10 of the Best Hikes In and Around Boston

It might seem strange to go for a walk in a cemetery, but there’s nothing morbid about this beautifully-landscaped garden that sits along the border of Cambridge and Watertown. Take a stroll down paths that bring you past a sphinx, along hidden ponds, and up the central hill where Washington Tower overlooks downtown Boston.

Keep in mind that running and dogs aren’t allowed at Mount Auburn Cemetery out of respect for the generations of New Englanders buried here (which include the founder of Christian Science, Mary Baker Eddy, and the abolitionist Charles Sumner). Afterward, explore Harvard Square (just a few minutes away by public transit) while indulging your sweet tooth on a chocolate tour.

This aptly-named reservation on a tip of land jutting into Boston Harbor has narrowly avoided being transformed into a housing development, a nuclear energy plant, and even the headquarters of the United Nations.

This means that visitors can still happily ramble along 4.5 miles (7.2 kilometers) of paths, all with magnificent views of Boston and the Harbor Islands, and get to know the area’s serene, wild beaches. Get more of Massachusetts’s iconic ocean—it’s the Bay State, after all—on a whale-watching catamaran tour.

Known as one of the most challenging hikes in the United States, Pemigewasset Loop features 31 miles (50 kilometers) of punishing terrain. The good news is that it’s easy to break up the hike into two or three days, covering nine different peaks in a reasonable time frame—as long as you bring along a tent and sleeping bag. Whichever option you choose, those who complete the loop can enjoy some of the best views in New England in an extremely remote landscape. Those who want the views without the hike can drive the route instead.

The tallest summit in Massachusetts, Greylock is located on the Appalachian Trail and has commanding views of the rest of the Berkshires. You can see three states from the summit, and during the summer, you can even stay on the very top of the peak itself at the rustic Bascom Lodge. After your hike, spend some time in the bohemian town of North Adams, where Mass MOCA, a former paper factory turned museum, features pioneering works of contemporary art.

This 7-mile (11-kilometer) trail encircles the entire western half of the Middlesex Fells Reservation just north of Boston. Walk through open fields, cross wooded glens, and scramble up rocky hills to enjoy excellent views of downtown Boston. The reservation, also a popular spot for trail running, is open to dogs. Plus, the evocatively named Panther Cave is a short detour, as is Bellevue Pond, where you can spot local kids playing ice hockey in the winter.

Newport, home to some of the wealthiest families of the Gilded Age, remains a summer playground of the rich and famous. Although most people will never live in huge, historic mansions like The Breakers, anyone can enjoy the peaceful Cliff Walk that brings vacationers along 3.5 miles (5.5 kilometers) of paved trail right on the ocean’s edge. The walk is free and open to the public, offering stunning ocean views of Newport's eastern shore and beyond.

Related: Historic Mansions of Newport

The people who have occupied the remote Dune Shacks for decades (built out of the wreckage of ships that crashed near Cape Cod) know the meaning of living off the grid. Though it’s located in Provincetown, home to countless summer revelers and known as an international gay mecca, this far-flung trail and accompanying beaches feel far away from the rest of the world.

Park on the side of Route 6 and hike just over a mile toward the ocean before weaving your way in between the shacks. Poets, hermits, and travelers have all lived in these shacks, and some still do. The farther you get from the trailhead, the fewer people you’ll encounter on this unique journey.

Channel your inner Henry David Thoreau at Mass Audubon’s nature reserve north of Boston. With 12 miles (19 kilometers) of easy trails and a marsh landscape filled with countless bird species and other animals, this location is ideal for campers and canoeists. Launch your boat in the Ipswich River and paddle over to Perkins Island, where, on Saturdays, you can rent a campsite that feels decidedly remote. Afterward, don’t miss a trip to nearby Salem to learn the history of the witch trials before returning to Boston on a high-speed ferry.

The farthest corner of Massachusetts is home to the state’s highest waterfall, Bish Bash Falls, framed by a dramatic boulder that hovers 80 feet (24 meters) above an inviting swimming pool. Go for a swim after the short hike, which starts near the parking lot. Or, if you prefer to stay dry, hike up Monument Mountain instead, a favorite walk of writers such as Herman Melville and Nathaniel Hawthorne. Either way, end your visit to the Berkshires with a drive into the cozy town of Great Barrington to pop into art galleries and have lunch.

An iconic New England route, this 272-mile (438-kilometer) hike through the entire state of Vermont served as the inspiration for the Appalachian Trail. Hikers can choose to traverse any of its awe-inspiring sections without committing to doing the multi-week hike in one go. From Boston, take in highlights from the southern section, including Glastenbury and Stratton Mountains, before making your way back to civilization for a craft beer at the Long Trail Brewing Company in Bridgewater.