We Did the Research, This Is Officially the Strangest Hiking Trail Name in Massachusetts

There are so many wonderful hiking trails to explore in Massachusetts, all the way from the Cape Cod beaches to the Berkshire mountains. I love a good scenic route, but my favorite hikes are those that contain some type of historical element. Only In Massachusetts has previously told you about trails like Ford’s Folley, an abandoned Sudbury dam built by Henry Ford, and Dogtown, a creepy ghost town trail in Gloucester. There is also a historic trail near Beverly, Massachusetts, with one of the strangest names I have ever come across. Let me tell you all about the Misery Island Reservation Loop.

This unusual trail with a strange name is located on Great Misery Island, an 83-acre island within Salem Sound. The only way to get here is via boat. If you don’t own your own craft, no need to worry; you can easily book an Essex Heritage tour and motor over on their vessel, the "Naumkeag.” Trips leave from the Salem Ferry dock in Salem and take about three hours, allowing you approximately two hours to explore the island. Please note that reservations are required and that children under four are not permitted on these excursions.

With a name like misery, you might think that this is a backbreaking trail to conquer. However, the reservation loop is actually an easy 1.4-mile hike that can be completed in roughly half an hour. “Misery” refers to an unfortunate event that took place here centuries ago. 

It seems as though sometime in the 1620s, a perilous storm hit the area, and a local shipbuilder named Captain Robert Moulton became stranded out on the island while out harvesting wood. After being trapped for “three miserable days,” Moulton returned to the mainland to tell his tale. The group of islands where he rode out the storm was consequently named “Moulton’s Misery” and later changed to Great Misery (also known as Big Misery) and Little Misery.  

For many years, the island of Great Misery remained miserable. Then, in 1900, developers recognized its natural beauty and peaceful atmosphere, and everything changed. A posh resort named the “Misery Island Club” was built on the island, and wealthy vacationers from all over the area came to enjoy the resort’s luxurious amenities, which included a saltwater swimming pool, golf course, pier, and tennis court. Due to financial difficulties, the club was short-lived, and the island was later transformed into a local summer colony. However, in 1926, many of the community’s buildings were destroyed by a fire. Today, the Misery Islands are maintained by the Trustees of Reservations.

As you walk along the Reservation Loop trail, you can still see some deteriorating stone walls, an old staircase, and other resort ruins. And as you take in the quiet solitude and beautiful surroundings, you can clearly see why this spot was once chosen as a vacation retreat. The true beauty of the island still makes it a wonderful place to spend a leisurely afternoon in nature.

Have you visited the Misery Islands? If so, please tell us all about your trip. To book a trip to Great Misery on the Naumkeag boat, please visit the Essex Heritage website. To experience more island fun nearby, I suggest taking a trip to Bakers Island, where you can visit a historic lighthouse. Be sure to track your hike on the AllTrails+ app.