Kayaking Boston Harbor. Photo by Robert Todd Felton.
caption Photo by Robert Todd Felton.
Paddling through the Boston Harbor Islands National Recreation Area

By Robert Todd Felton
AMC Outdoors, June 2010

Don't let the names fool you. For although the names that litter the map of Boston Harbor sound intimidating (try "The Graves," "Devil's Back," and "Roaring Bulls"), kayaking in the relatively protected and shallow waters off Beantown provides an enjoyable afternoon, or, if you time it right, a multi-day excursion including some of the finest camping within site of a major metropolitan city you will find. Having discovered the islands while working on a walking guide to Boston, I thought it would be a great idea to get to know them better from the vantage point of my kayak.

As with many good ideas that include camping and kayaking, the more I told people about my plan to explore Boston Harbor and camp on the islands, the more people were suddenly thinking up reasons I needed to bring them along. One friend, a forester, said he needed to investigate invasive plants on the islands. Another offered to come along just to help me with the finer points of my kayak technique. My buddy Kevin had the best reason; he just thought it was a great idea.


Boston Harbor Islands National Recreation Area comprises 34 islands, managed by a partnership of eight federal, state, municipal, and nonprofit agencies. Half of the islands, including the three with campsites, are managed by the Massachusetts Department of Conservation & Recreation. Visit their website for information on obtaining a camping permit. Please note that all the islands follow a carry in, carry out policy and most do not have access to fresh water. Before any trip, be sure to consult an accurate and detailed weather forecast and be sure to have a tide chart as well as a good pilot book or chart. Pets are not allowed on the islands. The biggest challenge may be in finding a good place to leave the car overnight, so the best case is to have a friend drop you off at Pleasure Bay, a protected inlet with good access to the harbor, but no overnight parking.

In the end, it was just me and Kevin, and our plan was relatively simple. Put in south of Boston at Pemberton Point, paddle the 1.8-mile stretch around George’s Island to Lovells Island to stow our gear and set up camp for the first night. After exploring the outer islands the next day, we would move camp another 4 miles across the water to Grape Island, in the calm Hull Bay. According to the ranger I spoke with at the Department of Conservation and Recreation (because it was after summer, I had to go through them rather than Reserve America to get camping permits), we would likely have Lovells Island to ourselves because the ferry season had ended. Because the 54-acre Grape island is one of the few without man-made structures and is a haven for all types of wildlife, especially birds, we might run across another camper or two, but not nearly enough to fill up the 10 individual campsites available on the island. We would camp there and explore the inner harbor islands, such as Sheep, Raccoon, and Hangman, before the easy paddle home. At least, that was the plan.

Snarled, standstill traffic on Route 2 into Boston forced us to switch gears and put in at Deer Island on the north side of the bay for a slightly longer paddle to Lovells, but that was okay with us. The tide was going out. Named for Captain William Lovell, an early settler of nearby Dorchester, the island has been the site of shipwrecks, a native American hunting and fishing ground, a home base for light keepers, and a military installation. Now, you can picnic on its grassy fields, swim off the beach, and stroll the massive fortifications that still remain. It is also one of the three harbor islands that allows for camping.

We landed on the northwest side of the island on a beach populated by hundreds of cormorants, squawking their complaints over our presence. Once the kayaks were secure, we crunched our way over thousands of blue mussel shells to explore the island. At the northern tip of Lovells are the remains of Battery Terrill, one of the many crumbling concrete fortifications on the island. You can duck out of the sunshine into deep dark underground caverns laced with tracks for moving artillery shells and other weaponry around, and then break out of the gloom to climb up on the ramparts. It was a crazy, surreal place, especially when contrasted with the south side of the island. Past the main part of Fort Standish, empty picnic tables, a yurt platform, a handful of empty buildings, and the well maintained ferry dock were signs of the busy and cheerful summer just passed.


About halfway up the shoreline of this 62-acre mix of abandoned military installations, poplar and spruce trees, shell-strewn beaches, salt marshes, dunes, and grassy fields was our campsite for the night—a lovely sandy spot facing Boston across the water. A campfire ring set out at the top of the rocky shore faced the city. Five artfully-arranged slabs of granite formed a ring of thrones around a fire pit. Knowing we had these chairs to relax in later, we quickly set up camp and pushed off for an afternoon paddle.

Our goal for the afternoon was to explore Little Brewster Island and "The Graves." Little Brewster is a 2-acre knuckle of rock that happens to be the country's oldest continually used lighthouse site. The original lighthouse on the island was bombed by the British on their way out of town in 1776 and rebuilt in 1783. Just to the north is a dangerous and infamous set of jagged rocks with a warning light on them, visible only at low tide, named The Graves. With the wind picking up and the surf breaking against the rocks, we opted to explore Little Brewster on foot rather than test the accuracy of The Graves' name.

After 45 minutes of easy paddling, the wind still at our backs and the tide receding, we reached Little Brewster. Though we were well past the season for lighthouse tours, we lucked out. On shore, we ran into Frank Colter, a Coast Guard Auxiliary volunteer who helps maintain the lighthouse. An excellent guide and salty storyteller, Colter explained that before the current shades on the tower were installed, when the great mirrors which focus the light's beam out to sea were positioned just so, the sun’s reflection would start little fires on neighboring islands. The flash of the current light can be seen 27 miles out to sea, he said.

However, it was one of the last things he told us that really caught our attention. Pointing to an incoming Coast Guard vessel, he said, "our shift ends tomorrow, but they are coming to get us today because of the gale blowing in tomorrow. Big storm brewing." Excuse me? "Yeah, 30 mile an hour winds with gusts up to 50. I wouldn't want to be out here." The last forecast we had checked before starting out had said rain, but nothing about wind. With that, we scurried back to our kayaks and paddled hard to Lovells with a worried eye on the high clouds. But soon we had our gear stowed for the night, a campfire crackling, and steaks sizzling on the grill. As we watched the last of the sun’s light play off the Hancock Tower and Prudential Center, we decided not to worry about the storm. How bad could it get? The lights of Boston flickered on and we watched the bustle of the city from afar. An evening party boat slowly chugged its way past us, the sounds of music and merriment adding to the surreal feeling of camping on a deserted island within sight of a major metropolitan area.

Sometime in the night, long after most of the city lights had winked out, the gale hit. By morning, lashing rains were pounding our tent and obliterating our view of Boston. We sat on our sleeping pads and debated the options. The storm was supposed to last through the day and into the next. We had plenty of food and a deck of cards, but even if we outlasted the storm, we'd have to go home once it cleared anyway. So we decided that if the weather broke, we’d make a dash for shore and swear to come back another day.

When the rain eased off slightly, we scrambled to break camp and tumbled into our kayaks for the nearly 3-mile paddle back to shore. Through rain and mist, and with a moderate wind pushing us along, we set our sights on the eerie 100-foot-high egg-shaped sludge digesters of Deer Island. As we rounded the point and paddled down the north side of the peninsula to land at Winthrop beach, the rain stopped and it became obvious that the gale was blowing over. By the time we stowed the kayaks on the car, the sun was shining. As we got into the car we started planning that next trip.