You would think living in any city like Boston, finding an isolated trail meandering through the wilderness would be a long way off. I feel it, the dog feels it, a call to the wild. For us city dwellers, it is great if you have hours to head to Vermont to lose yourself in the Green Mountains. Otherwise, with busy schedules and errand days, look to the Skyline Trail in the Middlesex Fells Reservation. Find it, follow it and momentarily forget the hustle and bustle of Boston. You will have a chance to view Boston’s skyline, but from a peaceful distance in your wilderness solitude.
Yes, there are other places to hike with your dog near Boston, but this special dog friendly hike is just a few exits north of the city. I recommend starting at the Sheepfold parking lot and letting your dog socialize in the off-leash area at Sheepfold with the other dogs before disappearing into the woods. Bring water, poop bags, something to put bags of poop in and a sturdy set of shoes (The Skyline Trail is rocky). Then prepare to lose yourself for the woods.