To me, a road trip is the best way to explore the U.S. By driving the back roads and getting out of the cities, you really get to see the diversity and natural beauty of the country.
Having grown up on the north shore of Boston and gone to college in Manchester, New Hampshire, I’ve spent a lot of my life in New England. I’ve enjoyed many summers road-tripping up to the White Mountains of New Hampshire, exploring the Coastal Towns of Maine, discovering all the Charming Coastal Towns of Massachusetts, and visiting many of the Historic Towns of New England.
I may be a bit bias, but I think that New England is one of the most special areas in the country and the best region to enjoy a summer road trip. Covering roughly 71,000 square miles (most of which is Northern Maine), New England offers incredible natural beauty, delicious cuisine, friendly and welcoming people, and plenty of charm and history. It is comprised of six gorgeous states: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont – all tightly packed together and perfect for road-tripping.
Below is just one version of a New England road trip (this can obviously be altered in many ways depending on what you want to see and do). Though you’ll need at least 3-4 weeks to see it all, you can cover a lot in just a few days. Most people don’t have time to finish it all in one go, so consider breaking it up into separate trips.
Days 1-2: Boston, Massachusetts
Welcome to Bahstan: a ‘wicked awesome’ city that’s filled to the brim with history, sports culture, amazing food, a thriving theater scene, and harbor views around every corner of almost every street. This is a great starting point, not only because it’s the biggest city in New England, it’s extremely convenient to most places in the region. Highlights in Boston include the famous North End (home to incredible Italian food), quaint Beacon Hill, shopping on Newbury Street, strolling along the waterfront areas (the Charles Esplanade is especially beautiful!), and visiting the many museums.
A great way to see a lot of sights in a short time is to take a Boston Duck Tour. Learn about Boston’s long line of history as you stroll down the streets and float along the Charles River. “The Duck”, as they call it, is a World War II-style amphibious vehicle – it goes on land and water! The 80-minute tour takes you past landmarks like Boston Common, Faneuil Hall, and Quincy Market, before plunging into the Charles River to experience views of the Cambridge Skyline.
Day 3-4: North Shore (Massachusetts)
After exploring Boston, head north to the North Shore region of Massachusetts (my hometown area). Here you’ll find dozens of personality-packed cities and towns, wide beaches and intimate harbors, whale-watching cruises, excellent seafood, craft beer, and spectacular cultural attractions! A few towns in this area I highly recommend include Salem, Marblehead, Gloucester, Rockport, and Newburyport. All of these towns are pretty close to one another, and it would be easy to pick one to stay in and take afternoon trips to the others.
Day 5: Kennebunkport, Maine
Next up, head north to Maine. Make a stop at the beautiful coastal town of Kennebunkport, Maine. This tiny New England town consistently ranks as one of the top places to visit in Maine – it’s quirky, peaceful, and really charming! Stroll through the art galleries, enjoy a meal at one of the epicurean eateries, explore its rich colonial and ship-building past with a walking tour of Kennebunkport’s historic district, and take in the beautiful views of the rocky coastline.
Day 6-7: Portland, Maine
The seaport city of Portland, Maine, about a 35 minute drive from Kennebunkport, is a great place to spend a couple of nights. Between the picturesque harbors and wharfs, the eclectic mix of museums, delicious lobster, the robust brewery scene, nearby coastal parks and lighthouses, there is so much to fall in love with in Portland. The city is best known for its Old Port (the historic center of town, shown left) filled with quaint cobblestone streets and brick buildings, you’ll find a number of charming boutiques and art galleries, and plenty of eateries serving up traditional Maine-style seafood.
Day 8: Bangor Maine
Next, make your way 2 hours north to Bangor, Maine. Only 32,000 people call Bangor home, but it’s a charming little town in central Maine worth visiting for a day. It was once known as the Queen City of the East thanks to its prominence as a lumber port and location on the Penobscot River. Today it offers a charming little town feel in central Maine.
Take a stroll through Bangor’s downtown area. Here you’ll find several streets lined with boutiques, busy coffee shops, some excellent restaurant options, and a beautiful Waterfront Pavilion (known as the Bangor Waterfront). You can also see the famed author Stephen King’s house (he lives in Bangor).
Day 9-10: Bar Harbor & Acadia National Park, Maine
Head about an hour and a half to the coast to Bar Harbor, Maine, the main gateway to Acadia National Park (a highlight of this road trip), whose 50,000 acres is home to Cadillac Mountain. Acadia boasts rugged cliffs of granite along the coast and miles of forested trails, it is a true gem of Maine and the perfect place to get outside and explore nature.
