Pleasure Bay, Castle Island & Sullivan's

Having a few hours to kill we decided to make a circuit around Pleasure Bay, before returning our rental car to Alamo at Logan Airport.

Pleasure Bay can be found at the East end of South Boston, just across from the airport.

Sheltered by the Head Island Causeway the Bay is popular with local swimmers, sunbathers and sail boaters while the Causeway itself is utilized by anglers, walkers, runners and skaters.

The path around Pleasure Bay has been designated a Healthy Heart Trail by the Massachusetts Department of Conservation and Recreation and a full circuit is approximately 4K. (Incidentally I find that Boston is one of the best cities for walking and running).

 

Bear in mind though that apart from few short stretches on William J. Day Boulevard and around Fort Independence the trail is pretty much unsheltered and at times when the breeze isn’t blowing it can get quite hot.

At the North End of the trail, near to the paths up to the Fort, you’ll find Sullivan’s, a fast food joint and a South Boston staple since 1951. Sullivan’s offers the usual New England fare: Lobster Rolls, Fried Seafood and Ice Cream but the quality is good and the service outstanding.

Lines usually extend through the door but orders are taken quickly and efficiently at the three to four registers and the wait is surprisingly short.
 

The Clam Strips, Fried Shrimps, Chicken Strips and Crinkle Cut Fries were all good, not greasy and are served with single serve packets of Tartar Sauce upon request. The kids really liked the Vanilla Soft-Serve which can be ordered with fruit-flavored syrup swirled in. The Italian Soda was a bit too sweet for my taste but still good. (The best Italian Soda we had in Boston was the Torani Mango from the Cookie Monstah food truck on Chinatown Park, right next to the Paifang).
 

Meals can be eaten on the picnic tables out front (un-shaded) on the grassy hillside heading up to the Fort or on park benches in the shade. Since there were a lot of dog owners walking their pets on the same lawn the picnickers were using we opted for one of the benches.
 

A little way further is a clean and well-maintained playground where the kids can run around and blow off steam.  The area is not fenced off however and since some of the equipment is very large and impossible to see over or around my wife and I each sat at opposite ends of the playground so that at least one of us could have an eye on the kids at all times.

The rest of the trail swings around Fort Independence, where you can watch the boats cruise in and out of the Charles River Mouth on their way from or to open sea, and onto the Head Island Causeway which in parts is connected by a series of bridges.

Apart from the occasional rumble of jets taking off from Logan airport the walk around Pleasure Bay is a relaxing and invigorating experience.