During the winter months, cross-country skiing and snowshoeing are popular activities at Pondicherry. Although any of the hiking trails may be skied or snowshoed, only the parking lot for the Mud Pond Trail is plowed in the winter. Also, snowmobiling is allowed on the Pondicherry Rail Trail and the Presidential Rail Trail, so use caution if skiing or snowshoeing on these trails.
In addition to the regular hiking trails, there is also a winter-only trail called the Mooseway that runs from the Mud Pond Trail to the Little Cherry Pond Trail. Just under 1 ½ miles in length, this trail is wonderful for cross-country skiing or snowshoeing and is a great place to look for wildlife tracks in the snow. From the Mooseway/Little Cherry Pond Trail junction, one can easily head to Little Cherry Pond or Cherry Pond before returning on the Mooseway to the Mud Pond Trail.