Unforgettable New England road trip itinerary

  • Post last modified:September 23, 2023
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The New England road trip is a beautiful journey through one of the most appreciated parts of the United States. Touring the loaded Northeast, you face jaw-dropping nature, charming towns and proud tradition. So buckle up, this ultimate New England road trip itinerary contains all the gems you don’t want to miss in the lovely Northeast region.

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  • Total distance: 1217 mi / 1959 km
  • Total driving time: 23.5 h

1. Boston, MA – The New England road trip starts in Boston

The New England road trip starts in the City on a Hill, Boston. Massachusetts‘ largest city is certainly a convenient place to begin a Northeast road trip.

Many visitors, both national and international, arrive at Boston’s well-connected Logan Airport. Boston is also a city with a good selection of car rental companies.

But most of all, Boston is a charming and fun city to explore before you get deeper into the New England road trip itinerary.

If one thing to do in Boston is mandatory on the Northeast road trip, it’s the Freedom Trail. Walking the 2.5 miles (4 km) long trail, which presents top historic sites in the heart of Boston, is a one-of-a-kind activity.

After touring Boston, you don’t have to like baseball to enjoy a visit to Fenway Park. In all honesty, many visitors don’t even know the baseball rules when they enter Fenway Park for the first time.

However, baseball is an American tradition, and the Red Sox is the team in Boston. Catching a game and feeling the atmosphere at Fenway Park is a great experience before you venture further north on the New England road trip — baseball fan or not.

Where to stay

While there’s an array of charismatic Boston neighborhoods, keep in mind that the crowd-pleasing Freedom Trail runs from Boston Common, in the downtown area, to Bunker Hill, in Charlestown.

Cozy street with American flag in Beacon Hill, Boston
Beacon Hill, Boston.

2. Portland, ME – Traveling along the coast on the Northeast road trip

  • Driving distance: 112 mi / 180 km
  • Driving time: 2 h

Portland beautifully sits on Maine’s southern coast. This seaside New England city has a lot to offer for shoppers, foodies or just anyone who looks for a good time on the Northeast USA road trip.

The historic Old Port district — defined by cobblestone streets, red-brick buildings, quaint wharfs and fishing piers — is Portland’s crown jewel. As you wander around here, the facades remind you of past glory days.

But today the district is a modern-day gold mine with interesting boutiques, watering holes and restaurants. No matter if you want to shop, drink or eat, the Old Port, with a unique vibe, is the right place.

Capturing at least one of the many lighthouses in the Portland area is also a must on the ultimate New England road trip. And among all the proud beacons, there’s one that especially stands out.

Portland Head Light was completed in 1791 and is the oldest lighthouse in Maine. It’s known as the most photographed lighthouse in America — you surely don’t want to miss it on your Northeast USA journey.

Where to stay

Few disagree with us on this one: the Old Port is the best place to stay in Portland. However, your dollars last significantly longer elsewhere in Maine’s biggest city.

Portland Head Light on the Maine coast
Portland Head Light, ME.

3. Acadia National Park, ME – A spectacular park on the New England road trip itinerary

  • Driving distance: 172 mi / 277 km
  • Driving time: 3 h

It takes 3 hours by car from Portland to the only national park on the New England road trip itinerary, Acadia National Park. The best New England road trips include grand nature, and in Acadia you certainly find that.

Most of the national park is located on Mount Desert Island. Possessing some of the best parts of America’s wild Atlantic coastline, Acadia’s untamed attributes makes it one of the most beautiful places in the US.

You find awe-inspiring nature all over the island, but the eastern half of Mount Desert Island, home to a majority of the park’s most famous spots, is the by far most visited.

An unrivaled eastern highlight on the New England road trip itinerary is Cadillac Mountain. The views of Acadia National Park are just spectacular from Cadillac Mountain’s summit, the tallest point of both the park and USA’s eastern seaboard.

Cadillac Mountain is popular for sunrise and sunset but a beautiful experience at any time of the day.

On the quieter western half of Mount Desert Island, another photogenic New England road trip spot not to miss is Bass Harbor Head Lighthouse. Although not as old as Portland Head Light, this one was built in 1858, it’s one of the prettiest lighthouses in Maine.

The charming lighthouse is certainly a good reason to make the drive over to the less-traveled southern tip of Mount Desert Island.

View from Cadillac Mountain in Acadia National Park
View from Cadillac Mountain.

