The 115-acre Holbrook Town Forest is located in Northeastern Holbrook. It was founded in 1955 on undeveloped land. There are several trails, winding around the glacial rock outcroppings and forested wetlands; it is a pristine place to hike or snowshoe. Enter either from the end of Forest Drive or 255 Pine Street. Maps are available at the Conservation Office at Town Hall. 

Cranberry Pond Conservation Area is located adjacent to and north of Holbrook Town Forest.

Holbrook Town Forest trails include:
Wiggins Trail
Wiggin Trail is the most popular trail. It runs south to north and is blazed with red squares. Enter at the McKay-Sodergren Entrance at the end of Park Drive, or at the Mann Entrance at 75 Pine Street/across from the old Fire Tower. This trail enters Braintree just after the High T’s, and from there you can make your way to Cranberry Pond.
Long Trail
Long Trail celebrates its 50th anniversary this year. It is perhaps the most varied and pretty of all the trails, and begins at 255 Pine Street, at the Carolyn Long Entrance. It is blazed with blue circles. You travel east until crossing Wiggin Trail, and eventually proceed south until you rejoin Wiggins. A nice loop is made if you walk back up Wiggin (headed north) until picking up Long Trail again on your left.
Elfin Pond Trail
Elfin Pond Trail begins a short way down Wiggin trail, to the right. It is marked with yellow squares and circles Elfin Pond, a large certified vernal pool.
Boundary Trail
Boundary Trail is marked with orange circles. It begins at the Mann entrance at 75 Pine Street. It travels past Elfin Pond.
Sawyer Trail
Sawyer Trail is blazed with white triangles, and Estes Way is blazed with orange squares. Both connect the Long Trail to the Elfin Pond Trail.
Diman Trail
Diman Trail runs off of the Long Trail before you reach Wiggin. It is marked with yellow diamonds, and if you follow it north toward the high T’s there is a pretty spot to rest.

The AllTrails website has a description and map of a hike at Cranberry Pond Conservation Area.