We love walking dogs in Dedham. Blue Heron Trail is a great location and dogs but they must be kept on leash here. It's about a 6 miles of hiking.
Dog walker covering the Dedham, MA area
Another great spot that you can meet a lot of people and their fur babies is Mill Pond Park. Gets pretty busy during the warmer weather but has great hiking trails. The parking is not that great but it does have a bench at the pond you can take a break on.