Hopewell Gap & Middleburg, Virginia loop
Hopewell Gap & Middleburg, Virginia loop
3.4
(13)
33
riders
02:50
65.1km
520m
Road cycling
Cycle the moderate 40.5-mile Hopewell Gap & Middleburg, Virginia loop, gaining 1705 feet with scenic horse country views.
Last updated: February 26, 2026
Waypoints
Start point
Parking
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9.49 km
Highlight • Mountain Pass
Tip by
28.9 km
Highlight • Settlement
Tip by
65.1 km
End point
Parking
Way Types & Surfaces
Way Types
46.7 km
15.9 km
2.01 km
572 m
Surfaces
58.1 km
7.00 km
< 100 m
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Elevation
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Sunday 24 May
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This route was planned by komoot.
The loop is approximately 65.1 kilometers (about 40.4 miles) and generally takes around 2 hours and 50 minutes to complete for a cyclist with good fitness. This duration can vary based on your pace and any stops you make to enjoy the scenery or explore Middleburg.
The route is primarily a road ride, featuring mostly well-paved surfaces. Cyclists can expect rolling terrain with some significant climbs, notably the Hopewell Gap section, which has a challenging 13% grade. While this specific loop focuses on paved roads, the wider Middleburg area does offer gravel options for those seeking a different experience.
This loop is generally described as a "moderate road ride" and is best suited for cyclists with good fitness. The significant elevation gain and the 13% grade at Hopewell Gap might be challenging for absolute beginners. However, experienced beginners who are comfortable with climbs could manage it.
Spring and fall are generally the best seasons for cycling this route. The weather is typically milder, and the scenery, whether blooming in spring or vibrant with fall foliage, is particularly beautiful. Summer can be enjoyable but may involve hotter temperatures, while winter can bring colder conditions and potential for ice.
Absolutely! The route offers stunning views of horse country, expansive horse estates, and glimpses of the majestic Blue Ridge Mountains. You'll pass through the charming town of Middleburg, Virginia, known for its historic buildings, unique shops, and equestrian culture. The Hopewell Gap section winds through the Bull Run Mountains, and the area also holds historical significance from the Civil War.
While there isn't one designated trailhead parking lot for the entire loop, many cyclists choose to park in or around Middleburg, Virginia. The town offers various public parking options, from which you can easily start your ride. Always check local signage for parking regulations.
As this is primarily a road cycling route, it is not suitable for dogs to accompany cyclists on the paved sections due to safety concerns with traffic. If you are looking for dog-friendly walking trails in the wider Middleburg area, you would need to research specific local parks or unpaved trails that permit dogs.
No, there are no specific permits or entrance fees required to cycle the public roads that make up the Hopewell Gap & Middleburg, Virginia loop. It is freely accessible to cyclists.
Yes, the town of Middleburg, Virginia, is a fantastic spot for refreshments. It boasts a variety of acclaimed restaurants, cafes, and unique independently owned shops where you can refuel and relax. The historic Red Fox Inn and Tavern is a notable landmark for dining.
To fully appreciate the charm of Middleburg and potentially catch a glimpse of Olympic horse jumpers in training, consider starting your ride from the town itself. This allows you to explore its unique shops and eateries before or after tackling the challenging climbs, making for a more complete experience of the area's rich equestrian culture.