New England Road Trip | An Epic Journey Across Six States

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When you think of New England, what comes to mind? Do you picture the buzz of Boston, the region’s cultural hub? Or Massachusetts, its educational center? Perhaps your mouth starts watering as you imagine digging into fresh lobster dishes and creamy clam chowder in Maine.

The New England region is stunning, with a rich history, a gorgeous coastline, majestic green mountains, and lush landscapes. A trip to this northeastern part of America is your chance for fun-filled discovery.

Visit quaint villages and towns, make memories at popular city attractions, and learn about a significant chapter of the country’s colonial past.

All that and much more is possible when planning an adventurous road trip through the six New England states. This 10-day itinerary includes scenic stops in different cities. You’ll get suggestions that will make your journey a holiday to remember for months to come.

Best Time of the Year for a New England Road Trip

Summer takes first prize when holidaymakers plan their annual trips to this region. In New England, particularly, the summer months (June to August) guarantee bright, warm days. The temperatures are perfect for indulging in all kinds of outdoor activities.

However, like other destinations around the world, summer draws more crowds. If your vacay includes a long holiday weekend trip, expect many fellow travelers. The prices for accommodation, transport, tourist attractions, and food also tend to be higher.

But I’ll let you in on a secret: The ideal time for a road trip is fall (September to November). The New England fall foliage boasts vivid red, orange, yellow, brown, and gold hues. The colors alone inspire the most exquisite pictures. The mild weather conditions ensure successful outdoor adventures. Not to mention the bonus of reduced prices.

New England Road Trip Itinerary | 10 Days of Exhilarating Fun and Discovery

An area as diverse as New England is your exploration playground if you’re eager to notch up unforgettable road trip holiday experiences. This 10-day itinerary is the guide you need to uncover this treasured American region.

While you can’t cover the entire New England region in one trip, this itinerary shows you how to experience all six states. Massachusetts, Maine, New Hampshire, Vermont, Connecticut, and Rhode Island — are you ready?

Day 1: Boston, Massachusetts

Many New England road trip itineraries suggest Boston as your journey’s launching pad. It’s Massachusetts’ capital and the region’s cultural and historical beacon. It’s best to fly into New England via Boston Logan International Airport.

After you’ve picked up your rental car, your road trip itinerary starts with spending a full day exploring the “Cradle of Modern America.” First, make the most of a few free things to do in Boston.

To soak up the city’s history, you can discover Boston on the Freedom Trail. Wander along this 2.5-mile stretch, which covers 16 monumental American locations.

Highlights include the Paul Revere House and the Boston Massacre Site. If you’d like to take part in a guided walking tour of Freedom Trail, you can book a tour on Viator or book on Get Your Guide.

Beacon Hill is next on the agenda, one of the most visited neighborhoods in Boston. Here, you can meander through the cobblestone streets, appreciating the archaic architecture. Beacon Hill is home to the Massachusetts State House, the state capitol. It’s the Commonwealth of Massachusetts’ seat of government.

When in “Beantown,” you have to sample its most famous dishes. Grab a bite (a hearty breakfast and some cream pie are sure winners) at Café 26 downtown. While you’re there, go shopping for treats and trinkets at Quincy Market.

Where to Stay

The downtown area is a favored choice when travelers are looking for where to stay in Boston — the budget-friendly way. At nightfall, head to the Union Oyster House for a delectable seafood meal.

South End’s Revolution Hotel has chic modern rooms and bright urban stylings throughout the property. You’ll relish your first overnight stay here on this New England road trip.

The hotel’s complimentary bikes make a leisurely late afternoon cycle possible. Other facilities include a gym, guest lounge, bar, and restaurant. The city center is less than a mile away.

Day 2: Portland, Maine

Driving time from Boston to Portland (without Salem detour): 1 hour 43 minutes (112 miles)

Driving time from Boston to Salem to Portland: 2 hours (123 miles)

When embarking on a driving adventure, there are countless opportunities to meet new people, mingle with the locals, and make friends on the road. In Portland, you can do just that; Mainers are a friendly and welcoming bunch.

Before you leave, savor a scrumptious breakfast and travel snacks at the Boston Public Market. This might provide the energy you need to add a spontaneous detour to Salem, a little over half an hour away from Boston.

No prizes for guessing what the most prevailing attraction is in this charming town: the Salem Witch Museum.