Bar Harbor itself is a small town – home to only 5,500 residents year-round. However, the town hosts 2-3 million visitors annually, so there is plenty to do for visitors. Enjoy a waterfront walk, take in the natural beauty of your surroundings, learn about the fascinating history (throughout the Gilded Age, the wealthy and elite Americans used to holiday in Bar Harbor in droves), shop in the lovely boutiques, and, of course, indulge in all the wonderful places to eat!
Day 11-12: White Mountains National Park, New Hampshire
New Hampshire’s White Mountains are one of the most stunning regions of New England. With its rugged peaks, rocky gorges and notches, waterfalls, endless hiking trails, scenic drives, and mountain views all condensed into one area, this region is an underrated gem of the United States!
Some of the best day hikes up the mountain are Tuckerman Ravine Trail (4.2 miles, strenuous), Lion’s Head Trail (4.2 miles, strenuous), and Jewell Trail (5.2 miles, moderate).
You can stay in nearby Jackson, NH, a small resort town nestled in the heart of the White Mountain National Forest. It is known for its breathtaking views and is an ideal spot for a summer getaway.
Another excellent location to stay in the White Mountain area is Lincoln, NH, a great base to explore this area. It is a well-positioned resort town in the shadow of Loon Mountain Ski Resort and within the actual boundaries of White Mountain National Forest. This is a great spot for hikers, as the famous Appalachian Trail crosses through the northeast portion of Lincoln.
Day 13-14: Burlington, VT
Just around 3 – 4 hours west of the White Mountains (depending on what town you’re coming from) you’ll find yourself in Burlington: Vermont’s largest city. With a population of about 45,000 people, it feels more like a small town than a major city. Burlington is a fantastic town to explore for the day, it’s hip, artsy, and full of good, local food – think cheese, coffee, craft beer, maple syrup, and more! And, sitting on the shores of Lake Champlain, Burlington offers a lot for outdoor enthusiasts, so it’s great to come in the summer months.
Burlington is also home to the original Ben & Jerry’s Ice cream. If time allows, you can visit the nearby factory in Waterbury, VT, it’s one of Vermont’s most popular tourist attractions. During the summer months, crowds come to enjoy the 30-minute factory tours. Tours are first-come, first-served, and run about every 30 minutes from 9 am to 9 pm.
Day 16-17: The Berkshires, MA
Make your way south into The Berkshires, MA. This mountain range in western Massachusetts is dotted with charming towns. It’s a popular region for outdoor adventure with a ton of things to do in the summer months including various outdoor markets and concerts.
A great hike in the area is Mount Greylock: Located in the state park encompassing over 12,000 acres and standing 3,491 feet tall, Mt Greylock is the highest peak in Massachusetts. There are a number of trails that lead to the summit, and the views from the top are absolutely stunning! Towns in the Berkshires include: Alford, Becket, Dalton, Egremont, Great Barrington, Lee, Lenox, Monterey, Mount Washington, New Marlborough, Otis, Richmond, Sandisfield, Sheffield, Stockbridge, Tyringham, Washington, and West Stockbridge.
If you do overnight in the Berkshires, I recommend staying in the adorable town of Lenox, which is in the heart of the culture of The Berkshires. Here you’ll find antique shops, art galleries, and delightful art and music festivals during the summer.
Day 18: Back to Boston, MA
About a 2-hour drive east and you’ll be back in Boston. There are plenty of spots to stop along the way for more fun things to do.
Alternative Options: Cape Cod and Rhode Island
If you decide to extend your road trip to see more famous spots in New England, head south to Cape Cod, MA and Rhode Island. You’ll find more delightful towns and villages, picturesque lighthouses, yummy seafood shacks, and endless shorelines.
Make you’re way down to Newport, Rhode Island, only 1 hour and 30 minutes south of Boston. This town is best known for its iconic Gilded Age mansions. These stunning buildings were once the summer “cottages” of America’s rich and famous families – think glitz and glamour! Today, these mansions have been converted into museums where you can explore some of New England’s glitzier past. A great way to do this is by trolly, which includes The Breakers Mansion!
From here, it’s a little over an hour to Cape Cod, MA! A quintessential maritime region that has lured politicians and celebrities for more than a century. This Massachusetts coastal destination is truly worthy of its own vacation. This is also where you can catch a ferry to Nantucket or Martha’s Vineyard for a day trip or to stay a few nights.
