Tippling Rock Trail Head This 1.4-mile out-and-back trail is generally considered moderately challenging and takes an average of 38 minutes to complete. The trail is generally wide and well-used with moderate slopes for much of the distance, though some bends and steeper sections make it challenging at times, with a very steep final approach to the top aided by wooden logs and rock steps. The property features hilly topography marked by numerous rock outcroppings, rich woodlands, and prolific vernal pools. The elevated rock formation rewards hikers with a scenic view looking east toward Boston and Mount Wachusett to the northwest. In spring, there is a little waterfall beneath Tippling Rock. Tippling Rock is steeped in folklore, with some commentators proposing that Native Americans moved a large boulder back and forth on top of the outcropping in an action referred to as “tippling.”The trunk trail is a small segment of the much larger Bay Circuit Trail.