Hikes Near Boston

Midstate Trail, Central Massachusetts
A late but welcome discovery for me.  The Midstate Trail runs 95+ miles (reroutes add additional miles) north from New Hampshire across central Massachusetts to the south border with Rhode Island.  
Wachusett Mountain and Mount Watatic, the last undeveloped mountain east of the Connecticut River, can be found on the Trail as well as many interesting geologic, historic and natural features.  Unfortunately the trail is difficult to reach by public transportation, but there are workarounds.

More information:
My trip report including information on shelter, food, and transportation

Skyline Trail, Blue Hills Reservation, Milton
Thank goodness for this park and set of trail connected trails in the greater Boston area-- it's a 4 seasons area, and I've enjoyed snowshoeing as much as hiking.  7,000 acres from Quincy to Dedham, Milton to Randolph, and over 125 miles of trails. The Skyline Trail, my favorite, stretches 10 miles across the reservation.  

There are many trail entrances, but the reservation headquarters are at 695 Hillside Street, Milton, MA. There are maps available for $2 contribution at the reservation headquarters.

MBTA Directions: 
The Great Blue Hill and Houghton's Pond sections are accessible from the Red Line to Ashmont Station. From Ashmont, take the high speed line to Mattapan. The Canton and Blue Hills bus services the Trailside Museum and Great Blue Hill on Route 138. For the Houghton's Pond area, exit the bus at Blue Hill River Road. Cross the road and walk one mile east on Hillside Street. 

Car Directions:

Take Route 93 to Exit 3, Houghton's Pond. Turn right at the stop sign onto Hillside Street. Houghton's Pond is located approximately 1/4 miles on the right; Continue 1/4 miles to the reservation headquarters on the left.

More information:

Official DCR Blue Hills site

Downloadable trail map

Skyline Trail, Middlesex Fells, Winchester/Medford, Malden, Stoneham
I am so grateful to the Middlesex Fells reservation for providing so many easily accessible and satisfying hikes.  My favorite of the many paths is the Skyline Trail, a 6.9 mile circular loop marked by white blazes that follows the outer perimeter of the western Fells.  As the website says, "There are spectacular views of Boston and the surrounding area. Most of the Skyline trail is in wooded landscape, with several steep ascents to rocky outcrops. A difficult hike."

Can't resist capturing the initial desire of the Fells:

“What we wanted in the Fells was a bit of Nature in our midst that we might watch its workings...We wanted our tree covered rocks and cliffs that these might lift themselves up by friendly trunks and swing themselves down by branches...we wanted dark, crowded places, even jungles, that we might press through them and come out upon wild pictures which we had never dreamed were there.” 

-Ellen Wright, 1906

 More information:

Friends of the Fells description of Fells hiking trails
Directions to the Fells
Map of the Fells 

Walden Pond, Concord
Three miles of trails ringing around the pond Thoreau made famous.  During the summer and bridge seasons, it's possible to swim in and across the lake-- a great complement, or alternative, to walking.