Mount Tom is the prominent hill overlooking Woodstock, and its low summit has great views over the village and to the Green Mountains to the west. (It's part of the Marsh-Billings-Rockefeller National Historic Park.) You can ascend the mountain right from the village: Start at Faulkner Park, named after Mrs. Edward Faulkner, who created the park and had the mountain trail built to encourage healthful exercise. To reach the trail head from the green, cross Middle Covered Bridge and continue straight on Mountain Avenue. The road bends left and soon arrives at the grassy park at the base of Mount Tom.
The trail winds up the hill, employing one of the most frustrating sets of switchbacks you're likely to experience. Designed after the once-popular "cardiac walks" in Europe, the trail makes hikers feel they are walking miles only to gain a few feet in elevation. But persevere. This gentle trail eventually arrives at a clearing overlooking the town. A steeper, rockier, more demanding trail continues 100 yards or so more up to the summit. From the top, follow the carriage path down to Billings Farm or retrace your steps back to the park and village.
