Goosecup Coffee Shop – Hillsboro Gap loop from Village at Leesburg

Goosecup Coffee Shop – Hillsboro Gap loop from Village at Leesburg

Moderate

4.9

(5372)

13,012

riders

Goosecup Coffee Shop – Hillsboro Gap loop from Village at Leesburg

02:55

69.3km

520m

Road cycling

Moderate 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: October 28, 2026

Waypoints

Start point

Bus stop

Get Directions

5.63 km

Leesburg Quarry (Historical Marker)

Highlight • Historical Site

The Leesburg Quarry is a historical site right off the Washington & Old Dominion Trail. This paved multi-use trail is about 45 miles and is a great way to ride …

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6.23 km

Goosecup Coffee Shop

Highlight • Cafe

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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15.0 km

Stretch of Washington & Old Dominion Trail

Highlight (Segment) • Cycleway

The stretch of the W&OD from Leesburg to Purcellville (~10 miles) is by far the best section.

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23.4 km

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.

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36.5 km

Formed by the North Fork of Catoctin Creek carving through the Short Hill Mountain, the gap creates a dramatic and scenic passage. Enjoy the rugged beauty of the cliffs, the lush greenery, and the serene flow of the creek.

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37.3 km

Historic Hillsboro at the gap of Blue Ridge

Highlight • Settlement

This intersection can be busy, since it leads directly to WV cities of Charlestown, etc close to the west. The lovely church on the north of the roundabout often has …

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56.9 km

Clarkes Gap Stone-Arch Bridge on the Washington & Old Dominion Trail

Highlight • Bridge

At 582 feet, Clarkes Gap, was the highest point on the Washington & Old Dominion Railroad. The stone bridge dates from the 1870s, but instead of a railway line now …

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