Green Circle Trail Sections

Green Circle Trail logo


Narrative below and mile markers reflect a counterclockwise path of movement on the loop trail.

Green Circle Trail Mileage Map

University Area

Mile Markers: 0.0 to 0.3

Public Parking: Jim Barnett Park (Lowery Tennis Courts), Winchester-Frederick County Visitor's Center

This section extends from the intersection of E. Jubal Early Drive and Millwood Avenue (in front of Hampton Inn) to Wilkins Lake just south of where the trail crosses over Town Run. It includes the section of trail along University Drive, the main entrance to Shenandoah University.

Town Run Linear Park

Mile Markers: 0.3 to 1.0

Public Parking: Jim Barnett Park, Winchester-Frederick County Visitor's Center or at Shawnee Springs Preserve

Town Run Phase 1

This section of the Green Circle meanders through Shenandoah University and Jim Barnett Park near the Winchester-Frederick County Visitor's Center (1400 S. Pleasant Valley Road). Restrooms are available at the Visitor’s Center near mile marker 0.3. At mile marker 0.45, there is easy access to parking, public restrooms (seasonal), and both an adventure and accessible playground available at the Christianson Familyland area of Jim Barnett Park (Note: larger picnic shelters require advanced reservation).

Spur Trail Option: Jim Barnett Park Kiwanis Parcourse

At mile marker 0.45, there is an opportunity to connect to the Kiwanis Parcourse, a one-mile looped fitness trail (Note: Grades are not ADA accessible)with 18 exercise stations of varying levels of performance including stretching, aerobic and muscle toning stations, in Jim Barnett Park. The Parcourse connects to the War Memorial Building/Active Living Recreation Center and amenities in Jim Barnett Park (outdoor pool, athletic facilities, 18-hole disc golf course, restrooms, playgrounds, picnic areas, dog park, and more). Also, the Parcourse connects a separate park entry path to East Cork Street that then connects to a bike/walk trail along the north side of East Cork Street adjacent to the Daniel Morgan Middle School.

The trail then crosses over S. Pleasant Valley Road up Hollingsworth Drive, then left on Opequon Avenue and then through the historic Shawnee Springs Preserve. This section ends at East Pall Mall Street near the CSX Railroad trestle. Explore the Shawnee Springs Preserve, site of Sheridan's Civil War Field Hospital, the City's old water works site and many environmental features.

Spur Trail Option: Shawnee Springs Trail  

At about 0.7 miles in on the trail, an alternative 0.26-mile long trail provides a more natural option in the form of a gravel trail meandering through the wooded heart of the Springs where trail users can see remnants of the City’s old waterworks settlement basins. The two trails connect up again at mile marker 1.0 on the north end so there is no need to double-back. The main trail and the spur trail are almost the same distance.

Town Run Canyon

Mile Markers: 1.0 to 1.36

Public Parking: Court Square Autopark (South Kent Street entrance/exit) or on-street parking

Town Run Linear Park Section 2

This section was completed and opened to the public on September 27, 2016. This segment extends along Town Run beginning at East Pall Mall Street and comes up out of the canyon by means of an accessible switchback up to East Cecil Street. In the future, the Trail will link pedestrians to the historic Patsy Cline House at 608 South Kent Street via the pedestrian bridge that extends over the Green Circle Trail in the area being developed as the privately-funded public park by Mr. Timothy Mellon in memory of Patsy Cline.

At the northwest, corner of E. Cecil Street and S. Kent Street, the City’s newest public park, the Ruth Jackson Memorial Park provides a resting area and interpretive signage about Ruth’s Tea Room and the role it played in Winchester’s cultural history.

Old Town Winchester

Mile Markers: 1.36 to 2.12

Public Parking: Four downtown parking garages (24/7 access), on-street parking and parking lots

Old Town Section

From East Cecil Street, the Green Circle follows existing sidewalks and grid streets (S. Kent Street, E. Clifford Street, S. Cameron Street, and E. Cork Street) through Old Town Winchester including the south half of the Loudoun Street Mall. (NOTE: Bike riding is not permitted on the pedestrian mall, so bikers can either walk their bikes in this area or follow the alternative bike route along less busy historic downtown streets.) The trail departs the pedestrian mall left at W. Boscawen Street.

Sharrows in Old Town route

Bike Route Alternative: Clifford Street and Washington Street

At mile marker 1.50, bikers who do not wish to dismount should stay on Clifford Street and follow the green bike sharrow pavement markings three blocks west to S. Washington Street, then turn right (north) three blocks to where the two trails connect again at the intersection of Washington Street and W. Boscawen Street. The main trail and the bike trail are almost the same distance.

The Old Town section of the trail highlights the beautiful historic district and its 35+ restaurants, 60+ shops and various museums. The splash pad at the south end of the pedestrian mall provides a great place for children to run around and cool off on hot summer days. Self-cleaning public restrooms ($0.25 fee) are available at the splash pad.

