We ride from the shop I work at (off the Boulevard in downtown Richmond) occasionally. We are planning to put some more formal group rides together on Saturdays or Sundays this spring and summer, because we have a bunch of friends and customers with bikes. You can get directions to our place on the bottom of the main page at http://www.rosenautosport.com
There are also unofficial group rides from Moto Europa/Ducati Richmond on many weekends. You can get directions to their place at http://www.motoeuropa.com
if you haven't been there to drool over the fine Italian machinery yet. :-)
I'm sure you also know about the "Bikes in the Bottom" meets on the second Sunday morning of each month. Riders gather in Shockoe Bottom (downtown, you know, the bar district) and ride all over the place before or after brunch. When the weather is nice, you might see as many as 100 bikes at one of these meets - everything from cruisers to race bikes, and even cheap/boring commuter bikes like mine. :-)
As far as routes go, I'm a big fan of Route 5. It runs from downtown Richmond for about 60 miles right into Williamsburg. It's two-lane with some nice fast twisties. On the other side of town, Routes 6 and 250 are both nice 60-70 mile rides to Charlottesville with some nice fast twisties as well.
Anyway, contact me privately if you want to know about our next group ride from the shop. I think we will do one sometime in April. Or let me know if you're going to the next Bikes in the Bottom, and I'll see you there!
Jon (aka "getfast")
92 GS500E beater,
saving up for an SV650