All Trips > Virginia > Shenandoah Hiking, Winery, and Sunsets Weekend Shenandoah Hiking, Winery, and Sunsets Weekend Choose your dates 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 Choose your dates 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 5 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 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 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. In Her Words Sarah N. ★★★★★ Fantastic experience. I will definitely book another adventure! Lauren and Cara are the best guides!Wendy S. ★★★★★ Went on the Boots and Roots Gatlinburg Hike. I was hesitant as I have never done anything like this before, or even traveled alone to a destination. Let me say I am so thrilled the I went! This experience was more than I could have imagined. So glad I stepped out of my comfort zone and did this. I now cannot wait to book another trip. Thank you, Explorer Chick for such a great experience!Norma S. ★★★★★ This was a wonderful trip with Explorer Chicks. The guides were experienced and took great care of our group. This was s great way to experience the beauty of Utah. I enjoyed every minute. It was well planned and so worth the cost.Thank you to our guides Katie and Christina, you're the best!Alexandria K. ★★★★★ Joined Explorer Chick for Zion and Bryce Canyon. Kirstie and Steph took amazing care of the group and made sure we had a blast. They made sure we all got epic photos of ourselves and kept us well fed. It was great to not worry about any planning: everything was taken care of.Amy M. ★★★★★ Kirstie and Katie were great on the Zion trip. Everything was planned and done well. Adjustments had to be made due to park closures, but it didn’t phase them, and figured out plan B easily. They were very knowledgeable of the area. They both went out of their way to make the best experience possible and helped you continue when you were not sure you could.Adelia K. ★★★★★ I can only speak in superlatives when describing this trip! I came home with an empowerment afterglow that would scare both bears and men. Per usual, I was worried I would be problematic, holding back the group, dragging everyone behind, and causing the rest of the group to mumble under their breath about this woman who "shouldn't be here." In my terror, I trained by walking two miles five days a week with ankle weights. I added in stair running the last month (just ten stairs up and down ten times.) While I am relieved I trained (it came in REAL handy) I couldn't have been more wrong about group dynamics. Our guides Christina and Katie created a sense of camaraderie among us, supported each of us in incredible ways that produced an experience that I suspect will not be forgotten by any of us. Our group included women in their 30's to "almost* 70 and all body types. We laughed and snorted and sang and encouraged and overcame and we all probably thought we were going to die at one point or another- BUT WE DIDN'T. If you are considering travel with Explorer Chick, just do it. Train, know what you're getting into, but push yourself to do it. You won't regret it.damara M. ★★★★★ I recently returned home from my first EC trip-Zion and Bryce Canyon. As I expected it was a FANTASTIC time! The weather wasn't the greatest- but I lived! And I used every piece of clothing/equipment that I brought! Kirstie and Christina did a great job of leading our group and pivoting when we couldn't do the narrows. They found a less traveled trail that challenged us but was do-able for all. Food was good-trail lunches and food by EC was yummy, went to 2 restaurants that were pretty good too. When I go on my next trip I will definitely take less personal snacks. You should be fine as long as you are not a picky eater. I plan on traveling 1-2 times in 2025 with EC. They make it soooo easy-show up with some base training, a good attitude, and be ready for a FANTASTIC TIME!!!Christine C. ★★★★★ My first trip with Explorer Chicks was the Virginia Wilderness Survival 101. I went solo and it was an amazing experience. This is the first time I've ever done anything like this and I'm so glad I did. Our guide, Kara, was absolutely wonderful. She was knowledgeable, well organized, and made the trip organization so easy. I loved spending time with other women who were out for an adventure. We shared stories and enjoyed being outdoors together. I can't recommend Explorer Chicks enough and can't wait for my next adventure (hopefully Yosemite Backpacking!).Jennifer L ★★★★★ This was a transformative experience. The Explorer Chick had the itinerary planned beautifully and my guides, Kirstie and Christina were also a pivotal part of the success of my trip. They both were confident and humble