There are two independent bike shops in Caledon and we try to patronize them both to help keep them around. If they don't have something in stock, they are great about ordering things in if they have relationships with the supplier, especially for customers they have come to know. I've even done it with things like bike shoes where I needed to try two sizes, although that's not always possible. They usually can't afford to keep high end bikes in stock but they'll order them in. One of the problems they have is that some people will do their research at the local shops, then buy something online or in Toronto, so it isn't cost effective to keep too much expensive inventory.
Btw ordering stuff in is something we do a lot in a small town to support local merchants. E.g. we get the ISBN for a book at the Chapters website, then we order it in at Forsters Book Garden in Bolton, an independent bookstore.
1) The closer bike shop to you is Caledon Hills Cycling in Inglewood. Just hop on the rail trail and hop off when you get to the Inglewood train tracks. CHC is a few buildings north on the west side. Friendly people - say hi and get to know them! They lean more toward mountain bikes and they carry a fair amount of outdoor bike/hike gear and clothing, GoPro gear, race snacks and drinks, and skis and snowshoes in winter. They can tell you about the MTB trails you can access just west of them on the escarpment. In the winter, they have a very popular Wednesday night hike, often on snowshoes, often followed by a pub visit. They are loosely affiliated with the Caledon Cycling Club, which has group rides and events, both road and MTB.
(No local bike shops ever update their websites!)
2) North Hub Bike Shop is at the south end of Bolton near Home Depot. It's a smaller shop that made a transition within the past year to focus on biking instead of biking and running both. (It was called "Walk Run Ride" before.) They have some bike accessories, shoes, trainer DVDs, snacks and clothing although not as much as CHC. They have a good mechanic but the last time I was there, he was not working every day. They have a studio in the back where you can bring your own bike during the winter and do classes on their trainers with power meters. They also organize some group rides. They are more road bike oriented but also carry some MTBs.
3) Some riders swear by Epic Ride in Orangeville, especially for complex repairs. They have a small retail shop and they also organize group MTB rides.