Middleburg, Virginia

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Middleburg, Virginia
Date Published:
December 1, 2022
Gravel Ratio:
70% G / 30% P
Difficulty Rating:
Enjoyability Rating:
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This route is brought to you by Molly Cobbs, one of our 2022 Route Ambassadors and gravel enthusiast from Sharpsburg, MD
Photo Credits: Molly Cobbs


The scenery, low-traffic, and open space on this route are hard to beat at just 50 miles from Washington, D.C.!  

Middleburg, Virginia, in Loudoun County, is a charming, small-town, Southern destination known as the nation’s horse and hunt capital. The route passes historic landmarks, rolling horse estates, and permanently preserved lands, all of which are set against the backdrop of the beautiful Blue Ridge Mountains.

In the fall, be on the lookout and consider yourself lucky if you encounter a traditional fox hunting party on horseback complete with a swirling pack of hounds!

Although this route is best in spring and fall, this is definitely a four-season route!


There are two short sections (0.3 mile and 0.6 mile, respectively) on US Highway 50.  Use caution and patience and ride the grass parallel to the shoulder, if possible.

Do this ride if you want a scenic, intermediate gravel ride through the Nation's Horse and Hunt Capital!

Other Notes:

The route starts/ends behind Middleburg's Safeway grocery store at the intersection of Pendleton and E. Marshall Streets.  On-street parking is available in downtown Middleburg (check parking signs), or you can park at the Middleburg Community Center at 300 W. Washington St.

This is an intermediate route due to rolling hills, several climbs greater than one mile in length, and a few steep/punchy pitches.  

You can ride this route in all seasons, weather permitting, but it is especially nice in the early spring before full green-up, and in the fall.  Little or no foliage allows for great views of the countryside, especially of Bull Run Mountain and the Blue Ridge Mountains.  
In the summer, expect several long shady sections as well as long exposed sections.

There are no amenities once you leave the town of Middleburg, so plan to be self-sufficient!  The Safeway grocery store (center of town) is your best option for any last minute ride snacks, drinks, restroom stops, etc.

Middleburg's Historic District is definitely worth a stroll before or after your ride! The area is less than a mile long, but it has many unique stores, including equestrian shops, one-of-a-kind boutiques, fine art galleries, restaurants and more. Stop in at the "Pink Box" - Middleburg's Visitor Center for information on events and attractions.

I recommend grabbing a delicious "Cow Puddle Cookie" for your ride at Upper Crust Bakery! (FYI- they are cash only.)
For a post ride beverage, check out Lost Barrel Brewing on the west edge of town, or any of the of the 30 local wineries in the Middleburg American Viticultural Area!

Driving Directions

Route Contributor

2022 Ambassador: Molly Cobbs

Molly grew up in central Virginia’s Blue Ridge Mountains and started mountain biking in high school.  In college, she fell in love with endurance sports, outdoor adventure, and the American west. Ultimately, a lifestyle of adventure and endurance pursuits defined her 15+ years of living all over the west and in Alaska.  

In 2018, Molly moved back east to be closer to her family and her roots.  Exploring mid-Atlantic gravel has been essential to cultivating her “sense of place” on the East Coast and rekindling the adventurous spirit of her wild western days.  

Her coolest adventure?
An 8-day ski traverse of Denali National Park supported by dogsled team.  
Her proudest accomplishment?
Finishing the Coeur d’Alene Ironman (her first Ironman) in well under 14 hours.  
Her next goal?

Finishing strong at the 2022 Gravel Race up Spruce Knob in West Virginia.  
Her day job?

U.S. Forest Service - Molly has worked in Federal land management for more than 20 years.  
Her kryptonite?
Ice cream, puppies, naps, and funky “free!” finds on the side of the road.

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