8 Ways to Explore Boston's Harbor Islands

Boston Harbor Beacon
Made Possible by
Curated by

Compared to the vast opportunity for adventure outside city limits, Boston Harbor Islands National and State Park is a jewel among land preservation efforts in the urban sprawl. With ample opportunity for walking, beachcombing, swimming, camping, kayaking, coastal paddling, sailing, and more, the park caters to a wide variety of outdoor enthusiasts that visit its islands each year. In fact, rangers estimate the annual visitor tally to be somewhere around half a million, more than 10 percent of the greater Boston area population.

And why wouldn't people visit? The area is fascinating. There are 34 total islands that make up the Boston Harbor Islands National Recreation Area. Some of these are tiny things, only suited for native wildlife. Some are larger and feature miles of hiking trails among coastal environments and manmade ruins. Brewster Island is home to the oldest lighthouse in the country, constructed in 1716. Georges Island is home to the preserved Fort Warren, once a prison for Confederate soldiers and designated as the first line of defense for Boston Harbor. Peddocks Island is an eerie place with abandoned ruins from World War I and II-era Fort Andrews, and it was actually the film site for Martin Scorsese's Shutter Island. 

Much like other natural reclamation projects, the Harbor Islands were not always as we know them now. In fact, many were either non-existent or unrecognizable to their current topography just a few hundred years ago. Long Island initially had a resort hotel and Spectacle Island was used for horse rendering (you don’t want to look up what that is) and then served as a landfill. Think about that the next time you summit the island’s highest point on North Drumlin; you’re standing tall on a compacted trash heap—but a pretty one at that.

Excepting Spectacle and Georges Islands, which remain open for another month, public ferry service to the Harbor Islands ends after Labor Day. So, if you haven’t made it yet, you just missed your chance—but here’s what you need to plan your to-do list for next year.

1. Kayaking

Circumnavigating Boston's Harbor Islands via sea kayak
Circumnavigating Boston's Harbor Islands via sea kayak Massachusetts Office of Travel and Tourism

Those new or old to kayaking can enjoy one of Spectacle Island’s hour-long kayaking tours. There are only 10 spots per tour, however, so these can book fast and you’ll want to arrive early to reserve a spot.

Though not recommended for beginner kayakers, it’s very possible to paddle out to, and paddle between, Harbor Islands. Due to the significant boat traffic, strong current, and sheer distance, putting in at Long Wharf is not advisable and should be attempted only by experienced sea kayakers who own gear for high visibility. Hull Gut, a narrow channel between Pemberton Point and Peddocks Island with strong cross-currents and significant boat traffic, is also dangerous, even for experienced sea kayakers.

Many kayakers prefer the launch site at Hingham Harbor Beach, the optimal launch time being an hour before or after high tide. Putting in at Hingham means a shorter paddle to Bumpkin and Grape Islands, two destinations beloved for their remote feel, wildlife, and wild berries. Regardless of your launch point, be wary of wind speed and marine forecasts—kayaking in the Harbor can be dangerous during poor weather conditions, but incredibly rewarding during mild conditions.

2. Yoga

The Boston skyline makes for a much better backdrop than the studio walls when you’re in downward dog, trust me. On Saturdays and Sundays during the summer, the park hosts two free, all-levels yoga classes — one on Spectacle Island at 10 a.m. and another on Grape Island at 11:30 a.m. Classes begin in July and end in September.

3. Sailing

From the ferry to Georges or Spectacle Island, you'll get a picture-perfect view of the city skyline.
From the ferry to Georges or Spectacle Island, you'll get a picture-perfect view of the city skyline. Eric Kilby

An obvious adventure sport available around the Harbor Islands is sailing. It may not be your sport, but sailing a private boat is the only way you’ll be able to reach the 21 Harbor Islands inaccessible via public ferry but open for public use.

Note that the park asks all boaters to anchor at one of the Boston Harbor Islands’ 30 public moorings. Some moorings are free, while others have daily usage fees. Reservations can be made online. All boats are allowed to “touch and go” at island piers, but priority access is granted to ferries. Georges, Spectacle, Peddocks, Bumpkin, Grape, and Lovells Islands all have dinghies available for public use.

