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 10am 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 Arrival Airport City: Dulles, VA (IAD) Pick Up Location: Rendezvous Hotel Meeting Time: 10am 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 $1999 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. 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 In Her Words Shelly B. ★★★★★ I did the 2024 Slovenia trip. My guide, Katie Klos-was awesome! And the trip was truly amazing! From the hut-to-hut hiking in the Alps- to the rest of trip adventures which included rafting, biking wine country, paddleboarding, hikes, delicious food and wine. Everything was planned and taken care of from start to finish and it was a grand adventure! It was my 3rd Explorer Chick trip and my favorite! HIghly Recommend!Kimberly S. ★★★★★ I had a wonderful experience with Explore Chicks' trip to Quito and the Galápagos Islands. Guide Mary Caperton Morton was helpful, friendly, fun, and armed with the best snacks and facts around. We hiked, snorkeled and kayaked and saw more sea turtles, sea lions and tortoises than I had dreamed possible.Aishwarya R. ★★★★★ I recently went on the Explorer chick Peru trip (multi sport adventure) in July 2024. It was an amazing trip with a lifetime worth of memorable experiences. Our guide was Ms. Christina Bruno and every travel arrangement from Cusco sight seeing, to walking tours, visiting archeological sites, river rafting, biking, MACHU Picchu hiking and rainbow mountain trek was impeccable and curated in detail. The best part of the trip was to experience the Peruvian culture including the traditional cuisine which made the experience even more fascinating. I would highly recommend this trip to many explorer chick adventurers if they are contemplating a trip to Peru.Mara K. ★★★★★ I highly recommend Explorer Chick! My trip to Red River Gorge was even better than I expected. Our guide, Jess, was AMAZING. She not only embodies the vision and mission of the company, but is also a great mentor for both amateurs and experienced trekkers. For me, this wasn't just a vacation, it was a life changing experience. I loved every minute!Christine P. ★★★★★ Our guide Kirsty was amazing! Such a great experience hiking up Half DomeShelly R. ★★★★★ Great experience. Ashley was an incredible guide.Amanda M. ★★★★★ I traveled to Alaska in June 2024 and the trip truly was the trip of a lifetime. I have done group travel before with a different group and it’s clear the guides Nicole and Kirstie truly love their jobs. They were professional and had everything planned out to the smallest detail while also being fun and encouraging the whole trip!Kim H. ★★★★★ I had an absolutely INCREDIBLE experience on a backpacking trip with Explorer Chick. Ashley was a wonderful and smart guide - perfect for beginners and backpackers that need a review. I will definitely do more trips with Explorer Chick.Megan M. ★★★★★ Explorer Chick is incredible! I just got back from an Alaska trip with Explorer Chick (June 2024) and it was one of the greatest experiences I've had. This was my second trip with a travel group, but first with EC, and there really is something so special about the female focused aspect. Our guides Kirstie and Nicole made us feel so comfortable and safe throughout every experience and fostered such a fun and warm environment. The communication prior to and during the trip was top-notch and it's clear there is an extraordinary amount of planning and thought that went into the trip and every last detail. I'm so grateful to have been able to take this trip & to meet Nicole & Kirstie and all of the girls in the group!Dana Alonso - B. ★★★★★ I recently got back from the 7 day Alaska trip and I couldn’t be happier with the time I spent there. The trip was phenomenally organized and executed by our guides Kirstie and Nicole! They were absolutely amazing keeping us informed and energized the entire trip. I loved that they also participated in ALL the activities and were so encouraging to the whole team! I definitely recommend explorer chick - they are experienced and know what they are doing! Can’t wait to book another one with them☺️Jennifer E. ★★★★★ What a wonderful trip! This is the first "blind date" girls trip i have ever taken, and I was so glad I did. I have 4 boys, and so I often forget how women support and love each other...in an entirely different way than the male sex does! Traveling with women that I have never met was a lovely experience; one that all women should experience. Mary and Kayla meshed so well as guides...they complimented each other in every way. I am a doctor with 4 grown boys, and having 2 "Moms" that dispensed sunscreen, snacks, bandaids, hand sanitizer and more to "take care of me" was beyond lovely. FINALLY- I didn't have to be the one in control!I suspect most of you reading this review are moms, with careers, and most of you probably know how difficult it is to balance different levels of ability in your kiddos, your staff, and your daily interactions. Kayla and Mary took a complex group of women with different experiences in life, different fears, and different physical capabilities and tended to each one of us as we challenged ourselves both physically and mentally. None of us felt left behind, and our fears ended up as achievements. KUDOS to both of them!Sarah W. ★★★★★ The Croatia multi-activity trip was amazing! This was my second trip through Explorer Chick and it exceeded my expectations once again. Our guide Kat was organized, knowledgeable, and engaging. Each activity was so much fun but the Via Ferrara was. by far the most exciting for me! I would recommend Explorer Chick to anyone looking to do an adventure trip.Andrea N. ★★★★★ I just returned from the Explorer Chicks Zion Park and Bryce Canyon 4 day hiking trip and I highly recommend it! It was such a treat to be able to enjoy such beautiful nature without having to think about any of the logistics. Our tour guides, Hannah and Kayla were so personable and organized. They thought of every little detail and added so many special touches that made us feel so pampered. I loved the stunning views and the challenging (but totally doable) activities during the day. The accommodations were very comfortable. I left the tour feeling rejuvenated and recharged. It was the perfect trip! Thank you Explorer Chicks for an incredible experience that I will cherish for years to come.Christine R. ★★★★★ I'd give 10 stars if that was an option. My hiking trip to Moab was an amazing experience. Guides, Mary and Steph took it levels above what I expected. I came home tired, educated and rejuvenated with 8 new amazing women friends.Samantha T. ★★★★★ A group of 6 friends joined the Zion/Bryce Hiking adventure in Utah for one friends big birthday - a first hiking trip for many of us. What a life changing adventure we had - with two incredible and thoughtful guides (Kayla and Hannah). We were blown away by the sincere thoughtfulness and consideration that our guides had for our group in addition to the outstanding experience we had in the canyon. The trip exceeded expectations and I would highly recommend Explorer Chick to anyone. Questions About Shenandoah? Name(Required) First Name Last Name Email(Required) Enter Email Confirm Email Send us your Shenandoah questions!(Required)PhoneThis field is for validation purposes and should be left unchanged. Endless Wanderlust Great Smoky Mountains Hiking, Rafting and Glamping Weekend 4 DAYS, TENNESSEE Glamping, Hiking, National Park, Smoky Mountains, Weekend, White Water Rafting Glamping Moab and Arches National Parks Hiking Weekend 4 DAYS, UTAH Hiking, National Park, US-Based, Weekend Shared House Las Vegas Climbing and Paddling Weekend Adventure 4 DAYS, NEVADA Camping, Climbing, Multisport, Paddling, Water Sports Hotel, Camping New 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