The Insiders’ Guide to Hiking Wintergreen

Recommended loops, unique fun trails, unforgettable vistas,
and longer hikes created by connected trails

Which path to take? It can be fun to just pick what looks like a fun trail and start wandering, with a map, from there.

Wintergreen has over 30 miles of hiking trails on both the mountain and in the valley. It’s rare to find a trail here that does not connect to another of the trails that connect again to other trails.

Listed here are several proven and highly rated Wintergreen hikes locals tell their friends and family about.

Stoney Creek Park’s wide cascading stream that rolls down Wintergreen mountain from Shamokin Falls makes this valley walking path appealing every season. Go here to learn more about the forested linear park with a mile-plus long walking path with picnic tables and benches.

Hiking trails difficulty ratings:

🟢 EASY: Generally level terrain, all abilities.
🟦 MODERATE: Varied terrain, short steep sections.
DIFFICULT: Lengthy steep sections, rocky, possible water crossings.
◆◆ MOST DIFFICULT: Steep rocky sections, experienced hikers only.

Special THANKS to The Nature Foundation at Wintergreen (TNFW) - whose volunteers and staff maintain Wintergreen’s trails!

Guided hikes are offered by the Nature Foundation at Wintergreen on most Saturdays, with additional hikes during the fall and summer. Go HERE for the calendar of events.

Membership in TNFW help maintain the trails and preserve the area for years to come. Please consider becoming a member. Go HERE for membership.

You hike at your own risk

While Wintergreen is a resort community, know that most all of the mountain and valley trails here–like most trails in the Blue Ridge Mountains–insist on being taken seriously.

Follow this advice of experienced hikers of the Blue Ridge Mountains:

  • Do not hike alone.

  • Wear proper attire, including sturdy footwear.

  • Do not underestimate the terrain.

  • Carry drinking water and a snack.

  • Be aware of wildlife and respect its space.

  • Carry a hiking map.

  • Stay on marked trails to reduce your exposure to ticks and poison ivy.

  • Be aware of your limitations.

  • Know that the weather can change rapidly. Weather is different in the mountains.

Most of the trails here are open in winter, but snow and ice can make any trail treacherous. You hike at your own risk!

Trails that cross Wintergreen’s ski slopes are closed during skiing season (i.e., Loggers Alley, Cedar Cliff North).

Also see four famous hiking trails near Wintergreen.