked, but it’s definitely worth your time.
As the capital of Rhode Island, Providence has quite a few things to do. Spend some time at Roger Williams State Park, grab a delicious meal in Little Italy, and savor an authentic French dessert from Pastiche. And if you happen to be in Providence in the summer, catch the unique attraction known as WaterFire, during which dozens of bonfires in the center of Providence River are lit.
After you’re done in Providence, make the short 45-minute drive to the adorable town of Newport. Or, if you fall in love with Providence, you can opt to spend a night there and then go to Newport the next day. I’m guilty of changing up my road trip itineraries last minute so change things up as much as you want!
While in Newport, enjoy a little bit of downtime. Stroll along the waterfront Newport Cliff Walk and do a little shopping on Thames Street.
Day 4: Mystic, Connecticut
Like Newport, Rhode Island, Mystic, Connecticut is a lovely little seaside town. While there aren’t a ton of things to do in Mystic, this is the perfect stop to take a breather on your New England road trip itinerary. After all, your first three days were packed with excitement – and there’s only more to come!
That said, the few things there are to do in this adorable town revolve around water. Learn about the United States’ maritime history at the Mystic Seaport Museum & Village. See hundreds of amazing sea creatures, including beluga whales, sand tiger sharks, and cownose rays at the Mystic Aquarium. You can even spend a day on the beach at Napatree Point.
Don’t forget to stop by Mystic Pizza while you’re in Mystic. This pizza joint caught the eye of Hollywood and it became a setting for the movie “Mystic Pizza.”
Day 5: Litchfield Hills, Connecticut
Litchfield Hills is the first of the nature-focused stops on this New England road trip itinerary. While this amazing area is best in the warmer months, you can still find things to do in Litchfield Hills in the winter as well.
One of the most popular things to do in Litchfield Hills is to tackle a hike. The Appalachian Trail cuts right through this Connecticut town, and you can hike part of this iconic path! As an alternative, you can make your way along the Campbell Falls trail, which actually crosses the border from Connecticut to Massachusetts.
Other than the hikes, you can also go fruit picking at Ellsworth Farm, see some of the best fall foliage in the country at Lake Waramaug, and grab yourself a scoop or two of ice cream from Arethusa Dairy. And if you do find yourself in Litchfield Hills during a bout of snow, you can ski at Mohawk Mountain and ride a snow tube at Woodbury.
Day 6: Montpelier, Vermont and Stowe, Vermont
The drive from Litchfield Hills, Connecticut to Vermont is the longest drive of this New England road trip itinerary at approximately four hours long. But, that drive is definitely worth it because you’ll get to see the gorgeous Green Mountain National Forest on the way and stop by two of Vermont’s most beautiful cities: Montpelier and Stowe.
Other than being the capital city of Vermont, Montpelier is known for two main things: food and nature. As for the food aspect, this city is home to an apple cider mill, tons of maple syrup farms, and even Ben & Jerry’s ice cream factory. And as for nature, hike up the mountain known as the Camel’s Hump, explore the granite quarry known as the Rock of Ages, and do a little leaf-peeping in autumn.
If you happen to be tackling this New England road trip itinerary in the fall, be sure to add Stowe, Vermont to your plans as well. While in this adorable town, you can drive, hike, mountain bike, kayak, and take a guided tour through the fiery autumn leaves.
Day 7: White Mountain National Forest, New Hampshire
As you drive from Stowe in Vermont to the White Mountain National Forest in New Hampshire, you’ll want to drive through an area known as the Smuggler’s Notch. Despite what its name may suggest, the Smuggler’s Notch is a curving road through beautiful mountains. While in the spring and summer, they are a lovely bright green, you can also catch the warm colors of fall, and the snow-capped tops of winter.
Soon after that, you’ll find yourself in the gorgeous White Mountain National Forest. Obviously, what you do in the national forest depends upon the time of year. In the warmer months of spring and summer, you can hike and bike over miles of trails. In the fall, you should definitely stare in awe at the fall foliage while driving along the Kancamagus Scenic Byway. And in the winter, ski, snowshoe, and sled to your heart’s content.
While you won’t be able to stay within the White Mountain National Forest, you will be able to stay in the nearby town of Lincoln. This area also has a few things to do, including hiking through Flume Gorge, skiing down Loon Mountain, and grab a beer at One Love Brewery.
Day 8: Acadia National Park, Maine
The most nature-focused New England road trips always include Acadia National Park. After all, it is one of the most stunning national parks in the entire country and one of the best places to visit in Maine.
While at Acadia National Park, there’s no shortage of things to do. Wake up early to catch the sunrise from Cadillac Mountain. Tackle the Beehive Hike, a relatively easy hike that is a visitor favorite. Drive around the Park Loop Road and admire the scenery. Maybe even do a little rock climbing at Otter Cliff.
Honestly, there are so many wonderful activities in Acadia National Park that you may be tempted to extend add a day to this road trip stop – and that’s totally okay!
Just like the White Mountain National Forest, you won’t be able to stay within Acadia National Park. Luckily for you, the popular town of Bar Harbor, Maine is right next door.
There are so many things to do in Bar Harbor Maine, such as going on a whale-watching tour, doing a little bird watching at Frenchman Bay, and stopping to smell the flowers at the College of the Atlantic Gardens.
Day 9: Portland, Maine
As one of the most beautiful states in the US, Maine certainly deserved two stops on this New England road trip itinerary. Similar to its name counterpart of Portland, Oregon, Portland, Maine has a cool hipster vibe, many delicious restaurants, and an absurd number of breweries. Be sure to take advantage of all of the trendy spots this amazing town has to offer.
In addition to food and drink, Portland, Maine has quite a few attractions that are worth your time. Wander around the Old Port, take a ferry to visit Peaks Island, and pay a visit to the Portland Head Light.
I also highly recommend taking a day trip to the nearby charming small town of Kennebunkport. There are so many incredible things to do in Kennebunkport Maine and it’s the perfect escape from the hustle and bustle of Portland.
Day 10: Boston, Massachusetts
You made it! You just completed an epic road trip around New England! On day ten of your New England road trip itinerary, drive yourself back to Boston, Massachusetts. You can hang out in the city for a few more days, or you can fly back home through the Logan International Airport (KBOS) right away.
Best Time to Visit New England
New England is gorgeous to visit all year round, but the drives are easier during summer and fall. The fall foliage in New England is stunning and worth seeing! The best time to catch these vibrant colors is from late September through the end of October.
It’s not impossible to have a winter adventure in New England, but it will be challenging. It can get really snowy so make sure your car has reliable snow tires and you keep an eye out for the weather and any road closures. If you’re keen on going during winter, try to go during Christmas time so you can experience a Hallmark movie in real life.
No matter when you go, you’ll have a wonderful and memorable experience on your New England road trip.
What is your favorite New England road trip itinerary? Let me know in the comments below!
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Disha Smith is the founder of Disha Discovers. She quit her job in 2017 to travel the world to explore new cultures and experience new adventures. She has since been to 95+ countries and counting and has lived in South Africa, Thailand, Croatia, and Australia. She has done all kinds of travel ranging from luxury to budget backpacking, and her mission is to inspire others to discover their own sense of adventure and to help them plan a life full of meaningful experiences through travel.