Shenandoah Hiking, Winery, and Sunsets Weekend

Love you, D.C. but we’ve gotta drop it like it’s hot on the AT! We’ll meet at our rendezvous hotel at 7am near Dulles Airport outside of Washington, D.C. to make our way to Shenandoah National Park. It’ll be the first time we step foot on the famous Appalachian Trail as we hike our booties up to Mary’s Rock.

At the summit, you’ll be rewarded with an osprey’s view of the surrounding Shenandoah Valley and Blue Ridge Mountains. The trail descends to the peaceful Pinnacles Picnic Area where our SHE-nanigan Shuttle will be waiting to chauffeur us to our home for tonight. 

Nestled in the breathtaking beauty of Shenandoah National Park, our lodge is a front-row seat to Mother Nature’s runway show. Enjoy jaw-dropping views from the Sky Deck, the highest point along the Skyline Drive.   

In the evening, we’ll embark on a sunset hike to Bearfence and witness the landscape transform into a breathtaking golden kaleidoscope. This hike is more of a scramble where we’ll show off a climbing move or two. Those with a fear of heights may get spicy armpits, but will be rewarded with supreme views. As the sun peaces out for the night, we’ll quietly perch on an exposed rock summit to bask in the radiant glow. 

Elevation Gain: 1,882’/342’

Distance: 5 miles/1 mile

Hiking Time: 4 hours/1 hours

Transfer: 1.5 hours

Accommodations: Park Lodge

Meals: L-D

Help yourself to a civilized breakfast that isn’t coffee and emails in Skyland’s dining room. Enjoy your food while gazing out floor-to-ceiling windows that overlook the mountains. We’re booting up for one of Shenandoah’s classic hikes––Whiteoak Canyon. The trail spoils us with gorgeous waterfalls, challenging terrain, vibrant flora, and the sounds of rushing water. We’ll take a million photos of the Upper and Lower Falls and cool off in some natural swimming holes if the boobsweat gods demand it.

The loyal SHE-naningan Shuttle will be waiting for us at the bottom of the canyon––saving us from a STEEP HIKE back up the canyon. Just when you think life can’t get any better, you’ll be handed a chilled glass of rosé upon arriving at our local winery tour. Our lovely hosts will lead us through the vines and the winery barrel room, where they’ll share the saga of turning sour grapes into delicate wine. We’ll enjoy a group tasting of three or four wines, all explained in first-class fashion but without the pretentious atmosphere. We’ll pair our wine with a yummy picnic relaxing on the back patio.

Once we’re feeling warm and fuzzy, we’ll pile back into the Shuttle and check into our second lodge, a rustic retreat surrounded by expansive meadows. We’ll round out our evening with another sunset hike. The view from Stony Man softens into an otherworldly glow as the sun sets. Shenandoah twilight in the company of wonderful women might make you emotional.

Elevation Loss/Gain: -2,500’/321’

Distance: 4.8 miles/1.5 miles

Hiking Time: 3 hours/1.5 hours

Transfer: 1 hour

Accommodations: Park Lodge

Meals: B-L-D

Save those tears for after the hike! We’ll enjoy our last delicious breakfast in the Dining Hall before loading up the Shuttle. Our drive takes us to the highest mountain in the park, Hawksbill Mountain. Even though our out-and-back trek is short and sweet, it is intensely beautiful. You’ll meander through dense forests filled with deciduous and coniferous trees. As you ascend Hawksbill, the terrain transitions to rocky outcrops, offering heart-pounding sneak peeks of the surrounding valleys and ridges. Upon reaching the summit of Hawksbill, you’re treated to an eye-jiggling panorama with women who might be moved to grab your hand. New core memory, unlocked.

We’ll take the Skyline Drive back to our rendezvous hotel for final goodbyes and frantic airdropping of photos. A group airport transport is provided with a planned return to Dulles after 2pm. Let’s do this again real soon, okay? 

Elevation Loss/Gain: 498’

Distance: 2.1 miles

Hiking Time: 2 hours

Transfer: 2 hours

Meals: B-L

Explorer Chick reserves the option to modify trip itineraries at the discretion of your tour director as necessary due to weather, conditions, illness, injury, group dynamics, or other unforeseen incidents.