Massachusetts' Tiny Duo Of Forested Islands Off Salem's Coast Offers Secret Tidal Trails And Cottage Ruins

No one wants a vacation or day trip associated with the word misery, but don't let the name fool you. The Misery Islands, located off the coast of Massachusetts in Salem Sound, are anything but miserable to visit. An easily accessible destination, Salem is about a 30 minute trip from Boston by both car and train, and while you can enjoy the quintessential New England charm of beautiful architecture and cobblestone streets during every season, once fall rolls around, this historic city is undoubtedly one of the most popular tourist destinations in the state – in 2024, Salem shattered previous records by welcoming over a million visitors during the month of October.

It's true that on the mainland you can enjoy countless activities focused on uncovering the secrets of Salem's famous witchcraft trials year-round, but while peak foliage and Halloween festivities seem ideal when it comes to experiencing the best of what Salem has to offer, summer on the North Shore offers a strong draw all its own. What many people don't know is that Witch City is just a boat ride away from 83 acres of rugged natural beauty on Great Misery Island, the larger of a relatively unknown and underrated duo of islands located between the harbors of Marblehead, an unsung coastal town brimming with rich maritime history, and Cape Ann's Manchester-by-the-Sea. And while Little Misery Island may be small at just 4 acres in size, it makes up for it with unique views of an old steamship wreck from the shores of its beach.

Read on to learn how to take the road (or water) less traveled over to the Misery Islands, and things to do once you've arrived, including traversing miles of beautiful trails and wading through the sea from one island to the other.

There is no regular boating service to either one of the Misery Islands, so the only way to explore these unknown gems is to sign up for a boat tour or make your own way there. Essex Heritage offers seasonal options in the summer every Saturday, and tickets cost $40 for adults and $25 for children. You'll enjoy a three hour round-trip excursion, including a half-hour boat ride to and from Great Misery, with two hours to explore once you get there. While the Trustees of Reservations, an organization responsible for maintaining the integrity of over 120 historic and scenic locations in Massachusetts, including the islands, doesn't offer any boat tours, it does recommend independent travel by dinghy, canoe, or kayak.

These islands weren't always so isolated. Purchased in 1900 by the Misery Island Syndicate, this land was the home of The Misery Island Club and boasted amenities including a pier, clubhouse, tennis court, saltwater pool, and even a nine-hole golf course, as well as a collection of guest cottages. Initially a landing spot for high society looking to attend local tournaments and regattas, the club's popularity was short-lived, and it began to experience financial issues after only one year of operation. A colony of over 25 summer cottages emerged in the wake of the business's failure, but a fire in 1926 decimated many of the residences.

While its local counterpart of a similar size, Baker's Island, boasts grand private homes and mansions, today Great Misery Island is uninhabited. Lacking roads or a town of any kind, the most you'll see are the ruins of the old casino on the north shore and some cottage ruins on the southwestern shore, including one once owned by three brothers with the foreboding name of Bleak House.

It doesn't matter if you choose to travel by official boating tour or paddle yourself right out to Great Misery Island from the surrounding shores of Salem or Beverly, Massachusetts — either way, there will be plenty of natural, undisturbed beauty to behold once you arrive. This special place boasts over two and a half miles of trails, by which you'll travel through open meadows, traverse rocky shorelines, and view ruins that date back to the early 1900s. You'll also find aspen groves and no shortage of scenic ocean vistas from a variety of overlooks. The Great Misery Island Loop is an easy trail that runs around the perimeter of the island and takes about 30 minutes to walk.

If you only plan to spend a short time on the islands, it's crucial to plan your trip during low tide, as it's possible to wade from Great Misery to Little Misery during this time. The much smaller island of the duo presents the opportunity to experience something truly unique –- what appears to be a long series of barnacle-covered driftwood pieces protruding from the sand is actually all that remains of the wreck of an old steamship. The SS City of Rockland wrecked on the Maine coast and ended up settling here, where you can view what's left of it today.

If you want to explore more of what nature has to offer on the North Shore, just a shoreline away, perched on Cape Ann's rocky edge, is a granite‑scarred Massachusetts coast of tidepools, trails, and ocean views.