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Mountain stream cascading over moss-covered rocks in the Blue Ridge Mountains.

Best Hikes Near Waynesboro, Virginia

Published: July 6, 2026

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Cascading waterfall surrounded by lush forest near Waynesboro, Virginia.

There’s something special about lacing up your boots and hitting the trail while on vacation. Hiking lets you slow down, breathe fresh mountain air, and take in views you simply can’t get from a car window or a hotel balcony. The area surrounding Waynesboro, Virginia offers some of the most scenic and rewarding hikes in the state, from waterfall treks to historic tunnels to Appalachian Trail day hikes. Before you head out, be sure to check out the Iris Inn’s Hiker’s Essential Package which includes granola bars, two Iris Inn water bottles, a locally crafted hiking stick, a signature string bag, sunscreen, bug spray, and a mini first aid kit. You can even add on a picnic lunch for two so you’ll have everything you need to hit the trail prepared

Key Takeaways:

  • Humpback Rocks offers a strenuous but short one-mile climb to 360-degree summit views of the Rockfish and Shenandoah Valleys, located just 15 minutes from the Iris Inn.
  • Crabtree Falls is home to the highest vertical-drop waterfall east of the Mississippi, with a paved accessible lower overlook and a more strenuous 3-mile trail to upper vistas, about 45 minutes from the Iris Inn.
  • The Blue Ridge Tunnel Trail is a unique historic hike through a former railroad tunnel, with trailheads just 10 minutes from the Iris Inn in either direction.
  • The Bear Den Mountain Hike is an easy 2.2-mile day hike on the Appalachian Trail with sweeping views of Calf Mountain and the Shenandoah Valley, about 20 minutes from the Iris Inn.

Waynesboro Blue Ridge hiking guide infographic featuring top trails and waterfalls. Save

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Everything You Need to Know to Hike Humpback Rocks

Where do I park for Humpback Rocks?

Parking is available at the Humpback Gap parking area, located at mile post 5.8 on the Blue Ridge Parkway. The lot is right at the south end of Humpback Gap, and the trailhead begins there.

How long is the hike?

The most popular route to the top is just about one mile one-way. Don’t let the short distance fool you, it’s a steep climb with roughly 700 feet of elevation gain. Plan on about one hour to reach Humpback Rocks itself, two hours if you continue on to Humpback Mountain, and up to four hours if you make your way all the way to the Humpback Rocks picnic area.

What are the highlights?

The reward at the top is well worth the climb: 360-degree views across the Rockfish and Shenandoah Valleys. The trail is marked with blue blazes (and occasionally white, where it overlaps with the Appalachian Trail), and hikers should expect some rock scrambles and the occasional downed tree along the way.

Are there bathrooms?

Yes, porta-potties are located at the parking area, just steps from the trailhead, along with at least one picnic table.

How far is it from the Iris Inn?

Humpback Rocks is approximately 15 minutes from the Iris Inn, making it one of the closest and most convenient hikes on this list.

Hiking Guide to Crabtree Falls

Where do I park for Crabtree Falls?

Crabtree Falls has both an upper and lower parking lot at the Crabtree Falls Day Use Area, located at 11581 Crabtree Falls Highway in Montebello, just off the Blue Ridge Parkway near milepost 27. The upper lot is closest to the trailhead. Note that there is a $3 per vehicle fee, and the area is open sunrise to sunset, year-round, for day use only.

How long is the hike?

The full route to the upper overlooks is about 3 miles round-trip and is considered strenuous, with steep, rocky terrain and significant elevation gain (especially on the hike back uphill). Plan for about 2.5 to 3 hours if you’re doing the full trail. However, the very first overlook is just a few hundred feet from the parking lot along a gentle, paved path, making it accessible to hikers of all ages and abilities who just want a quick, easy view.

What are the highlights?

Crabtree Falls features five major cascades that drop a combined 1,200 feet, making it the highest vertical-drop waterfall east of the Mississippi River. The trail follows Crabtree Creek through a wooded gorge, with multiple designated viewpoints along the way. Adventurous hikers can continue past the falls another 1.2 miles to Crabtree Meadows, or cross the bridge at the 1.7-mile mark for a stone viewing area with beautiful mountain vistas.

Are there bathrooms?

Yes, there are vault toilets near the trailhead.

How far is it from the Iris Inn?

Crabtree Falls is approximately 45 minutes from the Iris Inn, making it the furthest hike on this list, but well worth the drive for waterfall lovers.

Scenic waterfall flowing through a wooded hiking trail in Virginia.

Blue Ridge Tunnel Trail FAQs

Where do I park for the Blue Ridge Tunnel Trail?

This trail has two trailheads. The eastern trailhead is located at 215 Afton Depot Lane in Afton, Virginia, while the western trailhead is at 483 Three Notched Mountain Highway in Waynesboro, Virginia.

How long is the hike?

The trail runs 2.25 miles one-way between trailheads, or 4.5 miles round-trip if you hike from one end to the other and back. Most hikers complete the round trip in about 1.5 to 2.5 hours. The tunnel portion itself is 0.8 miles long.

What are the highlights?

The centerpiece of this hike is the 4,273-foot tunnel, once part of the historic Virginia Central Railroad and now transformed into a one-of-a-kind hiking experience. The eastern portion of the trail is crushed rock, while the inside of the tunnel can be slippery, so sturdy footwear is a must.

Are there bathrooms?

Yes, porta-potties are available at both trailheads.

How far is it from the Iris Inn?

Both trailheads are approximately 10 minutes from the Iris Inn.

Bear Den Mountain Hike (Appalachian Trail) FAQs

Where do I park for the Bear Den Mountain Hike?

Park at the Beagle Gap parking area on Skyline Drive, at milepost 99.3. Keep in mind there’s a $30 per vehicle fee to enter Skyline Drive.

How long is the hike?

This is a 2.2-mile hike that’s considered easy, making it a great option for hikers of all experience levels or families looking for a lighter day on the trail.

What are the highlights?

From the parking lot, cross Skyline Drive and follow the Appalachian Trail south to enjoy views of Calf Mountain, the town of Waynesboro, and the broader Shenandoah Valley.

How far is it from the Iris Inn?

The Bear Den Mountain Hike is approximately 20 minutes from the Iris Inn.

About the Author...

Portrait of a smiling man standing in front of red foliage.

Jeremy Gassen, CTA is the General Manager of Iris Inn & Cabins and Afton Mountain Vineyards. With nearly 30 years in hospitality — from boutique B&Bs to large urban hotels — he is a Certified Tourism Ambassador and a member of the Virginia Restaurant, Lodging & Tourism Association. A Blue Ridge Mountains enthusiast and avid caver, Jeremy brings deep industry knowledge and a genuine passion for this corner of Virginia to everything he shares. 

Read more about Jeremy here.

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