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Routes
Road cycling routes
United States
Virginia
Loudoun County
Purcellville

Middleburg, Virginia loop from Round Hill

Routes
Road cycling routes
United States
Virginia
Loudoun County
Purcellville

Middleburg, Virginia loop from Round Hill

Intermediate

6

riders

Middleburg, Virginia loop from Round Hill

02:35

52.5km

560m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: September 30, 2025

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Some segments of your route comprise a surface that may not be suitable for your chosen sport.

126 m in total

Waypoints

A

Start point

Bus stop

Get Directions

1

985 m

Purcellville Train Station – Washington & Old Dominion Trailhead

Highlight • Rest Area

Trailhead of the W&OD on the Purcellville end of the trail. Lovely place to rest and to meet and chat with other cyclists.

Tip by

2

26.3 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 …

Tip by

B

52.5 km

End point

Bus stop

Way Types & Surfaces

Way Types

47.1 km

3.28 km

1.86 km

286 m

< 100 m

< 100 m

Surfaces

34.8 km

17.6 km

126 m

< 100 m

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Elevation

Elevation

Highest point (170 m)

Lowest point (90 m)

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Wednesday 29 October

13°C

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50 %

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Nearby routes

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Intermediate

30

Leesburg – Washington & Old Dominion Trail

02:10h

50.8km

310m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Intermediate

3

Berryville – Shenandoah River Ramble

03:01h

66.1km

550m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Intermediate

1

Poolesville/Barnesville loop — Point of Rocks

02:39h

58.4km

540m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Expert

Buckeystown loop — Gravel — Brunswick

03:59h

72.5km

600m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Intermediate

South Mountain loop — Brunswick

03:34h

70.5km

870m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Intermediate

4.3

313

Green Lizard Cycling, Herndon – Herndon Caboose Park loop from Ashburn

03:28h

84.6km

490m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Easy

5.0

137

Goosecup Coffee Shop loop from Round Hill

01:30h

36.3km

250m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Easy

5.0

160

Goosecup Coffee Shop loop from Leesburg

01:36h

38.0km

260m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Intermediate

120

View of Luck Stone Quarry – Goosecup Coffee Shop loop from Lansdowne

02:00h

48.4km

310m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Intermediate

4.0

271

Green Lizard Cycling, Herndon – Rock Creek Trail loop from Ashburn

04:22h

104km

550m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Easy

4.5

97

Herndon Caboose Park – Green Lizard Cycling, Herndon loop from Dulles Town Center

00:53h

21.2km

110m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Easy
Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.
Intermediate
Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.
Expert
More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.
Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.
Intermediate

4.0

93

Roadbike loop from Leesburg

04:32h

103km

890m

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