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Tippling Rock Trail


June 5, 2014

| Sudbury
| Updated

March 6, 2024

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The Tippling Rock Trail/Weisblatt Property was acquired in 1998. This property features hilly topography marked by numerous rock outcroppings, rich woodlands, and prolific vernal pools. The property has trails which lead to the Tippling Rock, a popular destination. This elevated rock formation rewards hikers with a scenic view looking east toward Boston, and Mount Wachusett to the northwest. At over 400 feet above sea level, Tippling Rock is the highest point within the Nobscot conservation lands lying within Sudbury. Although the Tippling Rock itself does not lie within the Tippling Rock Trail property, it can be accessed via the trailhead off of Boston Post Road.

Tippling Rock is steeped in folklore. Some commentators have proposed that Native Americans move a large boulder back and forth on top of the outcropping, an action referred to as “tippling”. The noise thus generated could be used to communicate over long distances. Tippling 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 to prevent his cows being injured by its movement. Another theory is that the 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 trunk trail is a small segment of the much larger Bay Circuit Trail. When completed, it will connect a 200-mile greenway corridor connecting 50 cities and towns in a broad arc around the Metro Boston area. Generally wide and well-used, it is moderately sloped for much of the distance to Tippling Rock. There are some bends and steeper parts of the trail, which can make it moderately challenging at times. Some of the trail that is flat and wide, but the approach to the top is very steep, with wooden logs and rock steps set the ground to aid your ascent. Climbers should remain vigilant, as there are some 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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