To learn more about the events of 1692, visit the Salem Witch Trials Memorial — a meaningful Massachusetts landmark when tackling a New England tour. You can secure an admission ticket when you book a tour on Viator or book on Get Your Guide.

It’s finally time to head to Portland (a 1.5-hour drive from Salem if you choose the detour). Portland has thriving art and social scenes and many outdoor escapes.

Get your art appreciation on at the Portland Museum of Art. When it’s time for a refresher, a local craft brew at Allagash will hit the spot. The Old Port has many gourmet eateries where you can indulge in a tantalizing lunch.

Take a short 18-minute (8-mile) drive to Fort Williams Park in Cape Elizabeth to see the oldest lighthouse in Maine. The Portland Head Light is more than 200 years old and has its own gift shop and museum.

Also, if you’re into cars, you can drive 30 minutes south to the classic car museum in Arundel.

Where to Stay

To get a taste of the electric Portland vibe, spend the evening at Blyth & Burrows for amazing cocktails before turning in for the night.

La Quinta’s comfortable rooms are decorated with subtle tones and splashes of accent color. Enjoy the outdoor swimming pool and on-site fitness center if the mood for a quick workout strikes. You’ll feel well-rested and rejuvenated before you hit the road again as you continue exploring New England.

Day 3: Acadia National Park, Maine

Driving time from Portland to Acadia: 2 hours 50 minutes (170 miles)

So important is a visit to an American national park that it’s considered one of the essential things to do when touring parts of the USA. Naturally, all roads lead to Acadia National Park on this leg of your New England road trip.

At Acadia National Park, you can enjoy a quiet picnic or a day hike. If you’d rather have a quick sit-down meal, grab a light meal at the Jordan Pond House restaurant. You’ll enjoy marvelous vistas of the mountains and Jordan Pond while snacking on the restaurant’s pièce de résistance: their popovers.

Among the park’s star locations is Cadillac Mountain at 1530 feet (466 meters). You can walk along a scenic route and snap gorgeous pictures of the surrounding natural beauty. Travel along Park Loop Road, a 27-mile track connecting areas like Mount Desert Island, Jordan Pond, and Cadillac Mountain.

Bar Harbor is less than five minutes away from Acadia National Park. The town is an entryway to the hills, lakes, and coastlines of Acadia. You’ll be able to kick back and relax in this small town with its sublime ocean views, fresh seafood restaurants, and galleries.

Pro Tip: Cell phone reception, WiFi, and parking can be sparse at Acadia National Park. Ensure proper planning beforehand. This includes confirming all your travel arrangements and accommodation bookings so you don’t need to scramble at the last minute.

Where to Stay

Look no further than the small town of Bar Harbor — the gateway to Acadia National Park. Acadia Inn is cozy and comfortable, with a unique countryside atmosphere.

After a restful night in your spacious, well-appointed room, fuel up on the complimentary breakfast. The Inn has a swimming pool (with a hot tub) and direct trail access to the Park — just five minutes away.

Day 4: Gorham, New Hampshire

Driving time from Acadia National Park to Gorham: 3 hours 42 minutes (199 miles)

This is the longest stretch of your road trip and most enjoyable if you include cruising through the Kancamagus Highway on your way to White Mountain National Forest.

Explore the expansive White Mountains area and North Conway, less than 10 miles away. There are hiking trails, tourist attractions, water activities, and many scenic walks to enjoy.

The Conway Scenic Railroad is another major attraction. It’s worth keeping in mind if you’d like to experience a train ride around North Conway.

The Gorham Historical Society & Railroad Museum details the history of this region’s railway transportation system. Squeeze in a trip to the museum if you’re interested in seeing different locomotive models, railroad engines, freight cars, and more.

New England road trips are made extra special when they involve a wine tour. If time and your energy levels allow, or if you prefer one exclusive activity, a White Mountains Seven Birches Winery experience is calling. There, you’ll intimately go through the wine-making process with the winemakers themselves.

When it comes to dining in Gorham, you have a few outstanding options. For burgers and pizzas, Mr. Pizza Sports & Spirits and The Public House Eatery are your go-to spots.

If you know anything about Italian nonnas, they make no mistakes with the pots and pans — making Nonna’s Kitchen a fabulous choice for Italian fare. Yokohama serves yummy Japanese specialties for those with a more exotic palate.

Where to Stay

Gorham’s Top Notch Inn is an impressive lodging option with great prices. Travelers looking for convenient comforts and beneficial amenities (without breaking the bank) will appreciate their time here.

