Mt. Tom sports a number of trails, starting from 3 locations in Woodstock and leading to the peak overlooking the village.
If you are near the Woodstock Village Green, the easiest way to get to Mt. Tom is to pass through the Middle Bridge onto Mountain Avenue to Faulkner Park. A series a switchbacks lead you from the Park to the summit of Mt. Tom.
If you are driving, another easy access point is through the parking lot on Prosper Road which you will find here:
A third route up Mt. Tom is through the Marsh, Billings, Rockefeller National Park headquarters which you will find here:
Whichever route to choose, be sure to record its location so, once you visit the peak, you can find your way back to your starting point.