Where to stay

Bar Harbor is the most popular town with places to stay for Acadia National Park. From Bar Harbor, you have easy access to most of the highlights in Acadia National Park, including Cadillac Mountain, Sand Beach and the park’s loop road.

But if you’re interested in something off the beaten path, there are other options. Northeast Harbor is a smaller town that also sits on the eastern side of Mount Desert Island. And on the more quiet western side of Mount Desert Island, you find more options in Southwest Harbor.

Boats with American flags in Bar Harbor, ME
Bar Harbor waters, ME.

4. White Mountains / North Conway, NH – Driving into the White Mountains area

  • Driving distance: 209 mi / 336 km
  • Driving time: 4 h

New Hampshire‘s White Mountains is a region stuffed with great things to do on a Northeast US road trip. In the White Mountains area, you find both stunning natural beauty and cozy towns to relax in.

A shining example, North Conway is the perfect White Mountains gateway when you travel from the east. From the town, you effortlessly reach many highlights in the dense White Mountain National Forest.

Only a few miles away, Diana’s Baths Cascade — a series of waterwalls dropping 75 feet (23 m) — is a spellbinding place. Visiting is rewarding both for adults and younger travelers on a New England family road trip.

Another delightful road trip stop close by is Cathedral Ledge Lookout. From the vista, you enjoy spectacular White Mountains views — this stunning perspective makes a visit worth every step needed to get there.

When traveling further west, you unlock even more of the White Mountain National Forest.

Driving the famous Kancamagus Highway, one of the most scenic drives in New England, is a jaw-dropping experience. As it runs from Conway to Lincoln, it also, conveniently so, takes you right to your next base on the ultimate New England road trip itinerary.

Where to stay

Beware: North Conway’s charm may convince you to move there. Stay in the delightful heart of North Conway for maximum convenience, or go for its outskirts if you rather surround yourself with nature.

Spectacular lookout in White Mountain National Forest
Cathedral Ledge, NH.

5. White Mountains / Lincoln, NH – More fun in the White Mountains on the New England road trip itinerary

  • Driving distance: 42 mi / 68 km
  • Driving time: 1 h

At the end of the scenic Kancamagus Highway, Lincoln is a practical White Mountains gateway for highlights in the western part of White Mountain National Forest. Are you ready for more gorgeous terrain?

The Flume — a natural gorge offering a scenic pool, stunning waterfalls and, of course, mesmerizing White Mountain views — was discovered in 1808 by the lady Jess Guernsey. She came upon it by accident while fishing in the Lincoln area.

After the finding, as the story goes, Jess at first had trouble convincing her family about the discovery. It just sounded too magical to be true, but the rest is history. The Flume is a remarkable spot on the New England road trip.

However, hidden in Franconia Notch State Park, right outside Lincoln, the Flume is just the beginning of your Lincoln adventure.

You find a good variety of hiking trails in Franconia, letting you explore the White Mountains further. Here dense forests, stunning lakes and majestic peaks contribute to that unique White Mountains scenery.

Where to stay

Peacefulness is everywhere around Lincoln. With the Flume Gorge within a 10-minute drive, the convenience is spot on too.

Fall folliage on New England road trip
Kancamagus Highway leading to Lincoln, NH.

6. Green Mountains / Stowe, VT – A charming and romantic New England road trip stop

  • Driving distance: 84 mi / 135 km
  • Driving time: 2 h

A charming Vermont village with a postcard-worthy downtown area, Stowe beautifully sits at the foot of the Green Mountains in Vermont. It’s a place often mentioned among the prettiest small towns in America

Just strolling down Main Street in Stowe is an easy but appreciated thing to do when visiting. It’s a small town, but thanks to its peaceful aura, a walk couldn’t be more rewarding.

When visiting Stove, you’re never far away from fresh air and beautiful views. Stowe Recreation Path is a celebrated way to explore Stowe and the village’s lovely surroundings.

Walk, run or bike the paved trail — just be prepared for that you will want to stop to take pictures.

Not in Stowe, but just a short drive away, you find the ice cream lover’s dream. In Waterbury the original Ben & Jerry’s ice cream factory is located. It’s a tasty stop no matter if you travel solo, as a couple or take a family New England road trip.

White church nestled among trees and mountains in Stowe.
Picturesque Stowe, VT.

Additional stop: A beloved additional stop on the Northeast USA road trip is Burlington, VT. Burlington, a fun city on the shore of Lake Champlain, offers a great contrast to the quaint mountain town Stowe. As it’s just 36 miles (58 km) between the two, you can easily include both on your ultimate New England road trip itinerary.

