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Road cycling routes
United States
Virginia
Loudoun County

Leesburg

The best road cycling routes around Leesburg

4.8

(36)

2,646

riders

20

rides

Road cycling routes around Leesburg traverse a diverse landscape characterized by its proximity to the Potomac River and the foothills of the Blue Ridge Mountains. The region features a mix of paved pathways, including the extensive Washington & Old Dominion Trail, and rural roads winding through Loudoun County's countryside. Cyclists can expect varied terrain, from flat stretches along former rail lines to gentle inclines and more challenging climbs in the surrounding rural areas. This blend of natural features provides a range of experiences for road cyclists.

Best road cycling routes around Leesburg

  • The most popular road cycling route is Luck Stone Quarry Overlook – W&OD Trail — Leesburg section loop from Loudoun County High School, a 21.9 miles (35.3 km) trail that takes 1 hour 30 minutes to complete. This easy route utilizes a section of the paved Washington & Old Dominion Trail.
  • Another top favourite among local road cyclists is Goosecup Coffee Shop loop from Village at Leesburg, a moderate 46.5 miles (74.8 km) path. This route explores the rural Loudoun County countryside with significant elevation gain.
  • Local road cyclists also love the Goosecup Coffee Shop – Hillsboro Gap loop from Village at Leesburg, a 41.7 miles (67.1 km) trail leading through the rolling hills of Loudoun County, often completed in about 2 hours 52 minutes.
  • Road cycling around Leesburg is defined by its extensive paved trail network, proximity to the Potomac River, and the varied terrain of rural Loudoun County. The network offers options for different ability levels, from easy, flat sections to moderate routes with significant climbs.
  • The routes in Leesburg are highly rated by the komoot community with an average score of 4.7 stars from over 3 reviews. More than 300 road cyclists have used komoot to explore Leesburg's varied terrain.

Last updated: October 2, 2026

5.0

(2)

47

riders

#1.

W&OD Trail — Leesburg section – Goosecup Coffee Shop loop from Leesburg

24.7km

01:01

170m

170m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Tips from the Community

Garymm755
February 28, 2026, Herndon Caboose Park

Cool place to stop.

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Nice people, great snacks and beer.

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Great cycle shop with coffee, beer, snacks, energy bars,restrooms and super helpful staff. They have bike pumps available as well as a fully functioning bike servicing shop.

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This road climbs up and down the edge of Hogback Mountain just outside of Leesburg.

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Purcellville, at the end of the rail line, has great places to stop. Monk's BBQ is fantastic and easy, and if you want to simply spend more time you can take the distillery tour at the Catoctin Creek Distilling Company (makers of great rye and other spirits). They town has also kept the old downtown shopping area straight out of the 1940s, which is great to see.

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Beautiful fun town with nice places to stop and eat. A couple of gas stations with easy Gatorade if you need to top off, or places to stop and grab lunch if you have more time

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Goosecup is a coffee shop, located in Leesburg, VA. It is is a popular spot with locals and visitors alike and is known for its coffee and cozy atmosphere.

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Herndon Caboose Park is located in the heart of Herndon, VA, and is a small but historically significant park centered around a restored caboose from the Washington & Old Dominion (W&OD) Railroad. This vibrant red caboose serves as a nod to the town’s railway heritage and is a favorite spot for photos. There are a few benches and green spaces, as well as informational plaques about the area’s railroading history. Situated along the popular W&OD Trail, it’s a popular rest stop for cyclists and walkers.

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Frequently Asked Questions

How many road cycling routes are available around Leesburg?

There are over 18 road cycling routes around Leesburg, offering a diverse range of experiences. These routes are highly rated by the komoot community, with an average score of 4.7 stars.

What kind of terrain can I expect on road cycling routes in Leesburg?

Leesburg's road cycling routes feature a varied terrain. You'll find extensive paved pathways like the Washington & Old Dominion Trail, which offers flat stretches and gentle inclines. Additionally, routes extend into rural Loudoun County, characterized by rolling hills and more challenging climbs, especially towards the foothills of the Blue Ridge Mountains.

Are there any easy road cycling routes suitable for beginners in Leesburg?

Yes, Leesburg offers several easy road cycling routes. A great option is the Luck Stone Quarry Overlook – W&OD Trail — Leesburg section loop from Loudoun County High School, which is 21.9 miles long and primarily uses the paved Washington & Old Dominion Trail. Another easy route is the Goosecup Coffee Shop loop from Leesburg, a shorter 8.5-mile ride.

Where can I find more challenging road cycling routes with significant elevation gain?

For more challenging rides, explore the rural Loudoun County countryside. Routes like the Goosecup Coffee Shop loop from Village at Leesburg cover 46.5 miles with over 2,600 feet of elevation gain. Another option is the Woodburn Road Climb – Middleburg, Virginia loop from Leesburg, which is 52.1 miles long and features significant climbs.

What natural features or landmarks can I see along the road cycling routes?

Many routes offer scenic views and pass by interesting landmarks. You can visit the Luck Stone Quarry Overlook, or cycle past the historic Clarkes Gap Stone-Arch Bridge on the Washington & Old Dominion Trail. The region's proximity to the Potomac River and the foothills of the Blue Ridge Mountains also provides stunning backdrops.

Are there family-friendly paved bike trails in Leesburg?

Absolutely. The Washington & Old Dominion (W&OD) Trail is an excellent choice for families. This 45-mile paved pathway, often called the 'skinniest park in Virginia,' is accessible from multiple points in Leesburg and is suitable for all skill levels, offering a safe and scenic environment for family rides.

Can I bring my dog on the road cycling trails in Leesburg?

While the W&OD Trail is popular and generally allows leashed dogs, it's always best to check specific regulations for each trail section or park you plan to visit. Many shared-use paths and parks in Leesburg are dog-friendly, but leash laws and waste disposal rules apply.

What is the best time of year for road cycling in Leesburg?

Spring and fall generally offer the most pleasant conditions for road cycling in Leesburg, with mild temperatures and beautiful scenery. Summer can be warm and humid, while winter can bring colder temperatures and occasional snow, though many paved trails remain accessible.

Are there places to rent bikes in Leesburg?

Yes, Leesburg has local shops like Trek Bicycle and Transition Triathlon that provide gear and support, including bike rentals. Electric bike rentals are also available for those looking for an alternative way to explore the trails.

Where can I find parking for accessing the W&OD Trail in Leesburg?

The W&OD Trail has multiple access points in Leesburg, and parking is generally available at various trailheads and nearby public lots. Specific parking information can often be found on local government or park websites, or by checking detailed route maps.

Are there any cafes or pubs near the road cycling routes in Leesburg?

Leesburg's vibrant downtown and areas near the W&OD Trail offer numerous cafes, pubs, and restaurants. Many cyclists enjoy stopping at places like Goosecup Coffee Shop, which is even featured in some popular komoot routes, for a break and refreshment.

What is the Leesburg Bike Trail Network?

Beyond the W&OD Trail, Leesburg has developed its own Bike Trail Network, comprising over 10 miles of shared-use paths, bike lanes, and routes that connect to the W&OD. This network includes designated Blue and Green Trails, offering diverse experiences through the town.

Most popular routes around Leesburg

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