Island life is pretty rad. Beautiful beaches, sea breezes and incredible views are a given when you’re hanging out on any of these scenic and historic Massachusetts islands. While there are lots of beautiful seaside spots in this state, there’s something special about knowing that no matter what direction you travel, the beach will be there to meet you.
1. Plum Island, Essex County
Not to be confused with Plum Island Animal Disease Center, this barrier island is an 11-mile stretch of beautiful sandy beaches and wild beach plum shrubs. The island was featured on maps as early as Captain John Smith's rendering of New England. Today, Plum Island is divided into Newburyport, Newbury, Rowley and Ipswich. The area is accessible via a causeway and drawbridge. There are plenty of public beaches, local businesses and historical sites to explore. Check out beautiful Plum Island Beach for a great spot to picnic and admire the waves.
National Geographic ranked Nantucket as the best island in the world in 2016. So...that's pretty cool. Just 30 miles off the coast of Cape Cod, Nantucket is filled with quaint shops, sandy beaches, incredible coastal dining, vibrant nightlife and lots of outdoor fun. Roam the cobblestone streets, pick up a classic "Nantucket basket," explore the island's lighthouses and poke through nautical antiques. It's a lovely vacation spot that has been beloved by natives and visitors for years. Don't miss the springtime Daffodil Festival!
3. Castle Island, South Boston
Castle Island is a 22-acre public park that boasts incredible views of the Boston skyline. Though it is no longer a true island (it was connected to the mainland by a narrow causeway in 1928), Castle Island is home to Fort Independence and a beautiful spot to stroll, picnic and take in the beauty of Pleasure Bay. It is open to visitors year-round.
4. Martha's Vineyard
Known as Nantucket's big sister, Martha's Vineyard is the third largest island on the East Coast and a popular getaway destination for the wealthy and fashionable. Though the year-round population is only around 16,500 people, during the summer the population is known to balloon to over 100,000 people! Martha's Vineyard was also one of the earliest deaf communities in the country, and Martha's Vineyard Sign Language is a recognized and distinct signing language. Visitors to the island can look forward to beautiful beaches, quaint streets lined with taffy shops, clothing boutiques and old whaling manors. Don't miss the Flying Horses Carousel in Oak Bluffs – it's the oldest operating carousel in the nation. Ferries to the island run regularly from Hyannis harbor.
5. Grape Island, Boston Harbor Islands
Technically part of Weymouth, this 54-acre island features winding woody trails, stony beaches and plentiful campsites. Grape Island has been farmed for more than 300 years, and was the site of several small skirmishes between colonists and British forces. Grab the shuttle boat from Georges Island and explore this great spot for yourself.
6. Lovells Island, Boston Harbor Islands
This island may be beautiful, but it has a deadly reputation. Lovells Island was the location of multiple shipwrecks during the 18th and 19th centuries. A 74-gun French warship, Magnifique, went down off the coast of Lovells Island in 1782. In 1786, a passenger ship carrying a young Sylvia Knapp and her fiance ran aground during a freezing winter storm. Stories abound that the unfortunate couple were found clasping each other for warmth on what is now known as Lover's Rock. Today, the island is a popular spot for camping, picnicking and swimming.
7. Monomoy Island, Chatham
Seals. Seals, seals and more seals. That's what you'll find on Monomoy Island. Though the island was inhabited by colonists as early as 1710, Monomoy was abandoned in 1860 after a blizzard washed away the settlement's harbor. Whitewash Village was established in 1876, but a slew of violent homicides and serial murders led to many residents fleeing the island for the mainland. Today, Monomoy has no permanent residents and no paved roads, but is a designated Federal Wildlife Refuge and a great place to spot some beautiful gray seals.
8. Crowninshield Island, Marblehead
Also known by the far less interesting name of Brown Island, this isle is maintained by The Trustees of the Reservations. Though only five acres large, the island offers rocky shores, sandy beaches, meadows and salt marshes. You can actually reach this lovely island by foot during low tide, when the water recedes to expose mud flats.
9. Chappaquiddick Island
Though this small peninsula is only occasionally a true island – rough weather sometimes separates Chappaquiddick from Martha's Vineyard, with the most recent separation lasting from 2007 to 2013 – it's a great vacation spot for those who want to get away from the relative bustle of Martha's Vineyard. The island is full of great places for cycling, hiking and birding, not to mention some great, less touristy beaches.
10. Cuttyhunk Island, Elizabeth Islands
This island is sometimes considered the site of the first English settlement in New England. Colonists set up shop on Cuttyhunk for a few weeks in 1602, apparently to harvest the area's plentiful sassafrass. Today, the island's 580 acres boast stunning coastline, fascinating coastal wildlife, the charming village of Cuttyhunk and the notable Cuttyhunk Club, an exclusive gentlemen's club founded in 1864.
11. Spectacle Island, Boston Harbor Islands
Spectacle Island is technically part of the city of Boston. Located just four miles from downtown, this beautiful island has a rich history and lots of natural beauty. Opened to the public in 2006, this is one of the state's newest recreation areas and offers many hiking trails, a lovely beach and public marina. Ferries operate hourly to and from Boston and Georges Island.
12. Deer Island, Boston Harbor Islands
This island is home to the the Deer Island Waste Water Treatment Plant, which fills most of the island's area. Despite this, the area remains a very popular place for hiking, biking and boating. The southern tip of Deer Island is actually one of the best places to view the Boston Harbor Islands from land.
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