7. The Berkshires, MA – Culture and nature hand in hand

  • Driving distance: 188 mi / 303 km
  • Driving time: 3.5 h

In the western parts of Massachusetts and Connecticut, you find the Berkshires region. It’s an area as known and appreciated for its rich culture as for its lush rolling hills.

The artist Norman Rockwell, known as America’s favorite illustrator, called Stockbridge his home for 25 years. Here, housing hundreds of original works, the Norman Rockwell Museum honors and showcases his contributions.

Before Rockwell, the writer Edith Wharton lived in the Berkshires. The Mount Home, Wharton’s historic Lenox residence, is declared a National Historic Landmark. Explore expansive grounds and, of course, learn everything there’s to know about the life of Wharton.

These are cultural treasures, but don’t forget that it’s the mix of culture and nature that makes the Berkshires so great.

For hiking, a beautiful spot is October Mountain State Forest. At roughly 16,500 acres, it’s the largest state forest in Massachusetts — offering both easy and strenuous trails, there’s something for every mood.

Where to stay

Berkshire towns at the heart of it all, Lenox and Stockbridge are excellent bases for soaking up both human-made attractions and the great outdoors.

Trail in October Mountain State Forest
Hiking in October Mountain State Forest.

8. Mystic, CT – A peaceful coastal village on the road trip in Northeast USA

  • Driving distance: 126 mi / 203 km
  • Driving time: 2 h

On the Connecticut coast, the village Mystic peacefully sits. Embracing its proud history as a waterside community and center for shipbuilding, it’s a charming place to visit on the New England road trip.

Mystic Seaport Museum is one of the leading maritime museums in the US. The museum on the Mystic River banks preserves artifacts of America’s rich seafaring past.

Enjoy an impressive collection covering 19 acres, with four National Historic Landmark vessels as the biggest draws. This is a stop for the New England road trip itinerary that’s both educational and fun.

For authentic shopping, diverse restaurants and charming waterfront views — the compact Historic Downtown Mystic has got you covered. Especially note Mystic River Bascule Bridge, a still-in-use drawbridge, nowadays a rare sight.

The quiet Mystic River in Connecticut
Mystic River, CT.

Additional stop: An alternative to Mystic or an additional stop on the New England road trip is New Haven, CT. The home to the famous Yale University is also a fun seaside city to visit as you tour Northeast USA.

9. Newport, RI – Salty Rhode Island shores on the New England road trip

  • Driving distance: 48 mi / 77 km
  • Driving time: 1 h

The salty shores of Rhode Island is an essential ingredient on the New England road trip itinerary. Newport, on Aquidneck Island, is an old colonial city with attractions covering a wide spectrum of things to do.

Walking the renowned Newport Cliff Walk, 3.5 miles long, is a beautiful way to appreciate the Atlantic coast. Tracing Newport’s rocky coastline, it offers stunning natural scenery and the saltiest of air.

In addition, Newport Cliff Walk is framed by many of Newport’s historic mansions.

With ocean on one side and Newport mansions on the other, the trail is nothing less than glorious. And as the cliff walk is free, exploring it is a great thing to do on a New England road trip on a budget.

But for the full experience, take a Newport Mansion tour to see how America’s wealthiest and most influential families used to live. The Breakers stands out for its extreme luxury, but the Elms and Marble House are certainly also impressive mansions to tour.

Where to stay

Newport Harbor, home to restaurants and bars, is the area where you find most of the city’s liveliness. However, there are also more secluded options for where to stay when visiting Newport.

Newspaper on green mansion lawn in Newport, Rhode Island
Mansion tour in Rhode Island, RI.

10. Cape Cod, MA – The idyllic Massachusetts peninsula

  • Driving distance: 120 mi / 193 km
  • Driving time: 2.5 h

Cape Cod, also known as just the Cape, is a peninsula in Massachusetts. Separated from the mainland by the Cape Cod Canal since 1914, it’s an idyllic place with true New England charm.

Cape Cod Rail Trail, excellent for walking or biking, offers a healthy way to discover Cape Cod. This paved Cape Cod trail, extending for 25 miles (40 km) from South Yarmouth to Wellfleet, follows the 19th century rail lines that used to carry tourists to Cape Cod.

Today, it’s different times, but the Cape Cod Rail Trail makes it possible to explore much of the beautiful peninsula without using a car.

