The new sister trail to the Walking City Trail. Different, but really great. Meandering through neighborhoods to visit various nature spots and views of the city from all different perspectives. Much more pavement than the original, but lots of cute pathways and staircases galore. Begins with a delightful trail through the forest (recommend waiting till after sunrise, so you could actually see and not violate my rule of hiking in unfamiliar woods in the dark by myself, particularly if going around cementeries!). I startled three deer (and got startled myself!), saw about 15 turkeys, and an infinite number of bunnies. There were a few other woods trail sections early on, then a long section wandering through neighborhood paths. Trail runners weren't necessary, haha. Actually kind of looked forward to roads as they were easier and quicker to navigate, and didn't have a ton of spider webs! A dichotomy from running by the mansions of chestnut hill first and then Roxbury and Dorchester neighborhoods. Refilled water and bathroom break at the stop n shop slightly over halfway. Also had a Starbucks stop 8 miles in. The last portion is the paved, flat Boston harbor trail which can be run more quickly, with the notable exception of the final steepest climb up to the Boston National Historic Park and Dorchester Heights Monument. I think the last time I ran the causeway out to Castle Island I was getting ready for the AsMA 5k and did sub 7 min miles...tired much harder today, but wasn't close, haha. I think this beat the fkt/okt by about 15 min, 6:28 vs 6:45 total time including store stops (wasn't originally an FKT route, so waited a year+ to upload). Had perfect weather, sun came out but was mostly cool and stayed dry, albeit usual Boston humidity. Legs felt decent for second 30+ miler in a week. Huge props and thanks to Miles and others involved with putting these trails together, it's an incredible series of trails, sights, and destinations. I spent most of my run contemplating how he managed to link so many neat spots up, all while maintaining public transportation access to each "segment". Also thanks to my two Uber drivers who didn't ask questions why I was going to an empty, remote park at 4:30 am or then why I was so sweaty and smelly. https://www.bostontrails.org/cityonthehillstrail