and had a wealth of knowledge and training that helped me trust the process and take healthy risks that I'd never taken before. They were always prepared, patient and flexible and knew exactly how to kindly manage the various personalities (and wonderful!) on our trip. The description of the trip matched the experience so there were no surprises (except for all of us having to be flexible regarding Mother Nature's weather plans). The food was excellent - no frills but exactly what we all needed and everyone on the trip expressed happiness with our meals. Before I'd decided to go on this trip I read mostly good reviews but some mediocre but non-specific ones. For a moment, they gave me pause but I decided to try it out anyway - I am so glad I did. This was a fabulous company and the trip was one I will never forget. I went knowing no one and the women on that trip, like me, were looking to explore, try new things and laugh. We had a GREAT time. I would definitely do it again.Laura H. ★★★★★ I went on the VA Wilderness Survival/Triple Crown weekend. I honestly wasn’t sure what to expect and was a little nervous but it exceeded every expectation I had. Our guide, Kara O’Dea was exceptional. She was sweet, knowledgeable and such a calming presence. If any of us got nervous about what we were going to do, she talked us through it and encouraged us in the best way. We slayed our Triple Crown, built fires and shelters, practiced knots, brushed up on our wilderness first aid, learned elbow strikes and how to get out of choke holds, played with Sunny the amazing guide dog, developed a girl crush on Dina (the woman who runs the school) and met/ hiked with some incredible women. All while retreating at the end of the night to a cozy lodge in the woods.. It was fun, hard, exhausting and inspiring. Thank you Explorer Chick Adventure Co.!Carolina S. ★★★★★ Red River Gorge Backpacking Workshop:I was looking for a trip to experience and learn more about backpacking. I can do research all day but nothing beats real life hands-on experience! Our guide was Amy, and she did an amazing job at answering all of our questions and teaching us. She made the experience feel effortless to plan, easy to arrive and have fun. The hike itself is moderate, achievable with some preparation and determination. Bonding with women of all ages who share a passion for travel and nature is always a plus! I would recommend this trip to anyone looking to get into backpacking.The views are stunning too, did not know this gem was in KY.Amanda ★★★★★ Cannot say enough wonderful things about my trip to Belize with Explorer Chick!! Wonderful activities that make you push your limits, the sense of pride in yourself is so strong. Our wonderful fearless leader Guide Jayme had our back throughout the trip & was so well organized & flexible with details. And last but definitely not least the group of fearless women that I met, adore & continue to keep in contact with! If your thinking of booking with EC, don’t wait, go for it!Jen R. ★★★★★ Take the trip! It’s an amazing time surrounded by a community of women. I’m already planning my next adventure!Robin R. ★★★★★ There are no words to really explain the outstanding trip to Uganda!There was everything from seamless planning of accommodations to transport both in air and ground. More than this, was the camaraderie that this group displayed! We supported each other , and had a complete blast!! Nicki our guide is passionate about what she does and it shows, she was fun, and is a total package leader! The hikes and trekking for the animals especially the chimpanzees and gorillas was so DAMN amazing! Had to pinch myself so many times! I was in Africa! Not just in Africa, but having my dreams come to life about seeing the beauty and all the creatures! If you are hesitating about this trip STOP. Book it. Hike in the jungle, get wet, be a dirty girl!! Live life!!Accommodations and food were unreal!Lisa B. ★★★★★ If you prefer to work really hard and spend lots of time and energy planning a trip and dealing with the headache of navigating, finding good places to eat and fun things to do all on your own then this is not for you. Now if you prefer to show up and have amazing people guide you and cover every detail so you don't have to and love every minute of it, then this is definitely for you! As a solo traveler I was warmly welcomed (with a margarita!), met some amazing women and had the adventure of a lifetime. It would not have been possible without our brilliant guides Lauren & Amanda on the Smoky Mountain Boots & Roots Hiking Trip. This being my first time I would not hesitate to book another trip. Amazing experience!! 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