At trail’s end, the landscape of Cape Cod National Seashore takes over. Hang out on the seemingly-never ending beach, seals thrive in the waters here, or hike around marshes and ponds.

The finish every peninsula should have, Race Point Beach is located on the very northern tip of Cape Cod. A phenomenal beach with huge sand dunes, it certainly motivates a drive up there.

As a bonus, Race Point Beach is a terrific location for sunsets and a great spot on a romantic New England road trip.

Where to stay

Cape Cod consists of Outer Cape, Lower Cape, Mid Cape and Upper Cape — all charming places to stay in Cape Cod. The Upper Cape, home to Race Point Beach and Provincetown, is furthest by car from the mainland.

House at Race Point Beach during sunset.
Sunset at Race Point Beach, Cape Cod.

11. Boston, MA – Finishing the Northeast USA journey

  • Driving distance: 116 mi / 187 km
  • Driving time: 2.5 h

After an unforgettable New England road trip adventure packed with natural beauty, postcard-perfect towns and fine tradition, it’s time to round of the Northeast USA journey. The last leg is the drive back to where the adventure started, Boston. From Provincetown it’s 116 miles (187 miles) to Boston, but it’s shorter if you base yourself somewhere else in Cape Cod.

A seagull at entrance to beach in Cape Cod
Beach on the New England road trip.

New England itineraries with days

For the ultimate New England road trip itinerary, it’s recommended to allow at least 3 weeks. If you have less time, it’s a good idea to break up the New England itinerary to focus on your favorite parts.

Ultimate New England itinerary (3 weeks)

  • Day 1-3: Boston (2 nights)
  • Day 3-5: Portland (2 nights)
  • Day 5-8: Acadia NP (3 nights)
  • Day 8-10: North Conway (2 nights)
  • Day 10-12: Lincoln (2 nights)
  • Day 12-14: Stowe (2 nights)
  • Day 14-15: The Berkshires (1 night)
  • Day 15-16: Mystic (1 night)
  • Day 16-18: Newport (2 nights)
  • Day 18-21: Cape Cod (3 nights)

2 week New England road trip (Atlantic coast)

  • Day 1-2: Mystic (1 night)
  • Day 2-4: Newport (2 nights)
  • Day 4-7: Cape Cod (3 nights)
  • Day 7-9: Boston (2 nights)
  • Day 9-11: Portland (2 nights)
  • Day 11-14: Acadia NP (3 nights)

7 day New England road trip (Mountain trip)

  • Day 1-4: White Mountains (3 nights)
  • Day 4-6: Green Mountains (2 nights)
  • Day 6-7: The Berkshires (1 night)
White Mountains on New England fall road trip itinerary
White Mountains in fall colors.

Final words about the unforgettable New England road trip

This New England road trip itinerary is loaded with the best sights of Northeast USA. It’s not just a New England road trip, it’s THE New England road trip.

Between the pristine coastline and quaint mountains town, it feels impossible to pick a favorite. But that’s exactly why this New England road trip itinerary is so great — you don’t have to pick.

Northeast USA road trip FAQ

You find the answers to some frequently asked questions about the New England road trip below.

How long does it take to drive the New England road trip?

The ultimate New England road trip is 1217 miles (1959 km) long. Driving it takes about 23.5 hours, not including any stops along the way.

What states are on the New England road trip itinerary?

The Northeast USA road trip includes the six states Massachusetts, Maine, New Hampshire, Vermont, Connecticut and Rhode Island.

What is there to do on a New England road trip?

A New England road trip is as much about its jaw-dropping nature as about its charming towns and proud traditions. In New England, beautiful nature meets covered bridges and quintessential lighthouses.

Where should I stop on a road trip in New England?

The main stops included on the ultimate New England road trip are Boston, Portland, Acadia NP, White Mountains, Green Mountains, the Berkshires, Mystic, Newport and Cape Cod.

Additional New England road trip stops include Burlington, VT, and New Haven, CT.

How long do you need to visit New England?

For the ultimate New England road trip, it’s recommended to have at least 3 weeks. But you can break the itinerary up and take shorter New England road trips too. Or you can even put all your focus on one single destination and make it a New England weekend getaway.

How can I spend 7 days in New England?

With 7 days in New England, it’s as good idea to concentrate on a certain area of the region. A popular combination is Boston and Cape Cod. With that combo, you get to see both a lively city and New England’s timeless coastal environment.

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