Music, Arts, & Culture Itinerary

DAY 1

Start your day in historic downtown Leesburg, heart of the Leesburg Arts & Cultural District, with close to a dozen art galleries and studios within walking distance of each other. The Fine Gallery showcases contemporary art from emerging and mid-career artists; Gleedsville Art Gallery displays original paintings, prints and mixed media and Medlin Art Gallery is an established dealer showcasing original paintings, limited edition prints, etchings and engravings.

Between gallery stops, enjoy downtown Leesburg’s public art displays. The Stanley Caulkins Memorial Project is a bronze likeness of beloved World War II airman and local civic leader on a public bench on King Street. Mike Clay’s LOVEwork sculpture, made entirely from recycled bicycle parts, is at Harrison Street along the W&OD Trail. This is a good starting point for ArtSparks, a scenic “sculpture walk” in Frank Raflo Park comprising of a dozen impressive sculptures and installations by local and regional artists.

Thirsty yet? After a quick bite at downtown “beach bar” and live music venue MacDowell Brew Kitchen, make your way to Ocelot, a Sterling-based craft brewery where beers are named after song lyrics and favorite bands. Queen fans should try the Bohemian lager “Rhapsodic” and there’s a hoppy “Castle in Brooklyn” IPA titled for lines in the Beastie Boys hit Brass Monkey. Fittingly, the brewery hosts live music too.

Put the Spotify soundtrack “Songs of Loudoun” on your radio and make you way west on Route 7 and then Route 9 to 868 Estate Vineyards in Hillsboro. The winery does more than make great Chardonel and Cab Franc. Each September, the winery hosts the LoCo Musicians Festival, with proceeds going to local musicians, and hires local artists to design the labels of the prized reserve wines.

Staying in Hillsboro, pop into inventive winery-brewery Notaviva Craft Fermentations, which goes a little further to reach the right notes. The wines and beers are all named for musical themes, so you can try a “Cantabile” (songlike) Cab Franc, or an “Ode to Joy” Meritage, named for Beethoven’s 9^th Symphony. Notaviva also hosts an annual “Wine and Music Pairing Experience" where you learn to pair the right wine to the right songs. Sing it!

Head back east for a late-night gig at iconic Tally Ho Theater in Leesburg. Opened in 1931 as Leesburg’s first movie house, it’s now a live music venue featuring big name acts such as David Allen Coe and Uncle Kracker, as well as frequent retro acts and touring cover bands. You are close to dozens of restaurants for dinner and drinks.

DAY 2

Start your morning in Loudoun’s second largest town, Middleburg, at the National Sporting Library and Museum. Established in 1954, it’s the nation’s leading resource on equestrian and outdoor pursuits – angling, shooting, foxhunting, flat-racing, polo – with a world-class research library, exhibition space and equine-themed fine art gallery. A seven-foot bronze sculpture of Virginia-bred 1993 Kentucky Derby winner Sea Hero, owned by area resident Paul Mellon, stands in the courtyard.

The Byrne Gallery on Middleburg’s Washington Street has an exquisite collection of jewelry and Impressionist paintings, while the Photo Gallery in the Pink Box Visitor and Information Center displays classic black and white photographs of Middleburg high society.

Enjoy an early lunch at Salamander Middleburg a Forbes Five-Star resort set on 340 acres of rolling countryside just outside town. Owned by billionaire entrepreneur Sheila Johnson, its walls are covered with equine art and the hotel has become a cultural touchstone as main base of the star-studded Middleburg Film Festival each October, a major stop on the Oscar trail.

A short drive east, on the outskirts of Purcellville, is the Franklin Park Arts Center – Loudoun’s more bucolic answer to DC’s Kennedy Center. A large wood-built theater in the 203-acre county park, it hosts a wide range of plays, musicals, live music and big name art exhibitions, including the first exhibit of original Bob Ross paintings on the East Coast, in September 2019.

End the night at beerhall-sized BBQ temple Monk’s, which hosts frequent live music – usually country, rock or bluegrass - for loyal bourbon and brisket fans.