In the 1800s and early 1900s, Acadia University had a farm south of campus. "Over the past fifty years, the old pastures and fields of the Acadia University farm have become covered with forests of trees and shrubs. The Woodland Trails will lead you through century old Birch and Poplar stands, plantations of Norway Spruce, Scotch Pine and Grand Fir, and glades of native ferns along Acadia Brook" - From Acadia's map of the Woodlands Trails. There are still some remains of the farm, including the well at this location.
Trailhead is marked as where the trail crosses Skyway Drive. The whole trail is worth a walk. Parts of the trail can be wet. The map (link above) shows where the different paths of the trial lead. Pictures of the trail, including the well are at this link: virtualtour.acadiau.ca/woodland-trails.html
The cache is sort of winter friendly and sort of not. It could easily be covered by snow, although it is off the ground.
Congratulations to 4CeasonS on FTF!