The property — located 16 minutes from White Mountain National Forest — features a heated pool, hot tub, restaurant, and bar. Stock up on road trip supplies before heading north to Waterbury in Vermont.

Day 5: Waterbury, Vermont

Driving time from Gorham to Waterbury: 2 hours 10 minutes (109 miles)

Drive further into northern New England from Gorham to Waterbury. You’ve now crossed over into Vermont, the capital of maple syrup and America’s number one producer of the sweet stuff.

Spend some time at Green Mountain National Forest for the wildlife appreciation portion of your New England road trip itinerary. The forest provides a natural abode for moose, bears, deer, beavers, coyotes, and many more animal species.

Because one of the most exciting highlights in Waterbury involves food and drink, make sure to swing by any (if not all) of these leading culinary joints.

First, you’ll need a filling meal to give you the zest you need for exploring. The oddly named Prohibition Pig is a restaurant and brewery in Waterbury well-known for its Southern-inspired offerings. 

Then, satisfy your sweet tooth at Ben & Jerry’s — an ice cream haven that also operates factory tours for those keen to get a behind-the-scenes look at the ice cream-making process.

For dinner, feast at The Deep End in Stowe — a 16-minute (10-mile) drive from Waterbury. This is a laid-back family restaurant specializing in pizzas and salads.

Fun Fact: When it comes to mysterious sea creatures, Vermont’s Lake Champlain goes toe to toe with Loch Ness. Some people who have spent time in Lake Champlain have reported sightings of the Champ — a dinosaur-like ‘monster’ lurking in these waters. Lake Champlain might be too far a stretch on this particular trip, as it’s almost two hours away. So it’s worth noting for a return New England trip.

Where to Stay

A true New England trip includes at least one opportunity to wake up to breathtaking mountain backdrops. At the Trapp Family Lodge in Stowe, mountainous beauty meets luxury living.

Enjoy homey accommodations in this Austria-inspired resort offering splendid views of Vermont’s rolling hills. On-site spoils at the Trapp Family Lodge include two swimming pools (both heated), a gym, a restaurant, and a bar.

Day 6: Lenox, Berkshire County, Massachusetts

Driving time from Waterbury to Lenox: 3 hours 18 minutes (219 miles)

The second lengthy part of this road trip is your journey from Waterbury to Lenox. As you drive into the Berkshires, you’ll see lovely green mountains. If you’re traveling between September and November, you’ll be dazzled by the fall foliage.

For summertime visitors, check which music shows are running at Tanglewood. Depending on your travel dates, you may be lucky enough to see the Boston Symphony Orchestra on their Lenox tour.

The Tom Fiorini Sculpture Yard makes for some intriguing window shopping. It’s an eccentric collection of all sorts of fantastical metal, wood, and hanging art. You’ll also find jewelry, furniture, and cheeky signs that are sure to inspire the inner artist in you.

To experience Berkshire County, head to North Adams, 28 miles from Lenox. Art buffs will want to make a quick stop at the Massachusetts Museum of Contemporary Art (MASS MoCA). The museum houses the most creative modern visual installations, exhibitions, and media arts.

Where oh where to wine and dine in Lenox? Why not take a culinary trip to different parts of the world during your New England tour? Alta Restaurant & Wine Bar has the most mouth-watering Mediterranean grub. If it’s French cuisine you fancy, Bistro Zinc in the historic downtown area won’t disappoint.

A really quirky, unusual, but enriching travel experience to try is YogaDance at the Kripalu Center for Yoga and Health in Stockbridge, 10 minutes away from Lenox. You might need a pick-me-up at this point of your New England road trip. So, this is the right place to revitalize before continuing on your journey.

Where to Stay

Another superb Wyndham offering is The Yankee, with its old-world, simple aesthetic. This property is in a wildlife sanctuary in the charming town of Lenox. You’ll love being in the heart of the Berkshires, surrounded by its bountiful magnificence. Property amenities include a gym, two swimming pools (one indoor), and a picnic area.

Day 7: New London, Connecticut

Driving time from Lenox to New London: 2 hours 6 minutes (129 miles)

The small town of New London, Connecticut, forms part of southern New England. It’s a beautiful seaside escape with a fascinating maritime history. Charming restaurants line the streets, and one of the most appealing landmarks is the city’s lighthouse.

First things first, make your way to New London’s waterfront district for good food and a little shopping. During summer, expect to find live music and entertainment from street performers.

