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Routes
Road cycling routes
United States
Virginia
Prince William County
Haymarket

Hopewell Gap & Middleburg, Virginia loop

Moderate

3.4

(13)

33

riders

Hopewell Gap & Middleburg, Virginia loop

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

A

Start point

Parking

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1

9.49 km

Hopewell Gap

Highlight • Mountain Pass

Hopewell Gap runs through the middle of the Bull Run Mountains. It had a strategic roll for military maneuvers during the Civil War, there was also a POW camp at …

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2

28.9 km

Middleburg, Virginia

Highlight • Settlement

The historic district of Middleburg is absolutely beautiful and offers several historic building dating back to the 1800s. There are some nice inns and shops to visit. The 'Red Fox …

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B

65.1 km

End point

Parking

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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

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

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Sunday 24 May

19°C

10°C

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This route was planned by komoot.

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Frequently Asked Questions

How long does it typically take to complete the Hopewell Gap & Middleburg, Virginia loop?

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.

What is the terrain like on this cycling route?

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.

Is this route suitable for beginner road cyclists?

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.

What are the best times of year to cycle this loop?

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.

Are there any notable landmarks or viewpoints along the way?

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.

Where can I park to access the Hopewell Gap & Middleburg, Virginia loop?

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.

Are dogs allowed on the Hopewell Gap & Middleburg, Virginia loop?

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.

Do I need any permits or pay entrance fees to cycle this route?

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.

Are there places to eat or get refreshments along the route?

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.

What's an insider tip for cycling the Hopewell Gap & Middleburg loop?

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.

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