We have a pretty active bike club - http://brbcva.org/ They do organized rides (on and off road) several times a week. There are plenty of good routes around here.

We are lucky enough to have quite a few good bike shops here as well:
http://www.cardinalbicycle.com - carries Specialized, Giant, Raleigh - some high end stuff, but mostly entry level and kids stuff. Good selection of helmets/clothes/etc.
http://www.eastcoasters.com - carries Trek, Gary Fisher, Guru, Serotta and I think a couple more. Good mix of low and high end stuff. They do great bike fittings, and support a lot of local racers
http://www.justtherightgear.com - carries Cannondale, Santa Cruz, Kona, Surly, Niner, and some other nice brands. They are a couple miles from the most popular mountain biking area in this area
http://www.starlightbikes.com - mainly carries track/fixed gear stuff, but also carries some higher end road stuff. They are very involved in the racing scene around here as well.
http://www.3peaksshop.com - mainly a tri store, but carries a good range of road bikes. I know they carry Blue and Fuji. Not sure what other brands