Tipling Rock Trail (Weisblatt Property)

Published June 5, 2014 | Sudbury | Updated June 13, 2023

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The Tipling Rock Trail/Weisblatt Property was acquired in 1998. This is a property of hilly topography marked by numerous rock outcroppings, rich woodlands, and prolific vernal pools. The property has trails which lead to Tipling Rock, a popular destination which features an elevated rock formation with a scenic view east toward Boston. At over 600 feet above sea level, Tipling Rock is the highest point on the Sudbury portion of Nobscot Hill. Boston and Mount Wachusett are visible from Tipling Rock. Although Tipling Rock is not part of the Tipling Rock/Weisblatt property, hikers may access the rock through trails along the Tipling Rock/Weisblatt property.

Tipling Rock is steeped in folklore. Some commentators have proposed that Native Americans moved the boulder back and forth as a means of communication. The boulder on top of the outcropping used to tipple or rock back and forth. Thus, Native Americans would tipple it to send sound through the rock for communication. Tipling Rock also offered Native Americans an advantageous view of the countryside.

The rock shows evidence of wedge or drill holes. Historians have proposed that the rock was blasted by the late John Bartlett and his brothers. Others have speculated that a farmer leasing the field may have blasted the rock because cows could be injured by the tippling rock. Another theory is that rock was split to make a mill stone. There were further attempts to destroy parts of the rock in the 1930s.


Parking is available off of 641 Boston Post Rd.

Trail Challenges

The trail is generally wide and well used. The trail is moderately sloped for much of the distance to Tipling Rock. There are some bends and steeper parts of the trail, which make it moderately challenging. There is a section of the trail that is flat and wide, but the trail continues upward again as it approaches Tipling Rock. At Tipling Rock, the climb is very steep with wooden logs set into the ground as steps. There are rock steps also. This is a challenging part of the climb. Although Tipling Rock is very large, it has some dangerous areas where the rock falls off with steep drops.

Trail Comments

  • “The wooded trail is very beautiful, but it is a constant upward slope.”
  • “This is a favorite trail for people in the area. Tipling Rock is a great experience.”
  • “The climb up to the rock is tricky. There are steep areas with logs and rocks used as steps.”
  • “The hike is really worth it once you see the view from Tipling Rock. It is really spectacular. You can see all of the land toward Boston. You can even make out the Hancock Tower.”
  • “Tipling Rock is very scenic. There is a panoramic view of Boston and the land east of Sudbury. This view is hard to match anywhere.”

Trail Videos

   Tipling Rock Trail – Highlights

   Tipling Rock Trail – Trail Hike

Trail Photographs

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