4. Swimming

Officially allowed only in a lifeguarded area off the coast of Spectacle Island, swimming on the Harbor Islands has an understandable draw for many during the dog days of summer. Swimming is not technically permitted on other Harbor Islands, so swim at your own risk when you’re outside the protected area.

5. Hiking, Running, and Walking

Hiking on a bluebird day at Spectacle Island
Hiking on a bluebird day at Spectacle Island LilyyyB

It is because the Harbor Islands’ official website touts miles of hiking trails that I address the sport, if only to clarify that no, there isn’t really true hiking here. Trails for walking and running, yes — but not hiking. A few of the islands boast both paved and unpaved trails with little to no tree cover and are almost exclusively flat. The drumlins on Spectacle Island are the notable exception here, but even that “hike” nets you an elevation of 157 ft. Watch out Everest — we’re climbing you next.

If it’s walking trails you’re after, you’ll find plenty on the Harbor Islands. Special mention goes to Peddocks Island: it boasts the longest shoreline with trails through its interior in addition to those at its perimeter. For runners, Peddocks Island hosts a 5K race, and Spectacle Island and World’s End both have enough trails for trail and road runners alike to enjoy.

6. Camping

Beachside camping on Bumpkin Island
Beachside camping on Bumpkin Island sarahee

It’s no surprise that reservations fill up fast on the Harbor Islands; camping there is one of the area’s best attractions. From June to September, camping is available on Lovells, Grape, and Peddocks Islands, but Bumpkin Island seems to be the celebrated favorite. Often secluded, Bumpkin lacks the manmade structures, like Forts Warren and Andrews, that can detract from an island’s backcountry-feel. Bumpkin and Grape Islands grow wild berries in the summers and, along with Lovells, are home to natural wildlife, while Peddocks Island boasts its own bird and wildlife sanctuary at West Head.

To reach these islands from downtown Boston, you’ll need to transfer at Georges Island, and in some cases transfer again from your second destination. If you’re closer to Hingham, there are direct ferries that stop at Grape, Lovells, Bumpkin, and Peddocks Islands.

A word to the last-minute camper: sometimes reservations go unfulfilled. If your heart is set on camping at the Harbor Islands, I’ve known campers who show up sans reservations and haven’t encountered an issue. That said, I wouldn’t employ this strategy with a large group or if you didn’t bring your own tent. Also understand that if campgrounds reach capacity, you’ll be the first group to be turned away.

7. Fishing

Provided its not near boaters or swimmers, fishing is permitted on the Harbor Islands. You’ll need a fishing permit, and staff accepts MA, NH, RI, and CT permits. Among others, you’ll be able to hook bluefish, cod, striped bass, haddock, flounder, and skate.

8. Biking

With easy footing and harbor views, the trails on Spectacle Island are great for walking, running, or cycling.
With easy footing and harbor views, the trails on Spectacle Island are great for walking, running, or cycling. Laura Irwin

Unfortunately for cyclists and mountain bikers, the only Harbor Islands to permit cycling are World’s End, which is a peninsula in Hingham Harbor, and Deer Island, peninsula in Boston Harbor that houses the Deer Island Wastewater Treatment Plant. While Deer Island has only one 2.75 mile trail, at World’s End you’ll find a 4.5-mile network of trails used by both bikers and walkers. This coastal property is also suitable for cross-country skiing and horseback riding. Unlike other Harbor Islands, World’s End is open year round from 8 p.m. to sunset.

Do you recreate in a manner not covered here? Say, land kayaking, synchronized bird calling, or sit-down paddling? Call the Boston Harbor Islands rangers at 617-223-8666 to see if it’s a.) viable and b.) permitted.

Last Updated:

Next Up


Speaking with Award-Winning Photojournalist and Ultra-Runner Ben Gray


Silver Falls State Park in Winter: 3 Reasons Why You Should Visit Now