Newest Trails near Winchester, Virginia

Recommended Routes, Photos, & More

Noteworthy

IMBA EPICS
BLM Treasures
Electric MTB Friendly
Bikepacked

Rides

Top Rated
Newest

Photos

Top Rated
Newest

Family Friendly

Rides
Trails

Trails

Top Rated
Newest

Videos

Top Rated
Newest

0.1 mi 0.1 km Bypass Trail Easy Jan 16, 2026 Haymarket, VA	Easy	Haymarket, VA	Jan 16, 2026
1.7 mi 2.8 km Creekside Easy Jan 16, 2026 Haymarket, VA	Easy	Haymarket, VA	Jan 16, 2026
1.6 mi 2.6 km Ridgetop Trail Easy Jan 16, 2026 Haymarket, VA	Easy	Haymarket, VA	Jan 16, 2026
0.9 mi 1.5 km Rollercoaster Trail Easy Jan 16, 2026 Haymarket, VA	Easy	Haymarket, VA	Jan 16, 2026
1.0 mi 1.6 km Salamander Trail Intermediate Jan 6, 2026 Haymarket, VA	Intermediate	Haymarket, VA	Jan 6, 2026
0.5 mi 0.9 km Homerun Trail Intermediate/Difficult Jan 6, 2026 Haymarket, VA	Intermediate/Difficult	Haymarket, VA	Jan 6, 2026
0.5 mi 0.8 km Ramble On Easy/Intermediate Nov 13, 2025 Berkeley Springs, WV	Easy/Intermediate	Berkeley Springs, WV	Nov 13, 2025
1.9 mi 3.1 km Sidewinder Easy/Intermediate Nov 2, 2025 Green Valley, MD	Easy/Intermediate	Green Valley, MD	Nov 2, 2025
0.3 mi 0.5 km Resurrected Intermediate Jul 5, 2025 Massanutten, VA	Intermediate	Massanutten, VA	Jul 5, 2025
0.7 mi 1.1 km Pawpaw Easy/Intermediate Apr 19, 2025 Berkeley Springs, WV	Easy/Intermediate	Berkeley Springs, WV	Apr 19, 2025
1.4 mi 2.3 km Upper Giddy-Up Intermediate/Difficult Apr 4, 2025 Berkeley Springs, WV	Intermediate/Difficult	Berkeley Springs, WV	Apr 4, 2025
1.4 mi 2.2 km Dragline Easy/Intermediate Apr 1, 2025 Ohiopyle, PA	Easy/Intermediate	Ohiopyle, PA	Apr 1, 2025
1.3 mi 2.0 km Upper Boy Scout Intermediate Mar 28, 2025 Berkeley Springs, WV	Intermediate	Berkeley Springs, WV	Mar 28, 2025
1.4 mi 2.2 km Camp Harmony Trail Intermediate Mar 22, 2025 Boswell, PA	Intermediate	Boswell, PA	Mar 22, 2025
0.9 mi 1.4 km Max Karma Trail Difficult Mar 22, 2025 Boswell, PA	Difficult	Boswell, PA	Mar 22, 2025
1.3 mi 2.1 km Dips & Jumps Trail Intermediate Mar 22, 2025 Boswell, PA	Intermediate	Boswell, PA	Mar 22, 2025
1.1 mi 1.8 km Tombstone Intermediate Mar 22, 2025 Boswell, PA	Intermediate	Boswell, PA	Mar 22, 2025
1.6 mi 2.6 km Cemetery Ridge Trail Intermediate Mar 22, 2025 Boswell, PA	Intermediate	Boswell, PA	Mar 22, 2025
1.9 mi 3.1 km WizErMo Trail Intermediate Mar 22, 2025 Boswell, PA	Intermediate	Boswell, PA	Mar 22, 2025
0.7 mi 1.1 km Slagle Hill Trail Intermediate Mar 22, 2025 Boswell, PA	Intermediate	Boswell, PA	Mar 22, 2025
0.5 mi 0.8 km Rockhaven Trail Difficult Jan 12, 2025 Ellicott City, MD	Difficult	Ellicott City, MD	Jan 12, 2025
0.6 mi 1.0 km Cub Run Inner Loop Easy Jan 4, 2025 Centreville, VA	Easy	Centreville, VA	Jan 4, 2025
0.4 mi 0.6 km River Ridge Trail Intermediate Dec 3, 2024 Ellicott City, MD	Intermediate	Ellicott City, MD	Dec 3, 2024
0.2 mi 0.4 km Return Trail (WRP Gravity) Easy Nov 13, 2024 Glenmont, MD	Easy	Glenmont, MD	Nov 13, 2024
0.2 mi 0.4 km Blue Jump Trail (WRP Gravity) Intermediate Nov 13, 2024 Glenmont, MD	Intermediate	Glenmont, MD	Nov 13, 2024
0.2 mi 0.4 km Green Trail (WRP Gravity) Easy/Intermediate Nov 13, 2024 Glenmont, MD	Easy/Intermediate	Glenmont, MD	Nov 13, 2024
0.8 mi 1.3 km Middle Giddy-Up Intermediate Nov 1, 2024 Berkeley Springs, WV	Intermediate	Berkeley Springs, WV	Nov 1, 2024
0.5 mi 0.8 km Red Pine Easy Sep 23, 2024 Ohiopyle, PA	Easy	Ohiopyle, PA	Sep 23, 2024
0.4 mi 0.7 km Greenbrier Trail Easy/Intermediate Sep 23, 2024 Ohiopyle, PA	Easy/Intermediate	Ohiopyle, PA	Sep 23, 2024
0.2 mi 0.4 km Ride the Lightning Difficult Aug 17, 2024 Berkeley Springs, WV	Difficult	Berkeley Springs, WV	Aug 17, 2024