We are huge fans of the Trustees of Reservations. They do amazing work making nature available to the masses while simultaneously preserving historic buildings and promoting the history of Massachusetts. The Bradley Estate, with its 90 gorgeous acres, is no exception. It’s immaculately kept, convenient, and beautiful. The estate hosts weddings from May to October, features amazing gardens in the spring and summer, and offers a wooden reindeer hunt and holiday light walk-through in the winter. Located near Route 95 and the Blue Hills, the Bradley Estate is easy to get to. Parking is a breeze (although it costs $6 if you’re not a member of the Trustees), and you really cannot get lost here, which makes this property a much less intimidating option than the Blue Hills across the highway. Speaking of the highway, that is the one downside to this spot–you will hear the constant hum of cars during your whole hike. However, after a while, it becomes white noise, and you’ll be more focused on your burning calves–this property has a fair amount of steep hills!