Road tripping New England
New England charms visitors with some of the country’s most picturesque scenery, and fascinates history lovers with many of its cities home to countless historic sites and attractions. With so much to see and do in this northeast region that includes Massachusetts, Connecticut, Rhode Island, Maine, New Hampshire and Vermont, there’s little doubt that taking a self-drive tour of New England is the best way to experience some of the area’s most alluring places.
Boston, the largest city in New England, is actually fairly small, with a population of just a little over 655,000. It’s highly navigable, clean and home to an astonishing number of historical sites and many other interesting attractions. If you’ve always wanted to experience a baseball game, there are few better cities to cheer along with die-hard fans than at the iconic Fenway Park, situated in the heart of the city.
Be sure to take a walk on the 2.5-mile Freedom Trail, Boston’s most popular attraction. A red stripe marks the route which traverses through the most historic neighbourhoods in the city, including 16 important sites related to the Revolutionary War. Begin at Boston Common before following it through the historic North End, finishing along the Charlestown waterfront. Some of the highlights along the way include Paul Revere’s home and the Old State Museum which showcases impressive memorabilia, such as the vial of tea that was salvaged from the original Tea Party crowd. You’ll also see the Old North Church, the very place where Paul Revere delivered his famous warning: “The British are coming!” back in 1775, ultimately sparking the American Revolution.
Head to the open-air observation deck at the Custom House downtown to take in panoramic vistas of the city and the harbour from the 26th floor, and be sure to tour one of the city’s most interesting attractions, the USS Constitution, the world’s oldest still afloat commissioned warship. Other highlights in Boston include the Institute of Contemporary Art on the South Boston Waterfront and tours at Sam Adams Brewery.
Explore the best coastal towns in New England along the coast of Maine, including Kennebunkport. Many associate this beach town with Dock Square, renowned for its shopping and dining, colourful eateries like the legendary Mabel’s Lobster Claw Restaurant, but to explore the true highlights of this area, you’ll want to take a side trip along the backcountry roads. Look for the lobster traps that are piled high on Cape Porpoise, a tiny strip of sand at Goose Rocks Beach that’s known as one of the state’s best hidden treasures.
In the state’s largest city, Portland, you’ll have the opportunity to enjoy a quintessential Maine experience: a scenic lobster boat cruise. Trips leave from the Portland Harbor and allow passengers to step into the shoes of a Maine lobsterman while enjoying views of historic lighthouses and civil war forts along with marine life like seals. Beer enthusiasts will find a lot to love about Portland too, it has a long history of microbrewing, and a number of top-notch local institutions like Allagash, which offers one of America’s best brewery tours. For close encounters of the state’s wildlife, visit the Maine Wildlife Park about 30 minutes north of Portland in the town of Gray, where there are over 30 species, including black bear, moose, bald eagle, mountain lion, porcupine and more.
Bar Harbor is a haven for nature lovers, famous for its stunning rugged coast as well as being home to most of Acadia National Park. This quaint seaside town is exceptionally diverse, with everything from the sea to soaring mountains. Get out and stretch your legs on one of the many hiking trails, including one that leads to the summit of Cadillac Mountain where awe-inspiring views await, or paddle in a kayak or canoe along the Mount Desert Island coastline by joining a tour. If you’re here at the right time, typically around late September through mid-October, this is one of the best places in the entire country for autumn foliage, with jaw-dropping hues found along the 40-mile stretch of the Acadia Byway.
Venturing over to New Hampshire’s gorgeous mountain scenery, pay a visit to the town of Sugar Hill. Tucked within the White Mountains, it’s a popular retreat for romantic escapes and outdoor adventures, located near a number of ski centres. In the warmer months, you can hop onto the Cog Railway for a ride to the top of Mount Washington, New England’s highest peak, where you’ll discover some of the most spectacular views in the region. In town, the Sugar Hill Historical Museum hosts a sleigh that once belonged to actress Betty Davis, the “Grande Dame” of Hollywood’s Golden Age. In central New Hampshire’s Lakes Region, Squam Lake served as the setting for the popular film “On Golden Pond,” which is framed by lovely views of the White Mountain foothills and offers an idyllic place for a picnic.
