Greenwood Park offers access to several trails that explore the diverse habitats and features of the reservation. Visitors enjoy hiking, biking, running, or walking with their dogs in this scenic area that is rich in local history and wildlife. The park is open from dawn to dusk and has free parking available.

The Middlesex Fells is a large tract of land lying only five miles from Boston and inside MA-128. It is accessible through 50 miles of trails and carriage roads and bisected by I-93. Inside the Fells are several ponds, including Spot Pond, three connected reservoirs for the town of Winchester, and several smaller ponds. The Fells’ history includes industrial use for timber, pasture, quarrying, ice, and waterpower. The Fells are largely wooded with mixed deciduous and coniferous second-growth forests that include a hemlock taiga and a sturdy grove of pines at Virginia Wood, and a red pine monoculture surrounding the Winchester reservoirs. A 10-acre meadow is in the Sheepfold area, with several smaller open fields and areas of low, secondary growth.

The site is an important migratory stopover or seasonal concentration site for migratory land birds (e.g., warblers).

The AllTRails website and the Gaia GPS website have descriptions and maps of hikes at Greenwood Park.