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6 New England Spots for the History Buff

Updated: Jul 3

New England is chock full of history. If you were to look up any town or city in the region, the date settled or incorporated could stretch all the way back to the 1600s:

Kittery, ME – 1623/1647. Dover, NH – 1623. Plymouth, MA – 1620. Westminster, VT – 1751. Providence, RI – 1636. Windsor, CT – 1633/1637.

Sure, you could visit any of these towns, but there might not be much to actually see or do, other than a brief stop on a day trip. So, which historical landmarks are “musts”? Let’s do a quick list with some details here:


Portland Head Light can be found in Cape Elizabeth. Construction began in 1787 per the request of George Washington and was completed in 1791. Its history saw the first congress, Alexander Hamilton as Secretary of State and the American Civil War. The nearby maritime museum once was the home of the lighthouse keeper.

Portland Head Light

New Hampshire

Portsmouth and Strawberry Banke. This area was first inhabited by two American Indian nations, then settled by Europeans in 1630. This harbor town’s west bank was settled first and is known as Strawberry Banke (home to wild strawberries), but the harbor served as a major point for trade. Paul Revere rode here in 1774 to warn the British Navy was coming to capture the port.

Tip: Visit the Strawberry Banke Museum to explore the history of the Puddle Dock area on this 10-acre living history campus.


The Freedom Trail will walk you 2.5 miles and visit 16 historical sites in Boston. It starts at Boston Common and winds through to the Bunker Hill Monument in Charlestown. Along the way you’ll stop at the State House, Old State House, Boston Massacre site, Paul Revere House, Old North Church, USS Constitution, and 10 others. Tours are available or a free map available and easy to follow.

USS Constitution, Old Ironsides


You’ll find the Shelburne Museum on 45 acres near Lake Champlain. Though founded in 1947, it’s home to 38 buildings, 25 of them with rich history (circa 1800s) and relocated to the museum grounds. It’s a place chock full of folk art and artifacts that span generations and has collections of great range.

Shelburne Museum


Mark Twain (born Samuel Longhorne Clemens) House and Museum are in Hartford. He lived in this gothic-style structure with his family, from 1874 to 1891. It was here where he wrote The Adventures of Tom Sawyer and Adventures of Huckleberry Finn, among others. Almost demolished in the 1920s, the property was saved and restored. Today, tours are available, though guided, and other special events are held throughout the year.

Mark Twain House and Museum

Rhode Island

Newport Mansions and Cliff Walk – The famous mansions of Newport are products of the 18th century to the Gilded Age and served as “summer cottages” for some of the nation’s wealthiest families. Though it dates as far back as 1663, the coastline bordering some of the mansions went undeveloped. It remained this way until the mansion owners started building paths that, when put together, now make up Cliff Walk. The Breakers (owned by the Vanderbilt family and most popular), Marble House (also a Vanderbilt property) and Salve Regina University can be found here.

The Breakers

Planning your own New England History Tour

Some of these, as you can see, feature multi-stops (like the Freedom Trail) and tours (Newport Mansions). Therefore, planning a visit can get quite intricate, overwhelming, or even frustrating!

Whether you are looking for a grand road trip or a luxurious cruise for your exploration into New England's historical gems, I encourage you to tap into the knowledge of your travel advisor at Milestones & Mondays for the best possible experience for your family.

Milestones & Mondays

At Milestones & Mondays Travel, I transform wanderlust into adventures & unforgettable experiences for active travelers looking to get away from the crowds and deeper into the destination with expedition cruises, small ship cruising, small group active vacations and solo travels for those seeking experiences beyond the ordinary.

When clients turn their travel planning over to me, they receive a custom itinerary for their trip based on their travel style, desires and budget as well as a trusted advocate in their corner. I help them navigate the vast options and challenges in planning trips that are off the beaten track, with unique and immersive experiences, and I am there to provide support as needed before, during and after travel.

Along with my premium travel planning services, many of my clients receive additional amenities and benefits when booking with me and my preferred luxury travel suppliers.

I invite you to browse my website and encourage you to subscribe to my email list to receive travel inspiration and the latest travel opportunities delivered to your inbox each week.

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