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Routes
Road cycling routes
United States
Virginia
Loudoun County

Leesburg

The best road cycling routes around Leesburg

4.8

(35)

2,757

riders

22

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 aโ€ฆ

Last updated: May 2, 2026

4.7

(7)

356

riders

#1.

Herndon Caboose Park โ€“ Green Lizard Cycling, Herndon loop from Village at Leesburg

49.6km

02:04

290m

290m

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

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Moderate

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

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

Easy

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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Popular around Leesburg

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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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The Washington & Old Dominion Trail and Bridal Path parallel one another as the trails run through a tunnel of green between Leesburg and Ashburn.

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The Washington & Old Dominion Trail is a converted rail line that runs for 45 miles across Northern Virginia. It runs through a number of cities and by quite a few parks, restaurants and other spots that invite you to stop for a while. It can get quite busy is some sections, so be kind to your fellow trail users.

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Zachary
June 23, 2025, Trailside Park

A little pavilion with a bench here marks the entrance to Beth Miller Park, adjacent Trailside Park. If you follow the path from the W&O, you will come to a gazebo with a nice view over the pond.

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Trailside Park features well-maintained sports fields, pleasant surroundings, modern playgrounds, and spacious picnic areas. Adjacent to the Washington and Old Dominion Trail, it's a perfect spot for family outings, with convenient access to scenic trails and recreational facilities.

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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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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 โ€“ W&OD Trail โ€” 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 โ€“ 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.

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