Legacy Trail and Connector Paths

The Legacy Trail is the result of many generous contributors during Weston's Tercentennial Anniversary in 2013. The Weston 300 (the Tercentennial Steering Committee) hosted a year-long celebration with events honoring Weston's history and community as it also raised the funds for this lasting gift. The trail was originally supposed to be located on the Case Campus but after the 10-year acquisition battle for the Case Estates concluded in 2016, the Legacy Trail was relocated so everyone could enjoy the spectacular views of this historic property. 

Town Meeting in 2019 approved additional funding through the Community Preservation Act fund for the construction of the trail and  the connectors. The paths meet US Forest Service Trail Accessibility Guidelines (FSTAG) standards and are permitted by the Massachusetts Architectural Access Board..

The new paths include:

  • the Legacy Trail (0.3 miles, paved)
  • a connection to Wellesley Street (0.1 miles, stone-dust)
  • a path connecting Wellesley Street to Ash Street (0.3 miles, stone-dust). 

The Legacy Trail also connects to other pre-existing trails at the Case Estates and on abutting Town land, allowing visitors to further explore this beautiful area. 


The Legacy Trail is dotted with dedication pavers and benches (for resting along the way), a sitting area at a scenic overlook where the Summer House used to be located, and a compass rose dedicated to the memory of former Conservation Commissioner and treasurer of Weston Forest and Trail Association, George Bates. All five trail-head markers and the two pillars at main entrance are made from historical granite repurposed from the old Sears Estate and the Field School. 

Trail Notes and Map

Dogs must be leashed at all times on the entirety of the Case Estates and abutting conservation land. This is to preserve the sensitive surrounding meadowland ecosystem and ensure access to users who are not so comfortable with a canine companion. 

The trailhead is located on Alphabet Lane across from the Council on Aging (Lower Community Center entrance), where parking is available.  A Case Estates Trail Map (PDF) is available for downloading.