If you enjoy bookstores, old mills, and country drives, this is a splendid trip. It is a day-long excursion into scenic Western Loudoun, with a brief sojourn into rural Clarke County for a visit to a working gristmill. Stops include historic Middleburg, a wonderful bookstore and small museum in Berryville, sunset overlooking the Shenandoah Valley at Bears Den, and dinner in Purcellville.
Begin the tour from downtown Leesburg, traveling west on Loudoun Street. Just before it merges with Market Street, turn left on Dry Mill Road. Follow Dry Mill out of town as it winds its way through the countryside until it ends at Route 7 (alternately, you could follow the four-lane Route 7 to this location). Follow Business 7 west into Hamilton. Stop at Natural Mercantile as you enter Hamilton to pick up snacks for the drive. This natural food store has an extensive selection of earthy-crunchy, granola-fied goodness, along with organic chips, salsas, and juices. Stock up. If you’re ready for a stroll, Hamilton’s Main Street is just long enough to stretch your legs. Continue west on Business Route 7 through Purcellville (you’ll be back at day’s end), and turn left on 20th Street; follow this several blocks to Robey Rd. Turn left and travel past Blue Ridge Middle School, then right on Route 722, Lincoln Road, to the village of Lincoln. This picturesque little village was founded by Quakers in the 1720s and still retains an air of solitude. The many historic buildings include the Quaker meetinghouse next to the post office. Beginning at the post office, there is a 3.5 dirt road loop around town. It passes historic homes and barns and makes for a pleasing short bike ride.
Heading south from Lincoln, stay right to remain on Route 722. Just outside town, turn right onto Route 709, Chappelle Hill Road. Go straight at the junction with Route 611, then bear left to stay on Telegraph Springs Road. Follow this a few miles to Snickersville Turnpike. Turn left and follow one of the most scenic roads of the Piedmont. The little crossroads village of Philomont, with its old country store, is just ahead. To take a short detour to the Battle of Unison site, turn right on JEB Stuart Road in Philomont. Unison was the site of a significant Civil War battle in 1862. After the Battle of Antietam, Union General McClellan gave chase into Northern Virginia. General J.E.B. Stuart put up resistance in and around Unison. Vastly outnumbered, the Confederate troops held off the Union advance for three days. This gave General Longstreet time to reinforce Richmond and be in a position to defend Fredericksburg. Back in Philomont, continue driving southeast on Snickersville Turnpike, crossing over Beaverdam Creek and Goose Creek. Just west of the village of Aldie is a wayside marker on the 1862 Battle of Aldie, a four-hour fight involving mounted assaults and close fighting. At Route 50, turn left to visit Aldie, or turn right to continue on to Middleburg.