Ashland's Scenic Biking Routes for Winter-Weather Adventures

Snuggled amidst the frosty farmlands of Hanover County and just a snowball's throw away from Richmond, Ashland is a chill destination for local cyclists. Downtown Ashland is a perfectly positioned winter wonderland pitstop with warm restaurants, cozy coffee shops, frosty patios for gathering, and ample bike racks to hang your winter sled.

Downtown Ashland's frosty cycling routes are suitable for all levels, from snowman-making beginners to seasoned alley-cat champions. Bundle up and join rides organized by the Richmond Area Bicycling Association. Cruise on two frosty wheels, soaking in the frost-kissed charm and snow-globe-worthy architecture of Ashland's historic neighborhoods. Find all of Ashland's snow-capped cycling routes below.

Trains & Brains Route

2.2 miles

This breezy route is perfect for all ages. Start your frosty journey from the Visitors Center, pedal north along Center Street, tracking the railroad for 0.4 mile. When you hit W. Patrick Street, make a frosty left, glide over the tracks, and take an immediate snowdrift right onto a path that runs alongside the tracks for 0.5 mile, culminating at Archie Cannon Drive. Turn right onto Archie Cannon, cruise over the tracks, and then make a frost-covered right onto Henry Street.

Keep on the icy path of Henry Street for 0.4 mile and enter the shady, 116-acre campus of Randolph-Macon College. When you hit College Avenue, turn right and pedal one block to keep the winter fun rolling. You’ll see the Visitors Center on your left.

Horses & Trolleys Route
1.5, 4.6, or 5.6 miles

Tailored for young bicyclists and frosty distance riders, this route guides you through what was once a racecourse. Take a chill moment to appreciate the frosty architecture as you glide through to the Trolley Line south of Town. 

Start your frosty journey from the Visitors Center, pedaling south alongside the railroad tracks for four blocks to Stebbins Street, and make a frosty right. Glide two blocks to James Street, turn left, and continue on James for one block to Howard Street. Take a left on Howard and pedal one block to Duncan Street. Turn right on Duncan, cruise for 2 blocks to Francis Street, and pass the boyhood home of Chris Chenery - owner of Secretariat - on your right at the corner of Duncan and Race Course Streets. Make a left onto Francis and go one block to Center Street. Snow enthusiasts wanting a shorter route can cross the tracks and turn left on Center Street to sled back to the Visitors Center.

For those seeking an extra frosty adventure, turn right onto Center Street. Keep the winter magic alive, riding straight for 0.3 mile to Ashcake Road. Pedal bravely across Ashcake onto Center Street Road (Route 663). Continue for 0.9 mile to Gwathmey Church Road (Route 707). Turn left and brave the chilly railroad tracks. Continue 0.2 mile to the end of Gwathmey Church Road, passing the Trolley Line path on your left (feel free to extend this ride by 1 mile if you turn left on the Trolley Line and go 0.5 mile to the surfaced road and then turn around).

At the end of Gwathmey Church, do a frosty U-turn in front of Meriturn and pedal back to Center Street Road. Turn right and follow Center Street Road/Center Street along the tracks for 1.8 miles, savoring the winter wonder of grand homes, some dating back to the 1850s, on both sides of the tracks. Glide your way back to the Visitors Center, and may your winter ride be filled with snowy joy!

Town & Country Route

5.3 miles or 9.3 miles

Embark on this frost-kissed cycling adventure, where you'll pedal through the winter wonder of farms and pasturelands, some with a history dating back to the larger-than-life farms of the 1800s.

Start your chilly escapade at the Visitors Center, and pedal south beside the railroad tracks on Center Street to Ashcake Road (0.9 mile). Glide across Ashcake and keep the winter vibes strong as you continue straight on Center Street Road (Route 663) for 0.9 mile, reaching the intersection with Gwathmey Church Road. Turn left onto Gwathmey Church Road, and pedal through the snowy landscape for 0.5 mile to Elmont Road (Route 626). Make a frosty right onto Elmont and continue straight for 1.9 miles to Yowell Road (Route 665).

For those seeking an extra dose of winter joy, consider the Optional Extension that adds 4.0 miles. Turn left onto Yowell and pedal for 2.0 miles to Blanton Road. Revel in the winter scenery and then turn around, heading back the way you came. As you reach the intersection with Elmont, continue straight on Yowell toward town.

Turn right onto Yowell and pedal 0.4 mile to the stop sign. Continue straight like a snowstorm onto Thompson Street (Route 54), and then take the first left onto Dewey Street. Glide one block and make a frosty right onto Henry Clay Road. Pedal three blocks along Henry Clay Road, following in the snowy tracks of Henry Clay, born nearby in Hanover County in 1777. The Town of Ashland was named for Clay’s estate “Ashland” in Kentucky. Enjoy the winter breeze as you approach the railroad tracks, and there, on your right, you'll spot the Visitors Center welcoming you back from your chilly cycling odyssey.

History & Heroes Route
2.8 miles
Cycle through the chilly pages of history as you pedal along this frosty route. Kick off your snow-bike adventure at the Visitors Center and pedal south, tracing the railroad tracks like a frosty trail to the corner (½ block). Take a right turn onto Thompson Street (Route 54), then immediately veer left onto Hanover Avenue, where the town's winter tales unfold.

Glide past Ashland's town hall on the right and a restored 1926 red caboose on the left, like festive decorations on a winter sleigh. Don't forget to check out the Ashland Museum, a treasure trove of chilly artifacts. As you pedal along Hanover Avenue, a quick detour awaits you at historic Shiloh Baptist Church, founded just after the Civil War in 1866 by freed African Americans. To catch a glimpse of the current church built on land purchased in 1877, take a right turn onto S. James Street; the church is a snowball's throw away on your left.

Back on Hanover Avenue, pass Henry Clay Elementary School on the left and the Little League baseball park on the right. In 0.3 mile, you'll encounter side-by-side cemeteries on the right – Shiloh Baptist Church Cemetery (est. 1874) and Woodland Cemetery (est. 1862), both resting places with a frosty history. Woodland includes the graves of 246 Confederate soldiers and a memorial obelisk, standing tall like a winter tree.

After another 0.3 mile, Hanover Avenue transforms into a winter wonderland at Elmont Road. Turn right onto Elmont and pedal 0.5 mile to Yowell Road. Make a frosty right onto Yowell and pedal 0.4 mile to the stop sign at the intersection of Yowell and Thompson Streets. Continue straight onto Thompson Street (Route 54). Take your first left onto Dewey Street, glide one block, and turn right onto Henry Clay Road. Pedal three blocks to the railroad tracks, where you'll spot the Visitors Center on your right, like a warm haven after your chilly cycling escapade.