On the outskirts of the urban jungle of Boston lies a peninsula that, while still within city limits, seems worlds away. Visitors can take a scenic loop hike to Castle Island from Pleasure Bay Beach and back along a one-of-a-kind trail that can only be found in Massachusetts.

Pleasure Bay Beach is found along the shores of the enclosed Pleasure Bay. This is the starting point to the easy 2.2-mile Boston Harbor and Castle Island Loop Trail. You'll be led to Castle Island, which is home to the historic Fort Independence, then around the bay via a causeway until you end up back where you started.
Ethan Machemer/AllTrails
Along the trek, you'll pass a WWII memorial on your way to Castle Island. Now a peninsula, Castle Island was once an island but was connected to the mainland by a narrow strip of land back in 1928.
Dan R/AllTrails
Located on the 22-acre Castle Island, Fort Independence is a pentagonal fort built between 1834-1851. It was used by the military during WWI and WWII and is on the National Register of Historic Places.
Meghan M/AllTrails
The island is a beautiful place to stroll around, hang out, have a picnic, and watch the planes from Boston Logan passing by overhead.
Rebecca Melonakos

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Once you're done enjoying Fort Independence and Castle Island, continue the loop along the Head Island Causeway which circles around Pleasure Bay.
Meghan M/AllTrails
You'll find the causeway to be quite scenic with water on both sides and city views in the distance.
Brian Rossi/AllTrails
Eventually, you'll come back to where you started - at the beach! Feel free to grab your beach gear out of the car and spend some time on the sand and, if it's warm enough, go for a swim.
Kaleigh Hansen/AllTrails
If you're here later in the day, just know that the sunsets from this park are nothing short of spectacular.
Stephanie Potter/AllTrails

 

Have you ever walked to Castle Island on this loop trail? Let us know in the comments! For more information on the Boston Harbor and Castle Island loop trail, head to AllTrails.

For another fascinating loop trail, read our coverage on Charley’s Loop Trail located at Purgatory Chasm State Reservation in Sutton.

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