Virginia Shenandoah National Park Hiking Tour
Misty Mountain Peaks & Cascading Waterfalls
- Available: May, June, July, August, September, October
- Activity: Level 3
- Accommodations: Comfortable Hotels
Highlights
- Hike on the Appalachian Trail right into Skyland Resort, with views of the Shenandoah River Valley
- Soak in the pools below Whiteoak and Dark Hollow Falls in Shenandoah National Park
- Discover an early 20th century presidential retreat at Rapidan Camp and other Blue Ridge Mountain history
Itinerary
Arrive in Shenandoah National Park & Hike on the Appalachian Trail
Day 1
Meet your guides and fellow hikers this morning for a short introduction and orientation at our host hotel before setting off for Shenandoah National Park. Stop for a hot drink or delicious local pastry in Sperryville, a quaint community nestled in the foothills of the park. Continue into the park and begin hiking on the Appalachian Trail, with a short detour to explore Stoney Man. As you trek toward Skyland Resort on the storied trail, take in the sprawling views of the Shenandoah River Valley and the mountains beyond. The Skyland Resort was built in 1895 on the site that would later become the highest point on Skyline Drive at 3,680 feet. Enjoy sunset views from the lodge's balconies and restaurant, daydreaming of tomorrow's adventures.
Accommodation: Skyland Resort
Activity: 5.1 miles/2-3 hours hiking with 1,444' elevation gain and 1,094' loss
Transportation: 1.5-hour private van transfer
Meals: Lunch, Dinner
Discover Dark Hollow Falls, Historic Rapidan Camp & Big Rock Falls
Day 2
Kickstart your day with breakfast at the lodge, hop in the van for a brief transfer, then hit the trail. Hike through delicate maple forest to the mossy banks and cascade of Dark Hollow Falls, the rushing water of Big Rock Falls, and historic Rapidan Camp. Once the private retreat of President Herbert Hoover and First Lady Lou Henry Hoover, Rapidan Camp was constructed in 1929. Trusted friends and advisors were hosted here, in a beautiful space perfect for outdoor adventures. After a day on the trail, unwind with time to explore the park’s historic exhibits and have dinner at Big Meadows Lodge with stunning views from the dining room.
Accommodation: Skyland Resort
Activity: 8 miles/5 hours hiking with 1,708' elevation gain and 1,878' loss
Transportation: 0.5-hour private van transfer
Meals: Breakfast, Lunch, Dinner
Summit Hawksbill Peak & Hike Whiteoak Canyon Falls
Day 3
Start the day with a delicious breakfast and watch as the fog burns away to reveal spectacular views of the Shenandoah Valley. Start with a short warm-up hike to Hawksbill Summit, the highest point in Shenandoah National Park at 4,050 feet. From Hawksbill Summit, traverse Skyline Drive to one of the park's most iconic hikes. Tracing a series of waterfalls that make up Whiteoak Canyon Falls, you'll cross bridges over the rocky banks of the river and stop to soak in the pools below each cascade, watching for wildlife along the way. In the afternoon you'll have the chance to tour and sample wines from one of the East Coast's oldest and largest wineries, Prince Michel Winery. Return to the Skyland Resort and discuss the next day's adventure.
Accommodation: Skyland Resort
Activity: 6.7 miles/4 hours hiking with 628' elevation gain and 3,131' loss
Transportation: 2-hour private van transfer
Meals: Breakfast, Lunch, Dinner
Take a Drive on Skyline Drive & Hike Dickey Ridge to Front Royal
Day 4
Today is your final day in Shenandoah National Park, but the adventure is far from over. After breakfast, depart Skyland for a scenic drive along one of the prettiest sections of Skyline Drive. Start today's hike near Lands Run Gap, hiking parallel with Skyline Drive on Dickey Ridge towards the entrance to Shenandoah National Park and the town of Front Royal. Take your time and relish views of the Shenandoah Valley and River, and lush meadows, before a long, gradual descent to the park's entrance. This afternoon, explore historic Front Royal, an incredibly quaint town that was a focal point during the Civil War. Return to the host hotel in Herndon for final farewells.
Activity: 8.5 miles/4-5 hours hiking with 1,114' elevation gain and 2,518' loss
Transportation: 2-hour private van transfer
Meals: Breakfast, Lunch
Why Travel With Us?
Your expert guides provide travelers with helpful hints, techniques, and hiking tips, plus knowledge on local wildlife, geology, and history.
MT Sobek's legacy of preservation and protection enables us to operate over 30 Global National Park adventures.
In just four days, hike some of the most iconic trails and hidden gems of Shenandoah National Park.
Dates & Prices
- 2025
- 2026
- Go Custom
- Inclusions
2025
Scheduled Dates
Price is per person, double occupancy in USD.
The earlier you book, the more choice of available dates you’ll have and once you book, your price is guaranteed.
- $3,355 price per person dbl occ
Optional:+$499 Single OccupancyWaitlist OnlyConfirmed
2026
Scheduled Dates
Price is per person, double occupancy in USD.
The earlier you book, the more choice of available dates you’ll have and once you book, your price is guaranteed.
