Sounds like fun, other than the in the city bit. Let us know how it goes.
Any excuse to get outside is good. Last July 4, did 17 mi in 8 hrs @4000-8500 ft in the Eagle Cap Wilderness area, about a quarter was post holing through snow pack, with ~45lb pack.
x2 on footwear. Peanut butter and hydration are your friends
1970 SIIA 88, Sold
1996 Disco I, RIP