All Trips > Virginia > Shenandoah Hiking, Winery, and Sunsets Weekend Shenandoah Hiking, Winery, and Sunsets Weekend Book Your Shenandoah Trip AT A GLANCE Virginia 10 Explorer Chicks Locally Unique Hiking, Multisport, National Park, US-Based, Weekend 3 Days 2 - Moderately Active Physical demand level for this trip Summits and Sips Photos Itinerary Logistics Activity Level What's Included Book Your Shenandoah Trip Share Summits and Sips Imagine finally treating yourself to a girls’ weekend. Only instead of sitting on someone’s living room floor fielding texts from your partner (“WHERE IS MY PRESCRIPTION NASAL SPRAY”) you’re hiking the Appalachian Trail. Eating picnics you didn’t have to pack. And tossing back Virginia wine with women who make you laugh until a you pee a little. Trade the daily hustle for mountain magic with the ultimate long weekend hiking in Shenandoah National Park. This is a more laid-back hiking adventure––active without being hardcore. We’ll explore sections of the Appalachian Trail by day, including Mary’s Rock, Whiteoak Canyon, and Hawksbill Mountain. And we’ll savor golden sunset hikes to Bearfence and Stony Man before our evening PJ parties. Our SHE-nanigan Shuttle will be conveniently parked to save us from sweary uphill climbs, whisking us away to our trailheads, an afternoon wine tasting, and our picturesque lodges with local, chef-made meals. This much beauty and sisterhood in one long weekend will feel illegal. But we promise the park rangers won’t kick us out. Photos Itinerary Expand All Days Day 1 - Mary’s Rock and Bearfence Sunset 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 Day 2 - Whiteoak Canyon and Local Winery 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 Day 3 - Hawksbill and Farewell 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. Logistics What to Pack Check out our recommended hiking gear for all trips. You’ll receive a complete packing list in your Travel Guide upon booking; note that trips may require additional specialized items. Arrival Airport City: Dulles, VA (IAD) Pick Up Location: Rendezvous Hotel Meeting Time: 7AM on Day 1 Departure Airport City: Dulles, VA (IAD) Drop Off Location: Airport and Rendezvous Hotel Return Time: 2pm. Fly out after 4pm on Day 3 Optional Add-Ons: Limited Single Room Upgrades are available at booking. You will receive a Travel Guide with all the rendezvous hotel, packing, and additional information you’ll need to prepare for your epic trip. We require a minimum of 6 Explorer Chicks for this trip. Please confirm your trip is guaranteed before booking. Activity Level Rated 2 – MODERATE ACTIVE This trip is rated a 2 – Moderate Active because of the length and frequency of hiking for all 3 days as detailed below. Although the hikes are relatively short, the terrain in Shenandoah is steep and rocky. Bearfence requires scrambling and a couple of easy climbing moves. Those with a fear of heights will be challenged. Day 1: Mary’s Rock: 5.05 miles. 1,882′ gain. Moderate. Bearfence: 1 mile. 342′ gain. Moderate. Day 2: Whiteoak Canyon: 4.8 miles. 2,500′ loss. Moderate. Stony Man: 1.5 miles. 321′ gain. Moderate Day 3: Hawksbill: 2.1 miles. 1,092′ gain. Moderate. Please consider your ability to meet the physical demands very seriously. It is for the safety and enjoyment of both you and your group. All Explorer Chicks will be required to sign an Acknowledgement of Physical Demands as part of their waiver upon booking. Read more about our Activity Levels. What's Included Lodging 1 night in a park Lodge. Shared, 2 Explorer Chicks per room. Boutique Lodge is national park owned and operated with simple twin rooms and mountain views. Has cell service and Wi-Fi. Private bath. 1 night in our second park Lodge. Shared, 2 Explorer Chicks per room. Boutique Lodge is national park owned and operated with simple twin rooms and meadow views great for night-sky viewing. Has cell service and Wi-Fi. Private bath. Activities Entrance and commercial permit fees to all National Parks and public lands Wine tasting and winery tour All activities as outlined in the itinerary Gratuities for all excursions Meals All meals as indicated in itinerary: B-2, L-3, D-2 Gratuities for included meals. Practical Professional leadership team with 2 Explorer Chick Guides A detailed Travel Guide with everything you need to know for your trip The freedom to enjoy your vacation and mindlessly wander! Not Included Rendezvous or Departure hotels Airfare Airport Transportation Alcoholic beverages Travel Insurance Meals exclusive of itineraries Costs for additional activities Gratuity for your Explorer Chick Guide (read our tipping guidelines here) 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. Let's Do This Starting From $2,099 Book Now Save $200 with our Early Bird Discounts! Just book at least 6 Months in Advance! Discount is automatically applied. Non-Refundable Deposit: $300 due at booking to secure your spot. Questions About Shenandoah? Book a call with our Destination + Guest Experience Manager, Amy, or fill out the form below. Name(Required) First Name Last Name Email(Required) Enter Email Confirm Email Send us your Shenandoah questions!(Required)EmailThis field is for validation purposes and should be left unchanged. In Her Words Book with Confidence Your wanderlust doesn’t have to wait. Our payment plans make booking your dream trip easier than ever. The best part? Zero additional fees. Payment Plans We want nothing more than for you join us. However, we understand emergencies do occur that may cause you to cancel your reservation. Cancellation Policy To protect your travel investment and your hide, we recommend purchasing travel insurance. Receive a no-hassle, online quote in less than 2 minutes. Trip Insurance Endless Wanderlust $400 off Great Smoky Mountains Hiking, Rafting and Glamping Weekend 4 DAYS, TENNESSEE Glamping, Hiking, National Park, Smoky Mountains, Weekend, White Water Rafting Glamping $400 off Moab and Arches National Parks Hiking Weekend 4 DAYS, UTAH Hiking, National Park, US-Based, Weekend Shared House $400 off Las Vegas Climbing and Paddling Weekend Adventure 4 DAYS, NEVADA Camping, Climbing, Multisport, Paddling, Water Sports Hotel, Camping $400 off Moab Hiking, Rappelling, and Off Road Weekend 4 DAYS, UTAH Canyoneering, Hiking, Multisport, National Park, Off Roading, Rappelling, US-Based, Weekend Shared House West Virginia Wild Weekend 4 DAYS, WEST VIRGINIA Camping, Multisport, National Park, US-Based, Water Sports, Weekend, White Water Rafting Camping