Looking to venture off the trails

Riding roads in outside-the-beltway VA kinda sucks (until you get to the gravel stuff in Loudon County). I would ride out the W&OD to Leesburg, go up 15 to Whites Ferry then hit Sugarloaf and ride back on the MD roads. I recommend something like this: https://www.strava.com/activities/63842222 — that was a lot of fun and right in your target mileage.

Edit: note that there’s a little detour off the trail there that you’ll want to clip out

Here are some cleaner options:
– https://ridewithgps.com/routes/2774024 – I think this was route used for ride above.
– https://ridewithgps.com/routes/6209823 – This one skips Sugarloaf for some of the nicer roads on VA side — does include a bit of gravel; we were just on 25mm road tires, though.