When extending your bike ride west past Leesburg, the terrain opens to over ten miles of rolling hills, horse farms, and vineyards. Yes, this is your first chance to visit wineries on the W&OD and there are three not too far away. theCompass Winery, Brewery, and Distillery Locator mobile app is a major help on this trip. Dry Mill Vineyards & Winery is your first chance and you have two options to navigate. First, take a left on Dry Mill Road from the bike path and pedal the narrow winding road to the winery. The other is to ride to the Fairgrounds and make a u-turn on to Dry Mill Road and back track - in any event this is where you will return to the trail when continuing west. The winery pours a couple nice Chardonnay's - perhaps with live music in the background. 
Casanel Vineyards is the next stop and you may need a break after climbing Clark's Gap. Follow the signs by staying on Business Rt 7 with a quick left on Canby Road. The winery is just over one mile further, but beware - the paved road turns to gravel. Once you arrive at the winery, relax in their brand new tasting room and enjoy the Don Lorenzo, Pinot Gris (75%) and Chardonnay (25%) blend.
When returning to the path, it's only a few miles to Hamilton Station Road. Turn right and the Barns at Hamilton Station Vineyards
is only a short ride away (be alert for vehicles -> they seem to
exceed the speed level). Like the previous two, live music is on the agenda, as well as more refreshing wine (is it time for Viognier yet?).
From Hamilton Station Road, it's only 4 miles until the sidewalk ends at Purcellville. I can't seem to help myself with that one. On Saturday's a winery from DC's Wine Country is usually pouring in the train museum or have a seat at bike friendly Magnolias at the Mill.For the more adventurist, it's time to visit Loudoun County's first post-prohibition distillery: Catoctin Creek Distilling Company. Just take a left on 21st street until it dead ends on Main Street. The distillery provides tours of the facility as well as sample flights, including a cocktail flight sometimes poured by a bartender from DC. I'm a rye type of guy, so the Organic Mosby's Spirit® or Organic Roundstone Rye® fill my needs. 
For lunch, I chose to return to 21st Street, ride past the train station to Monk's BBQ. They just opened this brick & mortal location after selling from their food truck for the past few years. Monk's sells quite a few craft beers to pair with the meat; or take to go and eat at two breweries in the area: Corcoran Brewing Company and Adroit Theory Brewing Company. The latter will be the first you meet after continuing on 21st Street and turning right on Hirst Road (look for signs on the right to find the brewery). Adroit Theory pours high octane, but very fascinating beers. There are beers aged in used rum barrels or whiskey barrels, Imperial Stouts, Smoked Porters, Imperial Ambers, Brown Ales..... All tasty - but beware the ABV. Continuing on Hirst, at the intersection with Hatcher Avenue, ride behind the medical center to Corcoran. They also have an expansive portfolio, but more suitable ABVs for cycling. I'm a wheat type of guy so go for the Wheatland, or try the IPL - India Pale Lager (refreshing). To return to the bike path, just continue on Hirst, past the fire station until the path and road intersect.Safe travels, and soon I will bike the wineries within biking distance of Purcellville. Cheers.
Update: I've been asked to include area bike shops available for emergency repairs. In Purcellville check out Trail's End Cycling Co and as the name suggests where the trail (sidewalk) ends. In Leesburg, Transition Triathlon is closest to the Trail with Bicycle Outfitters not too far away.
