Enjoy the Outdoors at Castle Island

Most visitors, and possibly even locals, don’t know about this spot, so we’re introducing it to you: meet Castle Island.

Castle Island is a state park on a land-bound island surrounded by the Boston Harbor in South Boston. Castle island wasn’t always land bound though. Historically, the island was in fact an island, with a fort on it that was occupied by the British during the Revolutionary war until the Siege of Boston in 1775. A lot has changed since then, but there still is a fort. More on that below. Castle Island is the perfect destination to escape the city and be outside.

Getting to Castle Island:

• Castle Island is a leisurely 30 minute bike ride from The Upton. Guests can rent a Blue Bike (located one block from us on Tremont Street) and bike over

  • Blue Bikes is a public bike ride share program with bike stations throughout the city

  • Blue Bikes has a bike stand in Castle Island so you can drop your bike off and pick one back up when you are ready to leave

    • Picture of bike stand located at bottom of article

  • We recommend using Google Maps to find the bike route and avoid hills

• The drive takes 15 minutes and Castle Island has free parking

  • Anticipate weekends to be busier with more limited parking available

Food tip:

If you plan on staying awhile, one note is that there is only one restaurant located in the immediate vicinity. The restaurant name is Sullivan’s Castle Island and they offer a selection of fresh seafood. Have a lobster roll by the water! Review the menu for Sullivan’s Castle Island and make sure that you like the options. If not, bring your own snacks or meal. Yelp users say, “don’t be discouraged by the line, it moves fast.”

Castle Island Activities:

1. Go to the beach

   On the route to Castle Island is a beachfront named Pleasure Bay. Yes, there is a beach in Boston! The beach has lifeguards during summer months and is a great place to kick back and relax or go in the water. Even during Fall and Spring when it is in the 50s or 60s degrees, people grab a blanket and hangout on the beach. You won’t even feel like you are in the city.

2. Visit Fort Independence

Castle Island is the oldest fortified military site in British North America (according to MassHiss) and is home to Fort Independence. Fort Independence is a fort that has been occupied by many fortifications. Fort Independence is the 8th generation of the forts built on Castle Island. According to the Massachusetts Department of Conservation and Recreation, the fort is, “a five-bastioned, granite fort built between 1834 and 1851.” Author Edgar Allen Poe served at Fort Independence when he was in the army. The Fort is not currently open for tours inside but it may be in the future. The greenery in front is also ideal for a picnic, sunbathing, or playing frisbee.

More history from MassHist below:

When the British evacuated Boston in 1776 they destroyed their fort on Castle Island, leaving behind only a pile of rubble. General George Washington appointed Colonel Richard Gridley, his chief engineer, to refortify Castle Island and Colonel Paul Revere commanded the forces stationed there. After the Revolution, Massachusetts state forces garrisoned Castle Island, and in 1785, the Commonwealth also used the island as a state prison. In 1798, the federal government took control of the fort, and three years later the War Department began reconstructing the fortifications. Once complete, Castle Island was renamed Fort Independence. Beginning in 1834, the reconstruction of the fort was performed under the direction of Colonel Sylvanus Thayer. Using over 172,687 linear feet of hammered granite, Colonel Thayer completed the construction of the current Fort Independence in 1851.

3. Go for a stroll, jog, or walk

Castle Island has a pedestrian walk path that goes all the way around it beginning at the entrance of Pleasure Bay. The walk has lovely views of the beach, Boston Harbor, Fort Independence, and more. The views are much different here than you will find in the South End neighborhood and the island is a worthy destination even if just for a walk. This is an excellent place to meet a friend for a walk or jog around.

Blue Bikes have a location at Castle Island. They are located between Pleasant Bay and Castle Island.

Enjoy!