Because I thought I could
Join Date: Dec 2004
Location: Wash DC Metro
Bikes: November, Trek OCLV, Bianchi Castro Valley commuter
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I'd check the area's cycling clubs (Richmond, C'ville for the Rt 250 question, Potomac Pedalers - there is an active but unofficial google group - for Front Royal to DC) for route suggestions; I believe there have been discussions on getting to/from Front Royal (Skyline Drive) and the DC area. Looking at your route, I see you go past the Rt 50 end of Blue Ridge Mountain Rd, so the PPTC cue sheets for "the Blue Ridger" (or anything involving Mount Weather) may have some useful suggestions for you. I've been on/near Rt 50 in Upperville, but I don't know how good/bad Rt 50 is to get over Ashby Gap - I've looked at the Rt 7 crossing (other end of Blue Ridge Mtn Rd) and rejected the idea. Blue Ridge Mountain Rd (if you like more hills!)-Rt 7-Snickersville and Snickersville Tpk and the swing north (your route) to Round Hill are fine. I think I've been on most of your route from Rt 50 (Upperville) to Round Hill and Purcelville, so it's rideable; I don't know how good/bad Rt 50 is in that section. If you want to try some of the county side roads, many in that area are gravel. Not good on 23mm tires, probably OK on 32 mm. If you need a bike shop, Trails End Cycles is in Purcelville at the western end of the W&OD. They may have suggestions for Front Royal to P'ville.
Once you get into Loudoun County and the DC suburbs, I'd give up on stealth camping. Sky Meadows State Park has primitive camping (watch out for the ticks!) and there may be stealth possibilities on/near the Appalachian Trail (Ashby Gap). W&OD: There are some cyclist-friendly eateries in Purcelville (ask Trails End) and in Leesburg (just north of the W&OD between Dry Mill Rd & King St - turn left at the little gazeebo and go a block or 2 north). Carolina Brothers (formerly Partlows) in Ashburn (W&OD Mile 27.5) has beef, chicken, and pork BBQ to die for. Herndon (W&OD Mile 20), there is a Dairy Queen alongside the trail and Great Harvest Bread (free slices, cyclist friendly) around the corner. Bike Lane (Reston Town Center/Mile 18) and Performance (about a block off @ 17.5) and Spokes Etc & Bikes@Vienna in Vienna (Mile 11?). If you run out of steam along the W&OD, Lake Fairfax Park in Reston has cheap tent camping (and SHOWERS) and is not far from the W&OD. You'll need to enter from the north (any bike trails marked from the south are MTB) and side road access is much calmer than Baron Cameron Ave. Lake Fairfax is your last camping opportunity. DC is about 17-18 miles at that point via W&OD and (@ W&OD mile 4) the Custis trail through Arlington. Mind the street crossings on the W&OD and Custis and the dread S-curve of death (you'll know when you are there) on the Custis. Have a great trip!