The hike begins on the wooden planks of the Harvest River Bridge and the trail then winds through suburbia before reaching Sherrin Woods, just to the north of Hyde Park. After passing through Hyde Park, one of the more tranquil sections of the whole trail awaits as you cross Stony Brook Reservation. There are some great views towards Boston city centre from Bearberry Hill (in the heart of Stony Brook Reservation) and it's fun to glimpse where you're heading over the next few days.

From Bearberry Hill, drop down onto Washington Street and stroll easily into Roslindale Village, where you can either stay for the night or get into the Boston public transit system.

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.