The New England region is rich in history—and luckily, a lot of that history has been beautifully preserved. This 6-day tour, which begins and ends in Boston, visits a handful of sites where the past really seems to come alive.
Day 1: Gilded Age Newport
If you don’t hit traffic, you can cover the 75 or so miles between Boston and Newport in about 90 minutes. The city’s top attractions are the “cottages”—Newport-speak for “mansions”—that line Bellevue Avenue along the magnificent shore. Don’t attempt to tour more than two cottages in a day because you’ll want to leave time for exploring the picturesque waterfront area. Between the glorious scenery and the serendipitous shopping, Newport is a perfect place to while away an afternoon. Linger into the evening for a drink or dinner near the water.
Day 2: Maritime Mystic
It’ll take about an hour to drive along the coast to Mystic, Connecticut, where your destination is Mystic Seaport Museum, which recreates an early 19th-century waterfront full of tall-masted sailing ships, and whaling captains. After several hours at the Seaport, head north to Sturbridge, Massachusetts, about an hour and a half’s drive. 
Day 3: An 1830s Time Machine: Old Sturbridge Village

What was life like in a New England farming village in 1830? You’ll find out in detail by spending a day at this living history museum, full of authentic buildings, costumed interpreters, and craft demonstrations. The get back on the Mass Pike and follow it to the western end of Massachusetts to visit the Berkshires, your base for the next 2 nights.
Day 4: The Berkshires

Begin in the morning in Pittsfield at the Hancock Shaker Village, which will give you a fascinating glimpse into the practices of this radical Protestant sect. Have lunch in Great Barrington, then, swing by the Norman Rockwell Museum in Stockbridge to how the iconic 20th-century artist captured an American way of life that was vanishing even then. Try to schedule this trip to coincide with an evening concert by the Boston Symphony Orchestra at Tanglewood, in Lenox. Spread out a blanket, picnic on the lawn, and enjoy the scene, one of the hallmarks of summer in New England.
Day 5: Colonial Deerfield
Find a backroads route through the Berkshires to reach Old Deerfield, a perfectly preserved town of historic houses, some from as long ago as the 1600s. A walking tour of the town takes you into a handful of the houses, furnished in period detail. From here, you’ve got a 2-hour drive to Portsmouth; take Route 2 for more lovely scenery (unfortunately, the end of the drive is on heavily trafficked I-495). 
Day 6: Portsmouth
Portsmouth, New Hampshire, is a gem of historic architecture, maritime sights and sounds, and funky shops and cafes. It’s worth a trip just for Strawbery Banke, where the historic buildings are the displays. More than 40 restored buildings are set around 10 acres, Take a little time afterward to explore Portsmouth’s cobblestone downtown before driving back to Boston (the trip should take about an hour unless there’s traffic—but there’s always traffic). 

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.