Spur Trail Option: Handley Half Circle

At mile marker 2.0. the Handley Half Circle Trail, which is described as an optional loop trail alternative at the end of this page, intersects the Green Circle Trail at S. Stewart Street and meanders across the beautiful John Handley High School campus.

Amherst Street Corridor

Mile Markers: 2.12 to 3.16

Public Parking: On-street parking and MSV trail parking at entrance loop opposite Wood Avenue intersection

Amherst Street Corridor

This 1.1-mile section of the Green Circle Trail travels along Amherst Street from Old Town Winchester through Glen Burnie and the Museum of the Shenandoah Valley to the Winchester Medical Center.

Spur Trail Option: Whittier Park Connector

At about 2.43 miles in on the trail, Whittier Avenue intersects Amherst Street just west of Old Town Springs, the City’s oldest public water source (small brick structure on north side of Amherst Street). Whittier Ave provides a 0.16-mile long link to Whittier Park and the Town Run Ponding Basin constructed in the 1970's to prevent flooding downtown. Much of Town Run is contained within underground pipes in this area with just an intermittent surface flow. Whittier Park provides a playground, small picnic pavilion, and large play field areas, but no restrooms.

This Amherst Street section of the trail includes a scenic stretch that extends within an easement on the Glass-Glen Burnie private property (Museum of the Shenandoah Valley) where additional springs continuously feed Town Run. 

Spur Trail Option: The Trails at the Museum of the Shenandoah Valley (MSV)  

At points about 2.30 and 2.70 in on the trail, there are trailhead connections to the publicly accessible (free) trails developed on the 214-acre Glass-Glen Burnie property, historic homesite of Winchester’s founder Co. James Wood. The eastern MSV trailhead at marker 2.38 into the wetland area is scheduled to open in 2021 along with some of the smaller interconnecting trails. The western (main) connection to the MSV trail network at marker 2.70 opened on November 25, 2020 and provides 1.8 miles of paved walking surfaces and over 1 mile of mulch-covered trails. The trails are open daily free to the public. The paved trails are ADA-accessible with smooth surfaces and have grades not exceeding 5%. Several outdoor art exhibits are located along the MSV trails along with the “Silo Skyline,” art installation located inside an old silo near the entry road to the museum. The MSV trail network includes a connection to a trailhead with a small parking area at the west end of Jefferson Street. This trailhead at the south end of the MSV property provides a convenient connection to the Handley Half Circle Trail which is described as an optional loop trail alternative at the end of this narrative.

The Trails at the MSV map

Spur Trail Options: deGrange Orchard Park Connector and Lake Trail on Medical Center Campus

At mile marker 3.16, Meadow Branch Avenue intersects Amherst Street across from the east entrance into the Winchester Medical Center. Trail walkers can access the paved trail around the pond at privately-owned deGrange Orchard Park on the medical center campus by continuing straight ahead (west) 0.16 miles on the asphalt trail to the next intersection (Campus Blvd and Westside Station Drive). To access the park, cross Amherst Street at Campus Blvd and continue up the sidewalk to where the park entrance is located on the (west) side opposite of the Medical Office I entrance.

There is also a 0.45 mile walking trail near the center of the medical center campus around a lake that is part of the Town Run tributary. The best way to access that lake trail is to proceed north on Campus Blvd to the flashing red traffic light and then turn right onto the hospital road. A trail head is located on the north side of the hospital road just past the daycare center as shown with a red arrow in the aerial image below.

aerial image of WMC pond trail

Meadow Branch Avenue

Mile Markers: 3.16 to 4.25

Public Parking: On-street parking and John Kerr Elementary School (weekends only)

Meadow Branch Avenue

From the Amherst Street Corridor trail, the Green Circle follows Meadow Branch Avenue (across from the Medical Center entrance). This segment opened on June 3, 2016 and proceeds along the east side of Meadow Branch Avenue to Buckner Drive, where the trail again follows existing sidewalks for pedestrians and makes use of bike lanes in both directions for bikers through the Meadow Branch neighborhood. Pedestrians are encouraged to switch over to the west (opposite) side of Meadow Branch Avenue at Buckner Drive since there is incomplete sidewalk on the east side. At the south end, this segment then connects to the Jubal Drive Corridor trail where it intersects with the Abrams Creek Wetlands Preserve spur trail.

