Shenandoah National Park Hiking - Lodge Based

Trip Length4 Days
Group Size4-12
Activity level
Starting from
$2,599for REI Members
$2,859 for non-members
DeparturesMay 2025-Oct 2025

Spend four days hiking the highlights and hidden gems of Shenandoah National Park while sleeping in comfort at the historic Skyland Resort. We handle the logistics so you can enjoy fully guided, point-to-point hikes.

This journey into the heart of the Blue Ridge Mountains reveals Shenandoah National Park's natural beauty, rich cultural history, and incredible vistas. Point-to-point hikes enable us to explore more fully. We summit the park's highest peak, visit President Hoover's private retreat, and cool ourselves in the spray of waterfalls. You may even catch glimpses of black bears foraging, hear the call of wild turkeys, or see salamanders plodding along in the undergrowth. Each night we dine in unique, historic lodges with views that can't be beat. After a strenuous day on the trail, nothing is better than a delicious meal and a soft bed!

By the end of this four-day trek you'll understand the history of the park's creation, appreciate the challenges of hiking in the Blue Ridge Mountains and have a newfound appreciation for this region's charm. If you're ready for this one-of-a-kind experience, join us on the trail!

The Shenandoah River provides dramatic contrast to dense lowland forests.

Trip Highlights

  • Explore beautiful Shenandoah National Park with fellow hikers and expert guides
  • Hike on the famed Appalachian Trail right into Skyland Resort
  • Visit some of the most iconic waterfalls Shenandoah has to offer
  • Stay at the historic Skyland Resort, built at the highest point of Skyline Drive
  • Discover the storied history and culture of the Blue Ridge Mountain region

Activities

This trip is rated Moderate [3]. Trip members should be capable of hiking 5-8 hours each day (up to 10 miles) with as much as 3,100' elevation gain and loss. Trails can be rough with rocky terrain and steps built into rock, there are significant elevation changes throughout each hike. All hikes fit the Moderate [3] rating with our hike down Whiteoak Canyon at the upper end at close to with 3,100' of elevation loss.

  • Hiking

What's Included

Any park or other admission fees or permits, guides; round-trip transportation from our host hotel near Dulles International Airport to all destinations visited during the trip; all meals and snacks from lunch on Day 1 through dinner on Day 4; see trip gear list for details on gear provided during this adventure.

Accommodations

Historic National Park lodge, 3 nights

Your Adventure Itinerary

Itinerary map for Shenandoah National Park Hiking - Lodge Based
Day 1

Welcome to Shenandoah National Park and hike the Appalachian Trail

Meet your guides and fellow hikers this morning for a short introduction and orientation. We load into our van and set off for Sperryville, a quaint community nestled in the foothills of Shenandoah National Park and the start of our adventure. After a quick stop to fuel up with a hot drink or delicious local pastry we continue on to the Appalachian Trail. Today's hike takes us along the Appalachian Trail which a short detour to explore Stoney Man. Hiking on the Appalachian Trail affords us sprawling views of the Shenandoah River Valley and the mountains beyond and allows us to hike directly into the Skyland Resort. The Skyland Resort was built in 1895 on the site that would later become the highest point on Skyline Drive at 3,680 feet. Sunset views from the lodge's balconies and restaurant are sure to leave a lasting impression. Lunch and Dinner included.

Hiking: 5.1 miles, Elevation gain/loss: +1,444'/-1,094'; Van transfer: 1.5 hours

Day 2

Disconnect while exploring Dark Hollow Falls, Historic Rapidan Camp, and Big Rock Falls

Kickstart your day with breakfast at the lodge, preparing to lace up your boots for another day of adventure. After a brief transfer, we hit the trail, making our way towards Dark Hollow Falls, Big Rock Falls, and historic Rapidan Camp. Rapidan Camp holds a rich history, having been constructed in 1929 by President Herbert Hoover and First Lady Lou Henry Hoover as their secluded retreat. Here, they hosted trusted friends and advisors, in a space prime for recreation. After a day on the trail we unwind with time exploring the park’s historic exhibits and dinner at Big Meadows Lodge with stunning views from the dining room. All meals included.  

Hiking: 8.0 miles; Elevation gain/loss: +1,708’/-1,878’ 

Day 3

Vibrant views of Hawksbill Peak and the tumbling falls of Whiteoak Canyon, and a rural vineyard

Start the day with a delicious breakfast and watch as the fog burns away opening to spectacular views of the Shenandoah Valley. We start with a short warm-up hike to Hawksbill Summit, the highest point in Shenandoah National Park at 4,050 feet. From Hawksbill Summit we traverse across Skyline Drive to one of Shenandoah National Park’s most iconic hikes to Whiteoak Canyon Falls, where we can hike along a series of waterfalls. We keep our eyes peeled for wildlife and soak in each new waterfall along the way. Our hike continues, taking us to the edge of Shenandoah National Park where one of our guides will whisk us away to a local vineyard. We indulge in a vineyard tour that unveils the secrets of local winemaking. We savor the region’s finest wines and enjoy the camaraderie of our fellow travelers. All meals included. 

Hiking: 6.7 miles; Elevation gain/loss: +628’/-3,131’; Van transfer: 1 hour 

Day 4

Skyline Drive and Hiking Dickey Ridge into Front Royal

Today is our final day in Shenandoah National Park, but the adventure is not over. After breakfast we depart Skyland for a scenic drive on the most iconic section of Skyline Drive. What trip to Shenandoah is complete without enjoying Skyline Drive? Our hike today starts near Lands Run Gap and has us hiking parallel with Skyline Drive on Dickey Ridge towards the entrance to Shenandoah National Park and Front Royal. Today we relish views of the Shenandoah Valley and river, lush meadows, and a long gradual descent to the park's entrance. Tonight, we have dinner in historic Front Royal, an incredibly quaint town that was a focal point during the Civil War. After dinner we return to our host hotel where we say goodbye to our guides and fellow travelers. All meals included.

Hiking: 8.5 miles, Elevation gain/loss: +1,114'/-2,518'; Van transfer: 2.5 hours

*Although we do our very best to adhere to the schedule above, the itinerary is subject to change for numerous reasons beyond our control, including weather and terrain conditions.

Itinerary map for Shenandoah National Park Hiking - Lodge Based

Gear List

The key to staying comfortable while on an active trip is layering. To get maximum comfort with minimum weight, you need versatile layers that mix and match to create the right amount of insulation, ventilation and weather protection. Try to bring only what is necessary—this will help you and the field staff.

Already booked this trip? Sign into your online traveler profile for a more detailed list of what you'll need.

REI members can shop for gently used gear online or at most REI stores. Members can also trade in pre-loved used gear online or at any REI store in exchange for REI gift card credit. Check out Re/Supply at REI to learn more.

We provide

What to pack

Contact Us

Feel free to give us a call at 1 (800) 622-2236 should you have any questions regarding the gear list. The staff at our stores and Direct Sales ( 1 (800) 426-4840 ) will also be happy to help you with gear questions. Or check out REI Expert Advice , which has great information to help you prepare for your trip.

Trip specifics may change over time. Reviews reflect the version of the trip that was active at the time the reviewer took it. Please review the itinerary as described above and call our team for any additional details.