There is a significant network of interconnecting shorter trails on Mount Wachusett and in the Ware River Watershed area maintained by the Massachusetts Department of Conservation and Recreation, the Worcester Chapter of the Appalachian Mountain Club, and the nonprofit organization Wachusett Greenways, including an 8.8 miles (14.2 km) section of the Mass Central Rail Trail.

[2] The Midstate Trail corridor includes woodland, lake shores, ledges, swamp borders, small mountains, agricultural land, meadows, brooks, as well as a few classic New England hamlet commons.

The highest point on the Midstate Trail is the 2006-foot (611m) summit of Mount Wachusett from which the Boston skyline, 45 miles (72 km) away, is visible in clear weather.

[1][3] Notable features that are on or are easily accessible from the trail route include Wallum Lake, the French River (Massachusetts), Hodges Village Dam, Buffumville Lake and dam, the historic Ryder Tavern, Moose Hill, Sampson's Pebble, the ruins of an early 20th-century work camp for prisoners with tuberculosis, Barre Falls Dam, the Massachusetts Audubon Society's Wachusett Meadows and Burncoat Pond sanctuaries, Mount Wachusett (the most prominent peak in eastern Massachusetts), the Crow Hills (a popular rock climbing destination), Muddy Pond (an attractive, remote, and undeveloped glacial pond), and Mount Watatic, the southernmost prominent summit in the Wapack Range of mountains (sometimes referred to as the Pack Monadnock Range).

[1] Although the trail is most often used for hiking and occasionally snowshoeing and backpacking, portions of it are suitable for, and are used for, mountain biking and cross country skiing.

[4][5] The Midstate Trail passes through land in the following incorporated towns: Douglas, Sutton, Oxford, Charlton, Spencer, Leicester, Oakham, Rutland, Barre, Hubbardston, Princeton, Westminster, Ashburnham, and Ashby.

[3][6] Southern portions of the Midstate Trail traverse a terrain marked by rock outcrops and ledges of gneiss and schist, and occasionally granite.

Northern portions of the trail (especially Mount Watatic) follow mountainous ridges of 400 million year old, heavily metamorphized schist and quartzite identified as the Littleton Formation.

The extremely steep south and/or east faces of these hills were carved by the movement of glacial ice down lee slopes.

Common species include American beech and yellow birch at higher elevations and on north facing slopes.

Red, white, and black oak, sugar maple, and ash are prolific throughout, including frequent very old individual specimens often called wolf trees.

The forest understory supports mountain laurel, witch-hazel, wintergreen, hobblebush, partridgeberry, as well as a variety of herbs, ferns and mosses.

In the winter and early spring, ice is a common danger on steep slopes and ledges, sometimes making portions of the trail unhikeable without special equipment.

[1]The trail passes through public land (state forests, parks, and wildlife management areas; federal flood control projects maintained by the U.S. Army Corps of Engineers, etc.

Recent changes in land ownership and encroaching suburban sprawl in Worcester County, Massachusetts have presented significant challenges in maintaining the continuity of the trail route and its scenic viewshed[11] Stands of old growth hardwood forest near the Midstate Trail on the slopes of Mount Wachusett became a magnet for controversy in 2003 after a court ruling in favor of the Commonwealth of Massachusetts in joint contract with a privately owned ski resort regarding plans for a ski slope expansion into an environmental buffer zone around the old growth stand.

A communications tower service road had been blasted part way up the side of the mountain before the conservation efforts were finalized, illustrating the immediacy of the challenges present in preserving the Midstate Trail and its landscape.