South of Worcester on the tri-state border, the 4,600 acre Douglas State Forest has 30+ miles of trails and jeep roads. The forest is on a plateau with no major hills and a total elevation variation of around 300 feet. Many of the trails are very rocky and luckily, they connect with several double-tracks and gravel forest roads.
To reach the horseback riding trailhead, follow US395 south. Just north of Connecticut, exit onto SR16 at Webster. Proceed east on SR16 for 5 miles into the DSF. At the Cedar Street crossroad, turn left towards the Wallis Street parking area near Whitin Reservoir. (A right turn would lead to the DSF HQ where maps are available.)
To reach the trailhead from the Mass Turnpike US90, use Exit 10. Follow US395 south to SR16. Follow SR16 for 5 miles and follow signs.
Overall, Douglas State Forest is the 8th most popular horse trail of all 23 horseback rides in Massachusetts.