12 Must-Visit Islands in Massachusetts

When you think about U.S. island destinations, it’s usually the tropical ones that come to mind. However, while they are stunning, there are some magnificent islands off the coast of Massachusetts. They offer windswept beaches, captivating views, outdoor adventure, and centuries-old architecture. In an area notorious for its rich history, quaint towns, and authentic charm, Massachusetts’s enchanting beauty is the embodiment of these alluring islands out at sea. Here’s a preview of 12 must-visit islands in Massachusetts.

Now, read on to learn more about these fascinating islands and what they have to offer! You’ll notice that four of the islands are listed as Boston Harbor Islands. These are 34 islands and peninsulas that are part of a national and state park and can be reached in minutes from downtown Boston.

1. Nantucket

An island to tick off your bucket list is Nantucket, which was rated the best island in the world in 2016, so that’s saying something. Nantucket sits 30 miles off the coast of Cape Cod and features sandy beaches, incredible nightlife, quaint shops, incredible coastal dining, and plenty of outdoor fun. Explore the island’s lighthouses, buy a classic Nantucket basket, and search for nautical antiques. It’s an excellent place to relax and is loved by locals and visitors.

2. Martha’s Vineyard

Once you’ve been to Martha’s Vineyard, you won’t want to leave. This island boasts pristine sandy beaches, lighthouses, brightly painted gingerbread cottages, sailboats, farmer’s markets, celebrity sightings, and the magical horse carousel. So, it’s safe to say you will have a fantastic experience on the island. And the best thing is, it’s only a 45-minute ride on the ferry from Cape Cod.

3. Lovell’s Island, Boston Harbor Islands

Lovell’s island has a reputation of doom as it was the site of multiple shipwrecks during the 18^th and 19^th centuries. For example, in 1782, the Magnifique, a 74-gun French warship, sank off the coast of Lovells Island. Furthermore, a passenger ship ran aground during the freezing winter storm of 1786. Unfortunately, Sylvia Knapp and her fiance were onboard. There are rumors the unlucky couple were discovered clasping each other to keep themselves warm on the famous Lover’s Rock. However, despite its tragic history, the island is a popular destination for picnicking, swimming, and camping today.

4. Crowninshield Island, Marblehead

Visitors flock to Crowninshield Island to explore its sand beach, wooded hilltop, and small open field. This coastal island is located in the picturesque Marblehead Harbor. You can access Crowninshield Island by foot during low tide or by boat. This five-acre island offers an abundance of family-friendly experiences, like excellent picnic spots, a short-loop trail that offers breathtaking views of other small islands, the harbor, and 17^th-century Fort Sewall.

5. Cuttyhunk Island, Elizabeth Islands

Some consider this island the site of the first English settlement in New England. This is because, in 1602, colonists inhabited Cuttyhunk for a few weeks to harvest the island’s abundant sassafrass. Today, this 580-acre island features a magnificent coastline, the charming village of Cuttyhunk, incredible coastal wildlife, and the exclusive Cuttyhunk Club, a gentleman’s club founded in 1864. Cuttyhunk Island is part of the Elizabeth Islands, a chain of small islands extending southwest from the southern coast of Cape Cod.

6. Deer Island, Boston Harbor Islands

Deer Island is a popular spot for biking, boating, and hiking despite playing host to the Deer Island Waste Water Treatment Plant, which takes up most of the island. In fact, one of the best places to see the Boston Harbor Islands is from the southern tip of Deer Island.

7. Spectacle Island, Boston Harbor Islands

Spectacle Island is only four miles from downtown Boston and is technically part of the city. This stunning island has plenty of natural beauty and a rich history. However, it is one of Massachusetts’s newest recreation areas, as it only opened to the public in 2006. It features an incredible beach, several hiking trails, and a public marina. Getting to the island is easy: you can catch a ferry from Georges Island and Boston.

8. Chappaquiddick Island

Chappaquiddick Island is only occasionally a true island because bad weather usually separates this island from Martha’s Vineyard. For example, it was separated from 2007 to 2013. Furthermore, it is the perfect vacation spot for people who want to escape their stressful lives, but Martha’s Vineyard is too busy for them. Chappaquiddick Island has amazing scenery for hiking, cycling, and bird watching. Not to mention, its picturesque beaches are usually quiet and relaxing.

9. Monomoy Island

People visit Monomoy Island because of all the seals that laze on its shores. While the island was occupied by colonists in 1710, it was deserted by 1860 because of a blizzard that destroyed the harbor. But there is more to this island’s disastrous past. The island was inhabited again in 1876 when the Whitewash Village was officially established. However, many residents fled to the mainland because of a slew of violent serial murders and homicides occurred. As a result, there are no permanent residents on Monomoy Island today. Instead, it is a Federal Wildlife Refuge, making it the perfect place for gray seal sightings.

10. Grape Island, Boston Harbor Islands

This 54-acre island boasts stony beaches, winding woody trails, and many campsites. It is technically part of Weymouth and was the site of numerous small skirmishes between British forces and colonists. In fact, people have farmed on Grape Island for over 300 years. Getting to this island is as easy as catching a shuttle boat from the Georges Islands.

11. Castle Island, South Boston

If you want to experience the most incredible views of the Boston skyline, you must visit Castle Island in Massachusetts. This 22-acre public park is no longer a true island because, in 1928, it was connected to the mainland by a narrow causeway. This island houses Fort Independence, a stunning place to take a leisurely walk, picnic, or soak up the sun on Pleasure Bay.

12. Plum Island, Essex County

Plum Island has an 11-mile stretch of gorgeous sand beaches. It derives its name from the wild plum shrubs that grow on its shores. The island is divided into three areas: Rowley and Ipswich, Newburyport, and Newbury. You can access this island via a drawbridge or causeway. Plum Island sports historical sites, public beaches, and local businesses.

Summary of the 12 Must-Visit Islands in Massachusetts

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