Pop into the Noodles & Rice Bistro for a Thai meal, or get a slice of Italy at Tony D’s, a family-owned restaurant serving the tastiest plates of pasta in town.

Fort Trumbull State Park deserves a spot on your road trip itinerary for its divine views of the Thames River alone (yep, Connecticut has its own version). The Park also features a museum, a boardwalk, and a fishing pier.

Alternatively, go for a quiet walk along the picturesque pathways at Connecticut College Arboretum or visit the Lyman Allyn Art Museum. Here, you’ll find the creations of Louis Comfort Tiffany, the American stained glass master.

Hygienic Art Galleries in downtown New London are innovative spaces that’ll intrigue you. There’s also an art park where innovative presentations and performances are held.

Right around the corner from Hygienic Art Galleries, you’ll find the famous New London Mural Walk. Whip out your camera and take trend-worthy photographs along the 16 magnificent wall installations.

When it’s dinnertime, opt for the appetizing flavors of Caribbean dishes at Mambo Bar & Restaurant downtown (try their Chorizo Español Mofongo).

Where to Stay

The Holiday Inn offers no-fuss, no-frills accommodations in New London, an ideal resting place before you continue your road journey. There’s an on-site restaurant, a bar, an indoor pool, and a fitness center. You’ll get a good night’s rest in preparation for the next leg of your road trip itinerary as you move on to Newport.

Day 8: Newport, Rhode Island

Driving time from New London to Newport: 1 hour 1 minute (56 miles)

You’re nearing the end of your New England road trip, but there are still a few interesting activities in store for you. There’s no better way to get a snapshot of Newport’s natural beauty than to admire the coastline while cruising along Ocean Drive.

This journey will take about 20 minutes, and you’ll cover 10 miles of the most scenic route in Newport. After that, it’s on to some mansion tours. Witness the opulence enjoyed by the city’s wealthiest families during the so-called Gilded Age.

There are quite a few mansions to see, but the most remarkable are The Breakers, The Elms, and the Marble House. There is a highly recommended trolley tour that will take you to all these mansions and give you their interesting history and how they came to be.

By the time you’re done with your mansion tours, you might need a little fresh (salt) air.

This is a fitting segway to a trek along Cliff Walk, a 3.5-mile path that affords staggering ocean views. You don’t have to complete all five sections of the walk. Tackle an easy stroll along the first half from Memorial Boulevard to Ruggles Avenue. All road trips need moments of peace and serenity, and here’s your chance to get that.

If time is on your side, an afternoon boat cruise through Newport Harbor and Narragansett Bay will be an excellent way to wind down the day. You can book a tour on Viator.

Where to Stay

Wellington Resort sits right on the water in downtown Newport. The suites are super spacious, with all the amenities you need and serene views of the harbor. You have a fitness center and two swimming pools at your disposal.

This is the perfect accommodation for couples or a small traveling group (3-6 people) undertaking a New England road trip together.

Next Read: Rhode Island is loved for its beaches. If you’d ever like to explore the US’s best beach vacations, don’t forget to add RI’s Block Island to the mix.

Day 9: Cape Cod, Massachusetts

Driving time from Newport to Cape Cod: 1 hour 20 minutes (74 miles)

On the penultimate day of your epic New England road trip itinerary, you’ll be traveling to Cape Cod. Once there, make a major part of this leg in your journey about sun and sea.

How about a walk on a white sand beach, one of the best being Mayflower Beach in Dennis? It’s only 20 minutes away from central Cape Cod, and you can enjoy splashes in calm, tranquil waters. This is also a prime location to take in a one-of-a-kind sunset.

Cape Cod Bay is a striking region with unlimited natural beauty. Miles and miles of coastline provide travelers with a picture-perfect seaside retreat. You can spend a few hours exploring parts of the Cape Cod National Seashore.

In Sandwich, no more than 25 minutes (14 miles) away from Cape Cod, more sightseeing and holiday activities await. Attractions include the Sandwich Glass Museum and Shawme Lake.

For memorable dining options, Fishermen’s View Seafood Market & Restaurant in Sandwich is right up there. Mattakeese Wharf Seafood Restaurant in Barnstable is equally as impressive. They serve terrific Cape Cod lobster meals, and their steaks are pretty good too.

With a full belly and a day well spent in Cape Cod, keep extraordinary going with an old-school cinema experience at the Wellfleet Drive-In Theater. The venue is 50 minutes (34 miles) out from Cape Cod, but well worth it as a unique road trip itinerary item.

