Ah, the east side--a great place to live for almost every but getting out and riding varied distance rides. Every time I think about moving back to the east side I remember riding around and around in circles....down the lake front, up by the tennis courts, through the park, down the lake front....

Don't let lack of experience scare you away from a group ride--everyone starts somewhere. I suspect the W&S ride is very low key and people I've talked to from TriWi have been nice. One of the nice things about east side riding is that once you get up off the lake, the terrain is pretty flat. That pretty much elminates getting dropped on a hill climb

Also on Apr 27th, Bay View starts out of Kletsch Park which is just a bit north of you, up the Milwaukee River Parkway. As I was driving home tonight, I realized I should have sent you to Rainbow Jersey (my guess was you were east side)...looks like you already found them. Eons ago they were my favorite shop (now they're too far away). I'd probably ask them if they had suggestions for lower key rides than Hampshire.

But really, jump in and try the group rides. Now is the best time--everyone is out of shape and out of practice. Good luck!