6 Best Hikes in Boston’s Reservation System

Photo: Ryan Hutton / Mass DCR

Find solitude in the heart of Boston with these six hikes.

Greater Boston’s metropolitan park system is one of the world’s best-known networks of greenspace. It includes the famed Emerald Necklace, as well as a smattering of city and state parks. However, the city’s crowning achievement is its bigger swaths of urban greenspace—and the gems in that crown are its reservations. 

Boston’s reservations are sprawling patches of forest and field that together constitute several thousand acres of preserved land. First conceived of in 1893, the reservation system has a long history, marked with the fingerprints of some of the nation’s greatest city planners and landscape architects. (Of course, any account of these reserve lands would be incomplete without noting how their original inhabitants, the Massachusett and Pawtucket tribes, were forced from them before having a chance to propose their own management plans.) Today, the system consists of seven wooded reserves, three riverside reserves, and 10 ocean reserves. 

The Massachusetts Department of Conservation and Recreation manages these parks to preserve their natural character. That means you’ll find everything from freshwater marshes to flowering meadows to dense hardwood forest. Each park has its own personality, but they all have one thing in common: Once you’re in them, it’s easy to forget that you’re within Boston city limits at all.

Thanks to that dedicated management, the reservations provide critical habitat for birds and wildlife—and offer some of some of the city’s best hiking. Here are a few favorite trails that stand out most. 

Blue Blaze Trail (1.8 miles) 

Circumnavigate Wilson Mountain Reservation’s eponymous hilltop on this blue-blazed loop trail. The entire route covers just 200 feet of elevation gain, making it perfect for a pre-brunch stroll or family jaunt. To do it, park in the lot off Common Street and pick up the Blue Blaze Trail going counterclockwise. Keep an eye out for bushy rhododendrons (blooming May and June), white-tailed deer, and songbirds. (If you want to bag the actual summit, take the red-blazed spur trail to the top about halfway through the hike.) 

Photo: Ryan Hutton / Mass DCR

Breakheart Loop (4.1 miles) 

Two lakes, dense woods, and an extensive trail system make Breakheart Reservation one of the best places to immerse yourself in nature in North Boston. To get the full tour, park at the visitor center and pick up the Saugus River Trail going northeast. This will take you around the park perimeter going counterclockwise. When the Saugus River Trail ends at the reservation’s northeast corner, pick up the Ridge Trail, which circles around the Breakheart’s southern half, tagging several scenic vistas along the way. 

Lynn Woods Loop (5.0 miles)

Spanning 2,200 acres of ponds and forest, Lynn Woods Reservation is an expansive getaway just 30 minutes from downtown Boston. While it hosts more than 30 miles of trails, one particular favorite is the 5-mile loop that traces the shores of Walden and Breeds ponds. To do it, start at the main parking area on Pennybrook Road. Head northwest on Jackson’s Path, which picks its way around Breeds’s northern shore. From here, take the Comel Path until you hit Walden’s shoreside trail. This trail will dead-end into the wide, forested Pennybrook Road, which will carry you south back to your car.     

Middlesex Fells Skyline Trail (7.5 miles) 

One of Boston’s bigger reservations, Middlesex Fells encompasses 2,575 acres of woodlands and wetlands near Stoneham. Its natural beauty was recognized early on: Middlesex Fells Reservation was first established over 100 years ago, and it was designed by the same landscape architects who designed Central Park. One of the best ways to appreciate this reservation’s long roots is to take a lap through its western half. Try the Fells Skyline Trail, which conquers about 7.5 miles and more than 700 feet of elevation gain. 

Blue Heron Trail (8.8 miles) 

The aptly named Blue Heron Trail traces the perimeter of Cutler Park Reservation, a protected marshland teeming with herons, hawks, and other birds. This route tucks in and out of quiet forest and open meadow, giving you a full sampler of the reservation’s varied ecosystems. (Pro tip: Visit right around dawn to enjoy the morning light glinting off the Charles River.)   

Blue Hills Skyline Loop (9.0 miles) 

Hike the full length of Milton’s sprawling Blue Hills Reservation on one of Boston’s best wilderness hikes. To do it, start at the Skyline Trail parking area (just across the road from the police station), and pick up the rugged Skyline Trail going northeast. After about 4 miles, you’ll hang a left onto the Crags Footpath—take your time on one of the more pristine wooded trails in the reservation. You’ll hit a junction after about 0.9 miles. Turn left and angle south along a few different paths to get back to the Skyline Trail. Then retrace your steps back to your car.  

All articles are for general informational purposes.  Each individual’s needs, preferences, goals and abilities may vary.  Be sure to obtain all appropriate training, expert supervision and/or medical advice before engaging in strenuous or potentially hazardous activity.