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Best Hiking Trails in Greater Boston

Updated on January 29, 2015

What is hiking? If it is no more than walking, a person can simply step out of their office building in downtown Boston and go for a hike on the Freedom Trail, or down the recently opened Greenway. If, however, a hike must include trees and perhaps water - like a lake or stream - perhaps a stroll along the Charles, a walk along the Muddy River or a jog around Jamaica Pond might suffice. But if a hike means a couple of solid hours in natural surroundings to you, I recommend one or more of the following hiking venues.

Hammond Pond Reservation, Newton

Minutes from downtown Boston, this 114-acre wooded reservation offers hiking through rolling terrain. Day camps actually bring their campers here to practice rock climbing on the huge granite boulders. Work up an appetite on the trails and then drive 2 minutes to the Cheesecake Factory or Legal Seafoods on nearby Route 9.

There is a place where one of the trails crosses the D branch of the Green Line trolley. Be careful: some of the drivers slow down and some don't.

To get there, follow Beacon Street straight from the State House on Beacon Hill out past Boston College and take a left on Hammond Pond Parkway. The entrance is down about a mile on your left. There is no formal parking.

Cutler Park, Newton

Cutler Park, 800 acres

30 minutes from downtown Boston.

Trails wind through wetlands surrounding the upper Charles River and Kendrick Pond. Never far from Interstate 95, the constant sound of tires on asphalt seems incongruous while hiking these wooded paths. The park is home to hundreds of species of birds including great blue herons. On your way you will visit two islands, Powell Island and Pine Island. Terrain is flat, mostly paths through woods leading to water views, with occasional boardwalks and an underpass beneath the commuter rail railroad tracks.

Usually when we go there we canoe up the Charles. We put in at Nahanton Park across the river in Newton and canoe into Cutler Park.

Parking is on Kendrick Street in Needham Heights near PTC.

From downtown Boston, go Route 9 west to Route 128 south. Take exit 19A toward Newton, take your first right, go to the end, you'll have to go left, then right. You'll come to a light. That's Kendrick Street, and Cutler Park is right across the Street.

Click here for Cutler Park map

Wilson Mountain Reservation, Dedham

213 acres

30 minutes from downtown Boston.

Wilson Mountain Reservation is a patch of woods nestled between the Boston suburbs of Dedham and Needham, Massachusetts. Well-tended trails wind between huge granite boulders strewn among a mix of fir and hardwoods. A small stream trickles though the reservation from north to south. Trails are well-marked, but without a trail map we could not find the "panoramic views of Boston and the Blue Hills." Well, that means we will just have to go back sometime.

Off of Route 128/95, Exit 17, Route 135. Head towards Dedham. Parking lot 1/2 mile on right.


Click here for Google map

Moose Hill Wildlife Sanctuary, Sharon

2,000 Acres

30 minutes from downtown Boston.

Offering views excellent views of Gillette Stadium and the surrounding countryside from Bluff Trail, the sanctuary features easy to moderately easy hikes through hardwoods and wetlands. Bluff Hill is perhaps a 100-foot ascent. It is briefly steep and can be challenging in snow.

The Visitor Center features a nature art gallery and gift shop. (One chilly autumn day we went there and they had fresh baked chocolate chip cookies and hot chocolate, but it was only that one time.)

In spring they tap the maple trees and make maple syrup. Audubon Society staff offer presentations on the process.

Click here for Moose Hill web site

Click here for MapQuest directions from downtown Boston

Blue Hills Reservation, Milton

7,000 Acres

20 minutes from downtown Boston

One of the most popular nature spots in the Greater Boston Area.

Offering excellent views from the Skyline Trail and some moderately challenging terrain, this is a popular destination. Great Blue Hill offers a more than 200-foot ascent from base to summit. Take Interstate 93 South from Boston to Exit 2.

Blue Hills also offers skiing in winter and swimming at Houghton Pond in summer.

An added attraction is the Massachusetts Audubon Society's Trailside Museum located nearby at 1904 Canton Ave in Milton, MA. They treat injured wildlife there, and some of those animals that cannot be wholly rehabilitated are there on display, including a few hawks and perhaps an owl. The Audobon Society also has a gift shop there.

Click here for MapQuest directions

Broadmoor Wildlife Sanctuary, Natick

626 acres

40 minutes from downtown Boston

Nine miles of trails traverse a wide variety of terrain and vegetation, including wetland, hardwood forest, pine forest, open meadow, and an orchard. In winter, tracks testify that a large number of deer pass through the sanctuary. Hawks hunt the air overhead. The trails get hilly as they approach the Charles River and at the end of Glacial Hill Trail, but otherwise they are flat. All trails are easy to moderate. We have enjoyed them in all seasons.

Broadmoor web site

Driving directions from downtown Boston

Willard Brook State Forest, Townsend

2600 Acres

1 hour and 20 minutes from Downtown Boston

The best time to hike the trails here is before opening day in the spring when you can trek through the fragrant pine forests and overgrown farmland in peace and solitude. The park opens for the season on Memorial Day.

There are a couple of hills, none too challenging, but just steep enough to be interesting.

The park offers many recreational opportunities including swimming, camping and hunting.


Click here for Mapquest Directions

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    • soldonsunday profile image

      soldonsunday 

      7 years ago from Boston

      Thanks for the information, this is very helpful!

    • Tom Rubenoff profile imageAUTHOR

      Tom Rubenoff 

      9 years ago from United States

      Absolutely, Jessica. Hammond Pond Reservation is easily reachable by taking the number 60 bus out of Kenmore Square to the Chestnut Hill Mall. Hammond Pond Reservation is just north of the mall.

      You can find directions to Blue Hills Reservation on the reservation web site:

      http://www.mass.gov/dcr/parks/metroboston/blue.htm

    • JessicaR1211 profile image

      JessicaR1211 

      9 years ago from Boston, Massachusetts

      Can I catch any of these by the T or train system? Looks like some cool places to check out and get out of the city.

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