Check out the Tacoma Wheelmen (twbc.org) for some local rides--mostly an older crowd there--the club has been in existence since 1888. Usually 2-4 rides to choose from over the weekend. Also the Cascade bicycle club has tons of rides, mostly based out of the Seattle, North end area, but they are a much larger (and more politically active) groug with more organized rides. (
www.cascade.org) Usually a dozen rides to choose from over the weekend. Good local LBS are spoke and sprocket in university place.(
http://www.spokeandsprocket.com/) They also do a regular club ride on Saturdays 8:00, anyone is welcome. Also another good LBS is Old Town, they have two shops one in Gig Harbor and one in Old Town Tacoma. (
http://oldtownbicycle.com/). My local favorite is Rainier Cycle in Proctor (Tacoma)--its walking distance to my house. (
http://www.rainiercycle.com/index.htm) For rainy weather get fenders and full-fingered gloves and avoid manhole covers, painted lane markers, and RR tracks. Topography: generally steep hills near the water 2-300 ft, but lots of river valleys for flat riding. Near my house, its flat in tacoma, but as you get towards the water there are steep hills of short duration 9-11% grade and 1/3 mile or less. You can ride across the bridge now, which is a bonus, because ther is very good riding in Gig Harbor and lands north. Good Luck.