- $3,195 price per person dbl occ
Optional:+$550 Single Occupancy (October)+$380 Single Supplement (May and September)Available - $3,195 price per person dbl occ
Optional:+$550 Single Occupancy (October)+$380 Single Supplement (May and September)Available - $3,195 price per person dbl occ
Optional:+$550 Single Occupancy (October)+$380 Single Supplement (May and September)Available - $3,195 price per person dbl occ
Optional:+$550 Single Occupancy (October)+$380 Single Supplement (May and September)Available - $3,595 price per person dbl occ
Optional:+$550 Single Occupancy (October)+$380 Single Supplement (May and September)Available - $3,595 price per person dbl occ
Optional:+$550 Single Occupancy (October)+$380 Single Supplement (May and September)Available
Go Custom
Create Your Very Own Adventure
Dreaming of an adventure designed exclusively for you? With insider access and decades of experience, our travel experts create custom tailored adventures that are perfect for families, couples, and large groups. MT Sobek's custom adventures are designed to our exacting standards and led by our award-winning adventure guides.
When to start planning? Earlier is always better when designing a custom trip. More time allows for better availability of preferred accommodations, guides and your desired activities. Ideally, start the conversation with us at least 6 months before you want to travel. If you are looking for a custom trip that departs within three months, chances are greatly diminished in securing requested accommodations and the best guides.
*Custom trips require a 25% non-refundable deposit once an itinerary is agreed upon.
Start PlanningInclusions
Price Includes
- Expertise and services of our experienced adventure guides
- All accommodations as noted in the itinerary
- All breakfasts, almost all lunches and dinners as noted in the itinerary
- Snacks and water between meals
- Additional regional guides and experts on many trips
- Comprehensive Trip Planner with detailed pre-trip information
- All fees for events, activities, or attractions fees as noted in the itinerary
- All gratuities for hotels, included meals, and activities
- Equipment and experienced guides for activities as described in the itinerary
- Park and other entry fees (unless otherwise noted)
- Transportation from trip start to end as noted in the itinerary
- Baggage transfers and porterage unless otherwise noted in the itinerary
- Group first aid kit and emergency communication device
Price Does Not Include
- Airfare or other transportation to and from trip start and end location, associated taxes, and excess baggage fees
- Alcoholic beverages
- Pre- and post-trip accommodation
- Gratuities for MT Sobek guides and guide-drivers
- Any meals on your own as noted in the itinerary
- Travel Protection Program
- Personal expenses
Need help picking your next adventure? Call us to answer your questions.
Your Guides
The best people to immerse you in a destination are the ones who live there, which is why we feature local Adventure Guides on our trips. Here are a few that you might meet on this adventure.
Ansley S.
Ansley grew up in the city of Atlanta and spent weekends and holidays in the southern Appalachian mountains. After college she worked in Wilderness Therapy in the North Carolina mountains with troubled youth. In the winters, Ansley goes out west to Utah to ski. She has hiked all around the United States, but the Smoky Mountains always call her back. Her favorite activities include, rock climbing, whitewater kayaking, rafting, scuba diving, yoga, canyoneering, skiing and, of course, backpacking.
Jack L.
Jack Lloyd was raised in Shelby, North Carolina. He grew up playing in creeks and chasing critters in the foothills of Western North Carolina. Before coming to A Walk in the Woods, Jack was a head guide for the Nantahala Outdoor Center, leading ziplining trips and guiding rafts down the river. Over the winters, Jack is a ski instructor working with kids on the slopes. As an avid whitewater paddler, he loves spending hot summer days on the water. He also enjoys gardening and foraging.
China W.
China Whitmire, a Chattanooga native, spent 15 years in Chicago working in non-profit theater and higher education upon completing her undergraduate studies at the University of Chicago. In 2021, China returned to her Appalachian roots by thru-hiking the Appalachian Trail. Now, leveraging her skills, China brings a unique blend of creativity and expertise to her role as a guide. Her love of storytelling and connection with the southern Appalachian region ultimately led her to A Walk in the Woods.
Activity Level
This trip is rated activity level 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.
Learn more about activity levels here.
Activity Snapshot
Day 1
5.1 miles/2-3 hours hiking with 1,444' elevation gain and 1,094' loss
Day 2
8 miles/5 hours hiking with 1,708' elevation gain and 1,878' loss
Day 3
6.7 miles/4 hours hiking with 628' elevation gain and 3,131' loss
Day 4
8.5 miles/4-5 hours hiking with 1,114' elevation gain and 2,518' loss
*Mileage and elevation change information is approximate and may vary slightly depending on trail conditions, weather, and route adjustments, and the guide’s discretion.
Accommodations
Spend three comfortable nights in historic National Park lodges.
Weather
Daytime temperatures of 70-80F and nighttime temperatures of 50-60F.
FAQs
We recommend guests arrive in Herdon, Virgina (Washington Dulles - airport code IAD - is the closest commercial airport) the day prior to Day 1 of the itinerary due to the early pick-up time. Your guides will meet you Day 1 at 7:00am at Hampton Inn & Suites Herndon-Reston.
Shenandoah National Park is at its best in spring (April-May) and fall (September-October), when pleasant weather meets spectacular scenery - wildflowers in spring and brilliant foliage in autumn. MT Sobek’s trips are perfectly timed for these seasons, running in May, September, and October.
The standard minimum age for these trips is 18. Families with fit younger teens may consider private and custom trip options.