UPDATED JUL 14, 2020
Hiking in Boston isn’t really a thing, but hiking near Boston is. And with plenty of spots to choose from, you’re bound to find the perfect place to get lost for the day. Happy trails!
If you want to tackle a summit trail in Stoddard, New Hampshire but aren’t up for trekking the tall peaks of the White Mountains, you’re in luck. The Pitcher Mountain Trail in Stoddard is one of the easiest summit hikes in New England. But just because it’s easy doesn’t mean there aren’t great vistas. The view from the top is gorgeous and a popular spot to watch the sun set. Less than two hours from Boston, Pitcher can be hiked year-round, but we recommend visiting when fall foliage is at its peak in late October.
In the winter, Bostonians flee the city and often head to Wachusett Mountain in Princeton for a day on the slopes. While we love a good ski day after a big snowstorm, we also love all that Wachusett has to offer in the other seasons. One of the best ways to enjoy the mountain, which is about an hour from the city, is to hike it. The 1.4-mile Harrington Trail is the perfect way to work up a sweat on the steady ascent.
A 640-acre state park located north of the city in Saugus and Wakefield, Breakheart Reservation offers a lot of options for outdoor activities. One of the best ways to enjoy Breakheart is on its many trails, which are great for hiking as well as mountain biking and cross-country skiing. Climb the reservation’s seven rocky hills for stunning views of Boston, southern New Hampshire, and central Massachusetts.
While Hopkinton may be most famous for its role as the starting point for the Boston Marathon, it’s also home to a pretty terrific state park. There are plenty of trails of all levels that will leave you feeling like you’ve traveled really far from the city without having to make a long drive. After you’re done hiking, go for a swim in the Hopkinton Reservoir or paddle its waters on a kayak.
Explore the 10 miles of trails at Ward Reservation in Andover to discover some truly unique spots. Hike the three hills—Shrub, Boston, and Holt—for sweeping views. You MUST see the “Solstice Stones” on top of Holt Hill, which mark the cardinal points of the compass as well as the points of the summer and winter solstices and points of the spring and autumn equinoxes. Afterwards, take the boardwalk to Pine Hole Pond over a quaking bog that’s teeming with special plant species, including insect-eating greenery.
Head north of Boston to Harold Parker State Forest for wooded trails, a cozy campground and the perfect freshwater place to swim. Harold Parker has a ton of hiking options in the forest, but the Yellow Diamond Hike is a classic route. The 6.3-mile trail is of moderate difficulty and takes you through woodlands and near Salem Pond, which offers tranquil views. Take a dip in Berry Pond after your hike to cool down!
One of the premier hiking destinations in Southern New Hampshire, Mount Monadnock is less than two hours from Boston. The trail to the top of the mountain can be steep and rocky at times, but the view from the summit will literally take your breath away (and not just because you're panting from the hike). This truly stunning hike is one that shouldn’t be missed.
This 7,000-acre park can be found just south of the city, making it an easy destination for a quick escape. There are dozens of hiking trails to choose from at Blue Hills that can suit any ability level. Climb up to Blue Hills Meteorological Observatory to take in incredible views of Boston. You can also take a dip in the nearby Houghton’s Pond to cool off.
At the Ipswich River Wildlife Sanctuary, you can catch a glimpse of unique glacial land formations, like drumlin and an eskers, which were created 15,000 years ago (we won't judge you if you google that). Trek the 12 miles of trails at the sanctuary through forests, meadows, and wetlands, or up to the observation tower. Don’t miss the boulders stacked to create arches and a rock grotto on the adventurous and aptly named Rockery Trail.
The scenery at Halibut Point State Park is classic, rocky New England coastline at its best. Many Bostonians take pride in the fact that their city is so full of history. However, the 440 million-year-old granite at Halibut puts colonial-era monuments to shame. Hike the trails at this Cape Ann recreation area for a glimpse into the region’s stone mining history and for stunning views of Crane Beach, Mount Agamenticus in Maine, and the Isles of Shoals off the coast of New Hampshire that you definitely won’t take for granite.
This 2,200-acre park sunk its roots north of Boston in Lynn and may be one of the area’s best kept secrets. Lynn Woods is paradise for anyone who loves outdoor recreation. Lynn Woods has 30 miles of trails just waiting to be explored. If it’s open, take the spiral stairs up Stone Tower for long-range views of the area.
Because it was formerly an estate, Maudslay State Park on the Merrimack River in Newburyport offers not only miles of terrific trails for hiking, but it has a a lot of unique features as well. Head to the park in May or June to catch the masses of azaleas and rhododendrons in bloom. Gardens from the 19th century mix with rolling meadows and towering pines to make the landscape at Maudsley extra special.
Head just north of Boston to the Middlesex Fells Reservation to hike the 2,575-acre state park that straddles several neighboring towns. There are more than 100 miles of trails across the reservation that are great for any ability level, making it the perfect place for a hike in the woods. Wander along the Skyline Trail, probably the Fells' most popular trek, and snap a selfie with Boston from Wright’s Tower.
This 17-mile recreation area offers dozens of trails from the short and simple to the longer and more strenuous. Noanet Woodlands in Dover features woodlands, wetlands, and an old mill site, all of which provide a scenic backdrop during your hike. No visit to these woodlands would be complete without trekking up Noanet Peak for a gorgeous glimpse of the Boston skyline.
Head to Medfield to hike the 6.5 miles of trails in Rocky Woods. This nearly 500-acre green space combines nature and history with its five ponds and former quarry site. The trails at Rocky Woods offer a lot of flexibility, so you can make your hike short and sweet or spend the whole day exploring this beautiful wooded area. Challenge yourself with a hike up Cedar Hill to see for miles around.
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