The Shenandoah Valley trip is though the back roads in Virginia. It starts in Waynesboro and travels northeast on US 340. There is a slight detour through Grottoes, VA due to a glitch - actually I selected "Shortest distance" route - in my GPS programming.
The route crosses into West Virginia for a short time then back into Virginia for about two miles until crossing the Potomac River and into Maryland.  Check the bottom of the page for the Youtube Video!
DIRECTIONS FOR THE SHENANDOAH VALLEY RIDE
   
Starting out at sunrise from the Super 8 motel in Waynesboro, Virginia to US-340 N/Lord Fairfax Hwy - Maryland State Linew
Red Top Orchard Rd
    
1. Head west on Red Top Orchard Rd toward Apple Tree Ln 
    
2. Turn right onto Apple Tree Ln 
    
3. Turn right onto Lew Dewitt Blvd     
4. Take the 1st left onto Rosser Ave 
    
5. Turn right onto W Main St 
    
6. Turn left onto US-340 N/N Delphine Ave
Continue to follow US-340 N
7. Turn left onto State Route 778/Harriston Rd
Continue to follow State Route 778
8. Take the 3rd right onto State Route 825/S River Rd
Continue to follow State Route 825
9. Turn right onto VA-253 E/Port Republic Rd 
    
10. Take the 1st left onto State Route 1603/Lower Ford Rd 
    
11. Slight right onto State Route 955/Jacksons Way
     
12. Turn left onto US-340 N/SE Side Hwy
Continue to follow US-340 N
13. Turn right onto US-211 E/US-340 N 
    
14. Take the US 340 N/US 340 Business S ramp to Luray/Front Royal 
    
15. Turn left onto US-340 N/N Broad St
Continue to follow US-340 N
16. Turn right onto E 6th St 
    
17. Continue onto Happy Creek Rd 
    
18. Continue onto State Route 624/Morgan Ford Rd 
    
19. Turn right onto State Route 624/Milldale Rd
Continue to follow State Route 624
20. Turn right onto State Route 624/Red Gate Rd 
    
21. Continue onto VA-255 N/Bishop Meade Rd 
    
22. Turn right onto VA-255 N/Bishop Meade Hwy
     
23. Turn left to stay on VA-255 N/Bishop Meade Hwy 
    
24. Turn right onto US-340 N/Lord Fairfax Hwy     
    
US-340 N/Lord Fairfax Hwy
110 mi, 2 hours 47 mins
US-340 N