Start out by walking the short distance from Roslindale Village to Arnold Arboretum, the famous outdoor botanical garden which is owned and maintained by Harvard University. There's a magnificent view from Peters Hill at the southern end of Arnold Arboretum, and another from Bussey Hill if you choose to detour slightly off the line shown here.

In contrast to the big views, walking alongside the trickling water of Bussey Brook is lovely, and leads from Arnold Arboretum to Southwest Corridor Greenway and then Franklin Park. The park feels remarkably quiet despite its proximity to the city centre, and you can immerse yourself in nature before a brief section of urban hiking leads to Jamaica Pond and its charming boathouses.

Sources -

https://www.bostontrails.org/

https://www.masslive.com/boston/2022/06/bostons-walking-city-trail-how-to-hike-25-miles-through-the-city-while-discovering-hidden-gems.html#:~:text=on%20the%20trail.-,The%20Walking%20City%20Trail%2C%20the%20brainchild%20of%20Miles%20Howard%2C%20is,even%20a%20jaded%20hiker%20interested.