For a scenic drive that includes views of covered bridges, colonial farmhouses and miles of forest, travel Route 112 between Conway and Lincoln before heading north to Vermont. This is rated one of the nation’s best drives for fall colours, if you’re here during mid- to late-autumn. Burlington, Vermont is another ideal stop for brew lovers, hosting the annual Vermont Brewers Festival in the summer and a high concentration of breweries, including Infinity, Magic Hat, and the Vermont Pub & Brewery. The shire town of Woodstock exudes Americana charm with its pretty covered bridge, old country farms, lovely parks, and restored Georgian, Federal and Greek Revival homes. Don’t miss sampling the delectable maple syrups and cheeses at Sugarbush Farm.
The Berkshires of Western Massachusetts are legendary for their outstanding leaf-peeping as well as antique shopping and excellent museums. Stockbridge, famous as the birthplace of Normal Rockwell, is a must-stop with its multiple cultural attractions, including the Norman Rockwell Museum. Here you can find out which area landmark inspired author Herman Melville to write Moby Dick as well as view an impressive collection of Rockwell’s original works, his study and personal memorabilia. Enjoy at stop at Bash-Bish Falls State Park in Mt. Washington, for to remarkable three-state views.
Before making your way to Newport, Rhode Island, it’s worth making a stop in Providence, named America’s Top City by Travel & Leisure in 2014. It’s a legitimate culinary capital offering boat-to-table seafood direct from local fishermen at a number of restaurants, along with numerous cultural attractions, including seven performing arts venues alone. Stray off the direct route a bit and venture over to the highly appealing coastal town of Mystic, Connecticut, home to one of the country’s largest maritime museums, with over 500 vessels, including the last remaining whale ship in the world. It also hosts an aquarium and grand Colonial period homes, as well as Mystic Pizza restaurant, which inspired the 1988 film of the same name starring Julia Roberts.
Newport is internationally renowned for its historic mansions, some of which look more like palaces, like The Breakers, the grandest of all. A symbol of the Vanderbilt family’s social and financial preeminence during turn-of-the-century America and a National Historic Landmark, its interior cover 65,000 square feet of indoor space, and it includes a 13-acre lawn that overlooks the Atlantic. The city is also known as the “Sailing Capital of the World,” and offers the chance to charter and enjoy views of Newport and its mansions from Narragansett Bay.
Crossing the Sagamore Bridge into Cape Cod, a crescent-shaped peninsula with miles and miles of unspoiled beaches and sand dunes, tidal ponds, lighthouses, art galleries, museums and more, you’ll connect with scenic Route 6A. This popular drive passes blue inlets with Cape Cod Bay on one side, and white picket-fenced houses on the other. It links many of the Cape’s highlights, with the 117-mile route stretching all the way to Provincetown on the tip where you’ll find pristine stretches of sand along the Cape Cod National Seashore. This colonial seaport is a good place for a break with its abundance of eateries, cafes, art galleries and unique shops as the well a wide range of activities on the seashore, including kayak tours, ranger-led walks, and more. Along the way, you’ll find lots of interesting stops as well, including five lighthouses that can be toured: the Cape Cod Light, the oldest and tallest on the Cape; Nobska Point; Chatham, Nauset, and Race Point. The town of Sandwich is home to the Heritage Museum and Gardens, a 100-acre public garden, and the Sandwich Antiques Center, one of the best place to shop for antiques on the Cape, if not the entire nation.
On your way back to Boston, take time to visit Plimouth Plantation, a living history museum, where you can experience the village of Plymouth just as it was in the 17th century.
If you’re not ready for this incredible self-drive to end just yet, consider adding on a trip to Niagara Falls, one of the world’s most famous waterfalls. Marking the U.S. and Canada border, over 750,000 gallons of water per second thunders down the 167-foot-high waterfall that’s considered to be the most powerful in North America.
More things to explore in New England
New England photos
Top 10 things to do in New England
Top 10 coastal towns in New England
Explore New England in the Fall
Top 10 things to do in Maine
A beginner's guide to Acadia National Park
Top 10 things to do in Boston
Cape Cod beach holidays
A beginner's guide to New Hampshire's White Mountains
Self-Drive Classic New England tour
New England Travel Guides
- Road tripping New England
- Top 10 things to do in New England
- Top 10 coastal towns in New England
- A beginner's guide to New England's fall colours
- Explore New England in the fall
- Top 10 things to do in Maine
- Top 10 things to do in New Hampshire
- Top 10 outdoor experiences in New Hampshire
- Maine beach holidays