To see New England in HD quality, make sure your Road Trip Planner includes the dates from mid-September to mid-October. Granted, New England is beautiful year-round, but unlike other regions, its busiest tourist season is during the Fall, where trees are blanketed in fiery colors and where you can walk through carpets of rust, orange, and yellow.
Indeed, the New England region is synonymous with Fall, so deeply entrenched is its connection to this season. But what many people overlook in their initial road trip planning is that this region is steeped in American History. Thus, a Fall Road Trip to New England not only gives you nature's colorful bounty but also a rewarding cultural experience. Add to that the abundance of festivals held during this season and the readily available succulent lobster and you have a pretty good thing going there!
So where do you start your road trip planning? For many of us, a New England Road Trip means flying first into Boston & then renting a car. This virtual road trip will take you in a clockwise loop over the course of 8 days where you’ll hit all six New England states: Massachusetts, Rhode Island, Connecticut, Vermont, New Hampshire, Maine.
Boston is one of the oldest cities in America with many things to do so plan on staying two nights here. For a hotel choice, I’d recommend choosing one with character like the B & B brownstone, Gryphon House. The following morning, if you’re a walker, hit the Freedom Trail! A good place to start is at Boston Common, the oldest park in America. This 2 ½ mile walk will take you past 16 significant historic sites. One site to explore more thoroughly is the Faneuil Hall Marketplace, where you’ll walk on cobblestone streets and meander in & out of shops, restaurants and historic buildings.
The next day, enjoy a scenic drive from Lexington to Concord and then south to Plymouth Rock. Here, your road trip planner should include explorations of Plymouth Rock, the Mayflower II, and the extraordinary Plimoth Plantation. There aren’t many places where you can catch a glimpse of living history such as the village found here.
Add Cape Cod to your road trip planner for your third night. Your best bet for a hotel during this busy season is in Hyannis because it’s the largest of the seven Cape Cod villages. Consider taking a ferry over to Martha’s Vineyard for the day if you’re interested in seeing the historic whaling town of Edgartown. Otherwise, Cape Cod has plenty to offer to fill a full day’s itinerary.
Heading into Rhode Island on Day 4 and if you’ve planned your road trip to start mid-October, then you should be able to catch Bowen's Wharf Seafood Festival. Here’s that lobster you were dreaming of… and clams… and well, it IS a seafood festival. Here you also have an option to enjoy a ferry ride from Newport to Providence if you’re interested in seeing sprawling estates set against color-laden backdrops.
From Newport, you’re only about 50 miles to Mystic, Connecticut for your overnight stay. For many visitors, this community becomes the highlight of their road trip because it’s a seafaring village dating back to the 1600s. Here you’ll find guides sharing “whale” stories, a 19th century tavern, a printing office, a lighthouse, and of course, boats. Consider adding a steamboat cruise along the Mystic River to your road trip planner. Even if you didn’t plan your road trip to catch Mystic’s Annual Chowderfest, I’m sure you’ll still find a tasty bowl of chowder somewhere in this historical seaport.
For the next two days, you will truly be hitting the road as you travel about 3 ½ hours to Woodstock, Vermont and the following day another 4 hours into North Conway, New Hampshire. Here’s where your thirst for Fall foliage will be slaked as you drive first through the Berkshire Mountains in Massachusets, then the Green Mountains in Vermont, through the acclaimed picturesque town of Woodstock and into the White Mountains of New Hampshire.
Pencil in Portland, Maine in your road trip planner for Day 7. You’ll emerge from the mountains and lakes to cruise along the rocky coastline, just in time to enjoy another lobster dinner before you last night’s stay in New England. The following morning, you have about a 1 ½ hour drive to Boston, so enjoy the Atlantic Ocean views while you can!
While some travelers like turning the wheel over to tour operators, others like to do their own Road Trip Planning so they can travel at their own pace and stop at whim. Either way, you'll get a memorable Fall Foliage Experience.