Additional Information

Gentlemen (and Gentlewomen), get ready to roll!

Following our incredible growth last year where we achieved the remarkable feat of becoming the second-largest in the nation, we're aiming for the top spot in 2025!

Join us for another unforgettable journey through the scenic beauty of Loudoun County. We'll cruise along historic byways, immerse ourselves in autumn colors, and finish in style at the Lost Barrel Brewery in Middleburg. Let's make 2025 our biggest and best drive yet!

Based on overwhelming positive feedback from last year's drive, we'll be following the same course on all-asphalt backroads, chosen for their scenic beauty and tranquil atmosphere. This route is perfect for all vehicles, especially our vintage classics that deserve a gentler pace. Once again our bretheren from the Distinguished Gentleman's Ride will accompany and shepherd us along the route on their motorcycles. 

The day begins over coffee and breakfast at the Silver Diner in Ashburn where gathering cars creates an atmosphere of anticipation and camaraderie.  Share your passion with fellow drivers and the public alike before we set off at 10:00 and embark on the first leg of our journey. Scenic Riverside Parkway guides us towards the historic heart of Old Town Leesburg, where we'll proudly parade our down iconic King Street.

The second leg leads us along the meandering Dry Mill Road, immersed in the vibrant tapestry of autumnal foliage that lines the banks of Dry Mill Branch. We'll pass through the peaceful hamlet of Hamilton before cruising through Old Town Purcellville.

Our third leg unfolds amidst the picturesque countryside of Loudoun County, where rolling horse fields and vineyards paint a beautiful scene against the sweeping background of the Blue Ridge Mountains. Snickersville Turnpike guides us through Philomont, leading to Sam Fred Road, which winds alongside the serene Wancopin Creek.

Our final stretch along Little River Turnpike culminates in a guided parade through the heart of Old Town Middleburg. We’ll finish at Lost Barrel Brewery, welcoming us with reserved parking, cozy fire pits, and inviting tables, where we'll raise a toast to a day filled with autumnal beauty, camaraderie, and the timeless allure of classic cars, all for a good cause.