I’ve included a guide to the quaint and quintessential New England stops on a 10 day road trip below!
1 Day on the North Shore, Massachusetts
Massachusetts’s “North Shore” consists of the coastal towns North of Boston. Assuming you’re starting in Boston, head north to destination Salem. Salem has the history and intrigue to warrant a stop. Check out the Salem Witch Museum, meander through Pickering Wharf and browse the shops and tarot card readers on Essex Street.
From there, travel up another 30 minutes to Ipswich. Spend the afternoon exploring the beautiful Castle Hill on the Crane Estate and relax at one of the pristine local beaches. Just 20 minutes farther North is Newburyport. Stay at one of the adorable inns and enjoy dinner at this historic coastal town.
1 Day in Portsmouth, New Hampshire
Crossing the border into New Hampshire, Portsmouth is just half an hour north of Newburyport. The town is full of curated stores and local goods, quirky street art and historical homes. Check out the waterfront Prescott Park, which often has live music or movie nights.
Stop in Kennebunkport, Maine
On the morning of Day 3, drive 40-minutes up the coast to Kennebunkport. Kennebunkport has bright colorful buildings and a beautiful port. Stop here for breakfast and drive along Ocean Avenue to see the mansions and Bush compound on Walker’s Point.
2 Days in Portland, Maine
Continue on to Portland! Spend some time on the water and visit at least a couple breweries while in town. For a full itinerary click here!
Stop in the White Mountains, New Hampshire
On Day 5, it’s a 2-hour drive to the White Mountains on the Kancamagus Highway, considered one of the most scenic in the U.S. Part of the northern Appalachian Mountains, the White Mountains range from forests to majestic alpine peaks.
Stop at either Diana’s Baths or the Basin Cascade Trail, both beautiful waterfall walks. For a longer hike with mountain views Lonesome Lake Trail is a good bet. If opting for the full day excursion and experience, Mount Lafayette and Franconia Ridge is an exhausting but thoroughly rewarding hike.
Stay in Woodstock, Vermont
From Lincoln, the drive to Woodstock, Vermont is 1.5 hours. After a day of fresh air and exercise, a night at the Woodstock Inn is much deserved. This quaint village is “American’s Prettiest Town” and oozes charm. The area includes antiques shops, covered bridges and the Quechee Gorge.
Boston**
If you haven’t already spent time in Boston, this is when to do it! Add a couple days and check out these tips**
Stop in Providence, Rhode Island
It’s Day 6 and less than two hours south of Woodstock is the capital of Rhode Island: Providence. Park near Brown University and tour the area that includes: Benefit Street, the Providence Athenaeum, Thayer Street, and Prospect Terrace Park. On the way out of town, stop in the pleasant Federal Hill Neighborhood, home to the Italian immigrant community in the late 19th century, for a pasta feast and then dessert at Pastiche!
2 Days in Newport, Rhode Island
From Providence, it’s a 45-minute drive to Newport, Rhode Island. Here the focus should be on seeing the mansions (from both the inside and along the Cliff Walk) as well as spending time on the water. For a full itinerary, click here!
3 Days on Cape Cod, Massachusetts
And finally, finish with a 1.5-hour drive to Cape Cod. Biking, kayaking and exploring at least one lighthouse should be prioritized. Centrally located Woods Hole and Chatham both have the charm and convenience….and famous ice cream! Click here for a full itinerary or list of highlights.
For specific seasonal advice:
During the fall, consider stops at apple orchards and outdoor breweries along the drive! In the winter, Stowe and North Conway are beautiful. Check calendar listings for winter strolls and Christmas tree lightings. In the spring and summer, definitely take advantage of boating tours.
