Great Blue Hill via Skyline Trail is rated as moderate on AllTrails. The trail involves scrambling up and down both large rocks, and works almost in a pattern: you ascend to a point by walking up a large rock, walk a path on level ground for a bit, then descend via rocks on the other side. The up-and-down nature of the trail provides a solid yet manageable workout, and at a few different points the climbs are rewarded with beautiful views overlooking the treetops.
The hike winds through a couple of different observation points. The first is Eliot Tower, a stone structure from where Boston can be viewed. There are also several spots surrounding the tower that provide shade and picnic tables. We continued on the trail a few hundred yards more to ascend the Great Blue Hill, which is marked by the Great Blue Hill weather observatory at the top. Here, we paid $4 each to go to the top of the observatory, where we had a 360 degree view that included all of Boston. The guide pointed out that on days with optimal visibility, Providence and Mount Monadnock can also be seen.
The latter half of the loop was much easier, but the descent did become steep. At points we had to grab onto trees or place our hands on the ground in order to navigate the path without losing our footing and tumbling down the path. Still, at no point did we have to traverse something that would be exceedingly difficult for the average person.
After the hike, we headed over to Canton, to one of the most popular breweries in Massachusetts, Trillium Brewing Co. Unfortunately Trillium wasn't offering their patio draft service on that day, so we had to settle for curbside pickup.
Trillium has a series of fruit sours called Daily Serving which are some of the best sours out there. The concept is simple: it's your daily serving of fruit, in beer form. Today the flavor on the menu was cherry, but it's always rotating: Raspberry, Pomegranate and Blackberry, Tropical Punch. They taste like juice. My dad would say it's not real beer but I promise you, it's a good stuff.