We love walking dogs in Weston. Jericho Town Forest is a great location and dogs can be unleashed if you live in the town. Any dog walkers must have a permit and dogs still need to be leashed entering and exiting the trails.
Dog walker covering the Weston, MA area
Another great spot that you can meet a lot of people Cat Rock. Gets pretty busy during the warmer weather but has great hiking trails. The same rules apply above.