Do you ride gravel/mountain?
Follow the Outpost on socials, they host gravel rides pretty regularly.
There’s a regular MTB ride out of Basic City on Thursdays. Coqui does MTB rides on Weds. Vasen has an MTB ride on Sat mornings (I think).
Folks have mentioned CBC, good rides sat and sun. I think outpost does a rotating gravel/road ride out of the shop on Sat mornings.
If you do ride Gravel, Virginia Endurance Series will start up in late Jan/early Feb. Look for them on Facebook. Series of very fun, free gravel rides mostly out in Charlottesville, Harrisonburg areas. Highly recommend these.
If you don’t ride mountain, it’s great place to start, you can string together 50 miles of trail riding in the city, Pocahontas state park has another 40ish and Charlottesville, Roanoke and Stokesville are a blast.