If you love the drive-in movie theater experience, here’s a list of drive in movie theaters in the US.

Where to Stay

Hyannis is one of the most convenient places to be when visiting Cape Cod. Hyannis Travel Inn is a good option if you’re looking for a simple, affordable overnight stay near Main Street. The decor has a classic, vintage feel to it and you get access to an indoor pool and a hot tub.

Next Read: Consider these stunning beaches in Gloucester for fun in the sun the next time you’re in Massachusetts.

Day 10: Back to Boston

Driving time from Cape Cod to Boston (without Plymouth detour): 1 hour 31 minutes (70 miles)

Driving time from Cape Cod to Plymouth to Boston: 1 hr 53 minutes (72 miles)

It has been a wild and wonderful week and a half, hasn’t it? And now, the journey has reached its conclusion. It’s time to head back to Boston, but you can still absorb some parting New England vibes before flying home.

As you wrap up your northeast road trip, leave Hyannis, where you shacked up for the night, and head to Sandwich. A flavorful breakfast is just what the travel doctor ordered, and the quirky Café Chew has all the food fuel you need.

Cranberry-Pecan Toast, Yogurt Parfait, Buttermilk Pancakes, Breakfast Sandwiches, and more — take your pick from a wide selection of eats. When you’re ready, get back onto the road to continue your voyage home.

A Plymouth detour from Cape Cod will only take you 40 minutes, making it possible to include one or two activities before heading to Boston. When the 1620 Mayflower Pilgrims left England, venturing to the ‘New World’, they arrived in Plymouth. That’s why this town holds a whole lot of history.

Keeping time in mind, consider visiting Plymouth Rock (the Mayflower Pilgrims’ arrival site), the Mayflower II (a recreated version of the ship), or the Plimoth Plantation. This recommended tour includes both the plantation and the Mayflower II.

Wine tasting or a wine tour would chip away at more time than is available for this last stretch of your road trip. But a quick stop at Plymouth Bay Winery for a souvenir bottle and a couple of jars of delightful wine jelly is a good idea. It’s a brilliant way to take a piece of New England back home with you.

Say cheers to Plymouth and drive to Boston (1 hour and 13 minutes), where you’ll drop off your rental car and prepare to fly to your home city.

Next Read: Are you a solo traveler who prefers braving trips to new destinations independently? Get tips for dealing with loneliness to ensure your holiday adventures never leave you feeling isolated.

To help you visualize this 10-day journey, here’s a map showing the location of all the mentioned highlights and stops.

New England Road Trip Itinerary | Tips for a Smooth Journey

The better prepared you are, the more enjoyable your road trip will be. Remember these five top tips to ensure your New England travels are worry-free from start to finish.

1. Road trip 101 is simple: pack accordingly (including how you organize your rental car). Even in summer and fall, the preferred seasons to travel here, you’ll need to cover your bases. To combat the breezy mornings and evenings, you’ll need enough sweaters. Other essentials to slip into your travel bag include long-sleeve tops, a rain jacket and umbrella (just in case), and comfortable walking shoes.

2. Cities like Boston and Portland get busy; after all, they’re the biggest cities in their respective states. As all road trips go, factor in varying driving times (e.g., make allowances for traffic) and try to be flexible. You’ll have a more rewarding expedition if you leave some room for spontaneity and on-road surprises.

3. For your overnight stays, aim to be based in or near each city’s downtown area. This is usually where you’ll find central accommodation, the best restaurants and shops, and a lively atmosphere.

4. If your budget allows, squeeze in a few curated experiences. These include food, boat, hiking, and walking tours. Decide on the kinds of activities you’d like to try and find affordable offers on trusted platforms like Viator and Get Your Guide.

5. Keep a New England road trip map on hand (digital versions are pretty nifty) to ensure you stay on route. You don’t want to risk getting lost or delayed due to a wrong turn. The highways can get tricky, but you’ll be just fine if you have reliable navigation tools at the ready.

Final Thoughts | New England Road Trip

There you have it: a 10-day New England itinerary packed with exciting activities and charming locations for your next road trip. Now that you have a better idea of where to go and what to do during your next road adventure, what’s left is for you to select your travel dates.

New England’s abundant beauty and tranquility are enough to spur a return trip. So, if your holiday bucket list sees you making your way back to the region, you’re covered. Check out the best places to visit in New England to ensure you don’t miss a single must-see attraction.