Spur Trail Option: Abrams Creek Wetlands Preserve

Abrams Creek Wetlands Preserve

At mile marker 4.25, there is a spur trail that extends 0.66 miles into the western part of the City’s Abrams Creek Wetland Preserve, including an elevated boardwalk section. The 25-acre preserve is home to what was originally the first established section of the Green Circle Trail, but is now a spur of it. The Virginia Division of Natural Heritage has identified more than a dozen rare Virginia plants that grow in the Preserve. Three of these plant species live nowhere else in Virginia. The spur trail begins near where Jubal Early Drive transitions into Meadow Branch Avenue at the intersection of Handley Avenue. The spur trail terminates at the Pennypacker Springs (private property). Trail users can double back to the Green Circle main trail (1.32 miles in and out) or use the Stonehouse Court connector in the Morlyn Hills subdivision to follow Armistead Street back to Meadow Branch Avenue (1.26 mile loop) at a point about 4.08 on the Green Circle Trail.

Click here for more information about the Preserve.

Spur Trail Option: Handley Half Circle Trail

At mile marker 4.25, the Handley Half Circle Trail, which is described as an optional loop trail alternative at the end of this page, intersects the Green Circle Trail at the intersection of Meadow Branch Avenue and Handley Avenue and meanders across the beautiful John Handley High School campus.

Jubal Early Drive Corridor

Mile Markers: 4.25 to 6.06 (a.k.a. 0.0 trail origin)

New section at Jubal Early Drive

The western portions of this section, namely from mile marker 4.25 near the Handley Avenue intersection eastward to mile marker 5.24 just east of Harvest Drive intersection is fully built. Some critical links between the Harvest Drive intersection and Valley Avenue, including a bridge over Abrams Creek, were completed in June 2021. From this point eastward, pedestrians not using the alternative route along Bellview Avenue, S. Loudoun Street, and Featherbed Lane noted below, must use the sidewalk along the south side of Jubal Early Drive.

Other than the Bellview Avenue, S. Loudoun Street and Featherbed Lane alternatives, there is no alternative to 'share-the-road' on Jubal Early Drive from just west of Plaza Drive eastward for bikers at this time.

NOTE: Bikers may want to choose an interim ‘Share-the-Road’ alternative following Handley Avenue and Bellview Avenue to avoid biking on the 4-lane divided section of Jubal Early Drive that has no bike lanes and speed limits up to 40 mph.

The total trail loop distance from the origin at Millwood and Jubal early back to the origin via Jubal Early Drive is 6.06 miles.


Bikers using the interim trail along Handley Avenue and Bellview Avenue should use caution on the steep segments of Bellview Avenue between Handley Avenue and Lewis Street. The interim bike trail intersects Valley Avenue (US Rte 11) in about 0.75 miles where they can either:

  1. return to the main trail by turning right (south) 1 one block to reconnect with the trail along Jubal Early Drive or;
  2. continue east on Bellview Avenue to S. Loudoun Street and then turn south (right) onto S. Loudoun Street.

At about 1.25 miles along the interim bike trail, it reconnects with the main trail along Jubal Early Drive. Bikers wishing to avoid biking on that four-lane divided roadway can continue across the Jubal Early Drive intersection and then left onto Featherbed Lane. The share-the-road trail continues along Featherbed Lane, then straight across South Pleasant Valley Road onto Shopping Center Dr, and turn left toward Ollie's Bargain Market (along an unnamed mall roadway) and finally turn left again onto Apple Blossom Drive back to East Jubal Early Drive where it meets up with Millwood Avenue (the University Area segment in front of the Hampton Inn). The total trail distance from the origin at Millwood and Jubal Early back to the origin via the bike alternative route (Handley, Bellview, S. Loudoun, Featherbed, and the Apple Blossom Mall roads is 6.06 miles.

Spur Trail: Handley Half Circle Trail Option

Those who don’t have time or desire to do a full 6.3+ mile-long Green Circle Trail loop or don’t want to walk/bike in the busy Jubal Early Drive/S. Pleasant Valley Road area may want to consider a “half loop” option that connects at two points on the larger Green Circle Trail and traverses the beautiful John Handley High School lawn. Near mile marker 2.0, S. Stewart Street intersects W. Boscawen Street. on the west end of Old Town. S. Stewart Street provides a direct connection to the John Handley High School grounds designed by the Olmstead Brothers, internationally renowned landscape architects. The half trail utilizes some of the many pathways crisscrossing the Handley lawn around the east and south sides of the Handley Bowl (stadium) and then extends up along Jefferson Street to the intersection of Handley Avenue. The half circle trail follows Handley Avenue to the southern terminus at the intersection of Meadow Branch Avenue near mile marker 4.25. The length of the Handley Half Circle spur trail is about 1.6 miles. Together with about 2.25 miles of the main Green Circle Trail, this western half loop totals approximately 3.9 miles. 

Note: An even shorter loop option is available by connecting to the MSV trailhead located at the west end of Jefferson Street (near the City’s elevated water tower) which opened in November 2020. See description of MSV Trail network addressed earlier under the ‘Amherst Street Corridor’ as the “Spur Trail Option: The Trails at MSV.”

This Trail Sections narrative was prepared and last updated July 2021 by Winchester Planning Department Director Tim Youmans. Please report any corrections or suggested edits to