Day 1 – Leesburg to Staunton
Thursday is the first and longest day on the bike. It begins with final sign-ins, bike inspections, and a New Mexican style breakfast catered by Anita’s. The departure hotel is Best Western Leesburg – 726 E Market St, Leesburg, VA. We’ll take over the main streets of historic Leesburg (named after the family that produced Robert E.) for the 5 a.m. start, before turning west away from DC on the Washington & Old Dominion bike trail. We’ll see some other early birds on the trail, so best trail manners are in order.
The rollers start early, before we reach Purcellville (mile 11) and begin the day’s long southbound leg. You’ll pass stone fences and immaculate pastures on the way to Middleburg (mile 25) in the heart of horse country, where the fashionable stores and dining spots will be lit up as you ride down empty Washington Street in the early morning.
The rolling terrain leads to Warrenton (mile 46), where you’ll want to take advantage of the full services to fuel up for the miles ahead. There is a Sheetz on your right as you enter town. If you want tasty local flavor, Red Truck Bakery is on the route at the top of the hill in the historic part of town. On your left, you’ll pass within a half block of the hotel where George McClellan bid farewell to his troops after President Lincoln relieved him of his command because of his failure to pursue Lee’s army after the Union victory at Antietam. You’ll leave town on the rural roads that begin DC Randonneurs’ much-loved Old Rag 200.
The town of Brandy Station (mile 67), site of the Civil War’s largest cavalry engagement, heralds 20 miles of flat road, with views of the Blue Ridge Mountains to the west. At the end of that stretch lies the town of Rapidan (mile 87), where you’ll cross the river of the same name and return to more rolling terrain.
The first control is at Orange (mile 93). Lunch choices include a 7-11 and Mario’s Pizzeria on route, and some fast food, including another Sheetz, off route to your right. Especially if the day is hot, be sure you have adequate supplies for what lies ahead, as there are no services between Orange and Maybelline’s convenience store and sit-down deli in Dyke (mile 122). As you leave Orange, you’ll pass James Madison’s home, Montpelier, and its impressive expanse of manicured lawn.
At Somerset (mile 100), you’ll turn west and start gaining altitude as you approach the Blue Ridge. After Maybelline’s (mile 122), the climbs increase in both frequency and difficulty, and there are no services until Crozet (mile 143). Your reward will be riding on quiet roads at the foot of the Blue Ridge.
You’ll have several choices for food in Crozet (mile 143), including two cafes, the famed Crozet Pizza, and a Dairy Queen inside the BP station just before you go under the railway bridge in the center of town. After Crozet, you’ll pass an excellent farm market, Chiles Peach Market, on your left at mile 146. By now, you’ll be riding in the heat of the afternoon, so be sure you don’t pass Chiles without plenty of liquids.
You’ll soon reach the single hardest climb on the ride, the 5.5 miles to the top of Rockfish Gap (mile 155), where a meeting in 1818 attended by presidents Jefferson, Madison, and Monroe, as well as the Great Chief Justice John Marshall, selected Charlottesville as the location for the University of Virginia. There may be food trucks at the top, where the route crosses the junction of the Blue Ridge Parkway and Skyline Drive, as well as the Appalachian Trail. But if the day is hot, we’ll have a water stop somewhere on the climb itself. The descent off the mountain takes you to Waynesboro (mile 159), where you’ll pass multiple food options on your way into town.
The 20 miles after Waynesboro gradually gain elevation coasting the west flank of the Blue Ridge. They are followed by 17 miles of descent that take you most of the way to Lexington (mile 202), the southernmost point of the Mason-Dixon and home of the Virginia Military Institute, where Stonewall Jackson taught, and Washington and Lee University, where Robert E. Lee spent the post-war years as president. You’ll want to choose dinner from one of the many services there as you recompose for the last 38 miles of the day
You’ll gain altitude steadily but not too rapidly as you ride up SR 252 though the heart of the Shenandoah Valley. If you’re thirsty, keep an eye (or ear, if it’s after dark) out for the spring on your left at mile 220. You’ll descend the last ten miles into Staunton (pronounced “Stanton”) at mile 240.
In Staunton we’re going to stay at Hotel 24 and live a bit large for randonneurs. Volunteers will valet your bike and bag and provide your room key – all you have to do is recover. Dinner and breakfast will be catered by the hotel in our own private room. Dinner is chili con carne or vegetarian, a roasted tomato soup with tortellini, and a full array of beverages, including beer and wine. You can drift off to sleep knowing that the longest and hardest day is behind you, and more beauty lies ahead. Breakfast on Friday morning is breakfast sandwiches, fruit salad, yogurt and granola, and coffee, tea, and juice.
HOTEL 24 — Staunton, Virginia