I went down to Richmond to ride from Richmond to near Williamsburg and back today. The ride supports the Virginia Capital Trail Foundation. The routes were 100, 50, 25, 15 (Williamsburg only) but the nice thing about this ride is you can start from either Richmond or Williamsburg. All total there were around 2000 people riding.
The good thing is the time I did it in. It is definitely a ride I would recommend. Very little wind, but it is early in the season for a some to do a century. The terrain was around 2000 feet of climbing for the century (calculated by my GPS).
This started with a mass starts and each of the distances started at a different time. .The rest stops were spread out every 12-15 miles. Well maintained, and well managed. there were groups for everyone to ride with.
