If Jerry Seinfeld visited Castle Island in Boston, he would probably say, “What’s the deal with that?” If you’re visiting or new to the area, the name might confuse you. You might think you need a whole day to get to this “island”. You might think you’ll be able to see an exciting castle. Neither is true. Although it is neither an island nor home to any castle, it is a highly recommended location for an urban wike, beautiful scenery, and great people-watching!
Castle Island is located in South Boston on William J Day Boulevard, near the M Street and Carson Beaches. In fact, it was indeed an island before a concrete causeway connected it to the mainland in 1928. Because it’s no longer an island, no need for a boat! You can drive or take the bus right there. If you can, park in the large lot near Fort Independence and Sullivan’s seafood and burger shack. There is additional parking along Pleasure Bay. I have visited Castle Island approximately 10 times and found easy parking 9 of those times. Be aware that beautiful summer weekend days are extremely busy and parking may be difficult to find.
The first thing you’ll notice is Sullivan’s, a seafood and burger shack. They serve up great fried seafood, hotdogs, lobster rolls, and ice cream cones. If exercise is not one of your wiking goals, you can grab an ice cream to enjoy along the way!
There are two loops: the Fort Independence loop and the Pleasure Bay loop. Both are completely accessible and stroller-friendly. Both are also mostly unshaded, so bring the perfect sunscreen, hat, and sunglasses! If you wike both loops, you’ll have traveled 2.68 miles. It is a great place to elevate your heart rate and get in a bit of exercise!
The Fort Independence loop takes you around the pentagonal fort, built between 1834 and 1851. Preceding this fort, another fort was erected in 1643 in the same location. You may be thinking, “Maybe it’s called Castle Island because of the fort kinda looks like a castle…?” Sorry, nope. The place was called “Castle Island” or “Castle William Island” even prior to the first fort.
When you loop around Fort Independence, which is open for tours on the weekends in the summer, you’ll get some good views of Boston Harbor and be able to watch the planes descend into Logan Airport. This is where my little family viewed the tall ships coming in during the opening parade this past year. So fun!
The second loop takes you around Pleasure Bay. This loop is almost two miles on its own, and it
takes you out over the water, from which you can take in views of the city skyline while feeling the breeze in your hair. Take a look at this map for an aerial view of the route. A large part of this loop is completely exposed to the weather—be prepared! There is a shade shelter partway through with some benches where you can rest if needed.
The Pleasure Bay loop will take you back to Sullivan’s, where you began. I recommend wiking both
loops and then spreading out a picnic blanket to enjoy a lunch from Sullivan’s while the children play at the playground. Restrooms are nearby, too! There are plenty of shady spots to relax and eat near the fort, and there are lots of picnic tables. We used my new waterproof blanket purchased from Amazon on Prime Day (best holiday!) when we visited last with our Hike It Baby Boston group.
If you have young children and like to get outdoors, I highly recommend Hike It Baby. You can sign up for a free 90 day trial on their website and then access listings of tons of weekly hikes all over the country. It’s a great way to get outside, explore, and be active while making new friends. You can get a taste of what they do before you sign up by following them on Instagram @hikeitbaby.
While your children enjoy the playground, you can engage in some really fun people watching! Castle Island is a bustling place, and families of all ages from all over the city love it! Visit just once, and you will know why they love it so much!
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What’s your favorite thing about Castle Island? The views, accessible trail, people-watching, history, Sullivan’s, or something else entirely?