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Boston's Freedom Trail is a testament to how ingrained history is in the travel culture of New England, but history doesn't stop at Boston Harbor. From colonial history to the slightly macabre to an eccentric inventor who created a center of Medieval History, New England seemingly has all eras and genres covered. There's no shortage of history and can definitely make the travel and history enthusiast feel a little FOMO. So, how do you choose?


It's true that you could probably spend weeks on end traveling to historic sites across the Northeast. But to see the best-hidden gems of New England, sites that span some of the most interesting stories in American history, you'll just need three days, this itinerary, and a car to hit the road! Of course, you can adjust this itinerary to accommodate more days and more sites, but you won't want to miss the adventures waiting for you at these unique spots.

Related: 'Athens of America': How Boston Earned Its Historic Nickname

Day 1: The North Shore and Seaside New Hampshire

Starting out from Boston, head north toward the seaside town of Gloucester, Massachusetts. This is about a 1-1.5 hour drive depending on the traffic that will transport you out of bustling Boston into some of the most idyllic on-the-sea communities in New England. Located on Cape Ann, Gloucester is famous for its maritime culture complete with historic lighthouses, maritime art, and the tastiest lobster rolls a traveler could ask for. The real hidden gem in Gloucester, however, is an art deco medieval castle (two things that don't normally go together)...

Stop 1: Hammond Castle Museum

A medieval revival castle built by inventor John Hays Hammond in 1926, the building was his seaside home where he kept a private collection of artifacts spanning ancient Rome to the Renaissance. Visitors are transported back in time to a place more like Leeds Castle than coastal Massachusetts. You can take a number of tours, visit some stunning exhibits, and take some lovely photos.

  • Open: April-November (hours vary); Closed December-March
  • $20 for adults, $15 for senior citizens, $10 for children

From Hammond Castle, head further north, perhaps stopping a half-hour away in the cute, riverside town of Newburyport, Massachusetts for lunch. After lunch, keep making your way north until you reach the richly historical town of Portsmouth, NH.

Stop 2: The Moffatt-Ladd House

Among the shops and other historic houses in Portsmouth, New Hampshire, the Moffat-Ladd House stands out as a garden oasis that seeks to interpret the history of both free and enslaved people who lived there.

The house was built between 1760 and 1763 by John Moffatt, one of the wealthiest men in New England at the time. His descendants lived in the home for 150 years. It was also home to Prince Whipple, an enslaved man who petitioned the New Hampshire legislature for his freedom in 1779.

  • Open: June to October, 11 am-4 pm
  • $10 for adults, $8 for senior citizens, $3 for children

Related: Cottage Core Travel: A New England Guide to Historic Houses & Gardens

Day 2: Central New Hampshire & Vermont

Setting out from the coastal towns of New Hampshire (with a small detour to Kittery, Maine for breakfast if you feel so inclined to visit another state) head westward toward Manchester, New Hampshire. About 45 minutes away, this next stop is another historic house but with a bit of a modern twist.

Stop 3: Zimmerman House

For mid-century modern fans, Zimmerman House is one of the only Frank Lloyd Wright-designed buildings open to the public in New England. Operated by the Currier Museum of Art (which has accompanying programming about the famed architect), the house shook up Manchester's colonial landscape when built in 1949.

After Zimmerman House, make a journey a couple of hours to the west toward Vermont with a highly recommended lunch stop in Peterborough, New Hampshire. Ultimately, you'll be headed to Brattleboro, Vermont.

Stop 4: Retreat Farm

Equal parts history and interactive nature center and farm, Retreat Farm is a great stop, especially if you have children. They have a variety of tours including a historic barn tour, a meadows tour that includes the historic cow tunnel, and a piggery tour--that features an ox. This spot also has some fantastic food trucks throughout the week so if you didn't take that pit stop ahead of time, it's a great place to indulge in some epic, Vermont-made gelato or a local beer.

  • Open every day, dawn to dusk; book tours ahead of time via email
  • The cost to visit the farm is free!

Day 3: Western & Central Massachusetts

From southern Vermont, head southwest toward the famed Berkshire Mountains. Known for its refreshing outdoor hikes and quirky art scene, the Berkshires has its fair share of offbeat historical oddities, especially this one in Stockbridge, Massachusetts.

Stop 5: The Sedgwick Pie

Probably not a pie that you would want to eat--you have been warned. The Sedgwick Pie is, in fact, an eccentrically arranged family burial plot that is the final resting place for the famous Sedgwick Family with Massachusetts Supreme Court judge, Theodore Sedgwick and his wife Pamela in the center. Lore has it that Judge Sedgwick wanted the family buried in concentric circles so that when Judgement Day came and the family members arose, they would only have to see other Sedgwicks. That is a man who loves his family.

Also buried there is Elizabeth Freeman, also known as Mumbet, the first enslaved African American woman to successfully sue for her freedom in 1781. Her attorney in this suit was none other than Theodore Sedgwick.

Traditionally, modern descendants of the Sedgwick Family may still be buried there, which means there's a spot for American actress Kyra Sedgwick, should she want to be interred there, as well as her husband, Kevin Bacon.

  • Typically open mid-morning to early evening
  • The cost to visit the cemetery is free!

Heading back towards Boston, through Worcester, there is a seemingly sleepy, yet large reservoir surrounded by trees and roads that appear to disappear into the water...

Stop 6: Lost Towns in the Quabbin Reservoir

A series of small towns in the Swift River Valley of central Massachusetts was settled in the 18th-century colonial era. Two hundred years later, these towns were effectively ghost towns...underwater. In 1938, the Metropolitan District Water Supply Commission flooded these towns to create the Quabbin Reservoir for the eastern part of the state. Today, you can explore remnants of the town via trails that connect old foundations and abandoned roads. There are signs and historic markers along the way, so you can read up on the lives of Quabbin Reservoir's residents before it became the reservoir. If you'd like to take a quick fishing trip, the state's wildlife department regularly stocks the reservoir with salmon and trout too!

  • Open dawn to dusk
  • Free to walk the trails!