The Most Beautiful Islands in Massachusetts (2024)

When people think of Massachusetts, they generally think of New England, pilgrims, summer vacation, and fall foliage. The Bay State has all that, but it is also a great destination for getting the sand between your toes and the sea breeze in your hair in a true island experience. From the popular Boston Harbor Islands, home to a whopping 34 islands, to the barrier island, Plum Island, residents and tourists are spoiled with choice. These beautiful islands, dotted along its eastern shore, showcase the very best of Massachusetts with gorgeous scenery, stunning views, and historic sites.

Plum Island

Plum Island is a stunning barrier island located at the mouth of the Merrimack River where it joins the Gulf of Maine. Named for the plentiful beach plum shrubs that grow in the sand dunes, the 11-mile-long island is known for its beautiful white sandy beaches, incredible birdwatching, and the unspoiled beauty of the Parker River National Wildlife Refuge.

This 4,700-acre nature sanctuary is home to over 300 species of resident and migratory birds, including piping plovers who vacation on the island from April to late summer. The refuge contains several scenic boardwalks, a boat launch, a beach, and hiking trails. Plum Island is connected to the mainland via a bridge and has many attractions for sightseers, including the historic Plum Island Lighthouse on the northern end of the island, which was first lit in 1788.

Spectacle Island

One of Boston’s harbor islands, Spectacle Island, is easily accessible from the mainland via a public ferry that operates from May to October. Just four miles from downtown Boston, the island offers incredible views of the city, panoramic vistas of the harbor, and five miles of beautiful hiking trails. Spectacle Island has a fascinating history. It was inhabited by Indigenous people who used the land seasonally before European settlers arrived in the 1600s. Following a smallpox outbreak, the island was used as a quarantine hospital.

In the 1800s, the island was a tourist destination, then an industrial site before becoming a landfill. In the 1990s, reclamation efforts began to convert the waste dump into the beautiful park it is today. Opened in 2006, the island-turned-recreation area now has a gorgeous swimming beach, marina, and visitor center.

Thacher Island

A small island off the coast of Cape Ann, Thacher Island is split in two, with the Town of Rockport owning the southern end and the US Fish and Wildlife Service owning the north. The island’s best-known attractions are the 124-foot twin lighthouses that dominate its skyline. The only operating twin lighthouses in America, the lights were built by the British in 1771 and completed in 1861. The lighthouses are open to the public during the summer months — if you feel fit, you can climb the 156 steps to the top of the lighthouses and enjoy breathtaking views to the north and south.

There are also several scenic walking paths between the lights and around the island. Just a mile offshore from the town of Rockport, it is easy to visit Thacher Island. Boat or kayak over, or hop aboard the Thacher Launch, a small ferry service that operates on Wednesdays, Saturdays, and occasional Tuesdays from June through August. Reservations are required.

Misery Islands

Don’t be alarmed by the name, a day on the Misery Islands, comprising 83 acre Great Misery and 4 acre Little Misery, is anything but miserable. These stunning islands off the coast of Salem are jaw-droppingly beautiful, with blooming meadows, dramatic shorelines, incredible views, and historic ruins. They take their name from Captain Robert Moulton, who was briefly shipwrecked here during a storm in the 1620s. He described his short stay as "three miserable days."

Thankfully, the islands have gained a better reputation over the centuries and are now a popular destination for hikers, birdwatchers, and boaters. Visitors can enjoy over two miles of trails meandering through rare habitats. You can even walk from one island to the other if the tide is right; at low tide, Little Misery is accessible from Great Misery by wading through a narrow channel. The beach at Little Misery has an unexpected landmark, the remains of the steamship, The City of Rockland, which was wrecked off the coast in 1923.

Castle Island

Castle Island is a very special place. One of five peninsulas in Boston Harbor, the island is a 22-acre outcropping that was connected to the mainland in 1928. But that’s not what makes it special. The island is dominated by a huge military base, Fort Independence, which dates back to 1833 and replaced an earlier fortification built by the British.

Today, the entire island is a park and tourist attraction that is accessible via a concrete causeway. The fort and its beautifully landscaped grounds are open to the public year-round and contain over two miles of scenic walking trails.

Peddocks Island

One of the larger Boston Harbor islands, Peddocks Island, is a rural idyll with a few scattered homes, several historic sites, and lots of wildlife. Keep an eye out for some of the more unusual residents — wild turkeys and deer are known to roam the 210-acre island. Campers, birdwatchers, hikers, and history lovers will enjoy exploring Peddocks Island.

Check out Fort Andrews, built in the early 1900s and in use until 1946. Peddocks isn’t just a beautiful destination during the daytime. The island is at its best at night and holds regular "Park After Dark" events, a ranger-led evening of enjoying the incredible sunset, learning about the stars, and taking a night hike.

Chappaquiddick Island

Off the coast of Edgartown, Chappaquiddick Island is a rural retreat with just one road, a small store, and three conservation areas. The island is just a short trip from the mainland via public boat, which docks at Chappaquiddick Point, where you will find an idyllic white sand beach with breathtaking views across the water to Edgartown Harbor. The three conservation areas of Wasque, Mytoi, and Cape Poge are public to the public and packed with hiking trails that show off the best of the island, from its sandy shoreline and ocean views to the wooded hills towards the center.

Cape Poge is where you will find the Cape Poge Lighthouse, a classic New England light built in 1801. Mytoi is an entrancing and otherworldly 14-acre garden stocked with native and exotic plants and designed in the Japanese style to promote tranquility and harmony.

Making Memories on the Most Beautiful Massachusetts Islands

See shipwrecks from another era, climb the country’s only operating twin lighthouses, explore Civil War forts, and take a break in a carefully curated Japanese garden. There is so much to discover on Massachusetts’ beautiful islands. Take a day trip to spend a relaxing afternoon on the beach, swimming in the Atlantic Ocean, or plan a longer visit to cruise the Boston Harbor Islands, and learn a little of this region’s fascinating seafaring history, from ships charting a course to the new world to pirates hiding their booty in secret coves. Whatever your island vacation looks like, it is sure to contain some Massachusetts magic.