Back in CT where I started cycling, there was pretty much only one shop I went to, until they moved and changed owners, which coincidentally was the same time I moved up to school. Now when I go back I go to another shop, which feels a bit friendlier, but still not as awesome as my shop now. Plus, they're never open when I'm at my parents.
When I went to school I lived behind and a street over from a bike shop, which means convenience was the key. I kept going to that shop, and that shop only until I realized they would never change. Neither of the owners seemed to ride, and they never hosted rides. This turned into a big deal since I was forever looking for someone to ride with.
A couple years later (last October) I started looking for a place to bring the bike to for a tuneup. There are four bike shops in Beverly (Google says five, but one went out of business a couple years ago). The first is the one I wasn't happy with, the second is right down the street, and though I've never gone in, I never will. They reek of elitism and trendy, with all those heavy 'beach cruisers' hanging in the window. No thanks. The third I went in to check out, and though it was new, it was way too clean (seriously, bikes are dirty things!), the prices were high and I got a strange vibe. The fourth is my shop of choice, Beverly Cycles.
I went in there on my way back from shop #3 on a whim, and have been back there at least once a week (lately almost everyday). First thing that happened when I walked in was Bill, the owner, asking if I wanted to make myself a sandwich. Then we bullshitted about everything except bikes. Then we actually talked about bikes, and found out his rates, and I had found my new shop. By the third trip I felt like part of the family.
Oh yeah, and they host rides, so far inside, but outside rides are forthcoming. I've met a lot of great friends, and I can't imagine making another shop the place to be Mon/Weds and Fri nights. I even have a nickname.
So, do you have shop loyalty? Does your shop know who you are?