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)NameThis field is for validation purposes and should be left unchanged. In Her Words 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!!Dawn Julian M. ★★★★★ I just got back from the Moab/Arches trip, and wow, what a fantastic adventure! Kayla and Jess were incredible, making every moment super enjoyable. It was such a treat to just relax and soak in the experience without worrying about the details. I’m definitely booking with Explorer Chick again!Kitty F. ★★★★★ 2 day 1 night - Red River Gorge, with the best group ever! Thank you so much Jody, wonderful, knowledgeable, guide. As well as a big thank you to the amazing group of "chicks". Thank you!carrie P. ★★★★★ Amazing trip!!! Lauren and Amanda were fantastic, so patient. Accomodations and food perfect....Already looking for another trip!lisa B. ★★★★★ Our Las Vegas weekend was amazing! Our guide Kara led us through our adventures like a pro! Rock climbing, amazing dinners, kayaking and overnight camping . She listened to our requests and worked with our needs. We had so much fun and made new friends - A+Deanna F. ★★★★★ What a fantastic trip! Kirstie and Hannah made everything perfect, from changing our itinerary due to weather, to making delicious lunches, snacks when needed, and taking us to experience some amazing places! I would highly recommend joining these ladies, but only if you want to have an adventure to remember! I already have another trip booked! 🙌🥾Lisa H. ★★★★★ Had the best time ever!! Got to do things I never would have dreamed of and accomplished things that I'm very proud of. Our guide Kirstie was fantastic, as was our Islandic guide/driver. Everything was planned out and taken care of so that all we (the 12 Explorer Chicks on this trip) had to think about was the next fun activity or the next great meal. I would SOOOO do another adventure with Explorer Chicks and recommend to anyone that has the desire to do something possibly out of their comfort zone. This gave me the confidence to tackle more things in the future like this.Lauren R. ★★★★★ I'm not sure there are any words to truly describe what an incredible experience I've just returned from in Iceland I had previously done a few local events with Explorer Chick, but this was my first big trip with them. I would give this 10 stars if I could! I can't believe all of the things that we fit into 1 week. Memories to last a lifetime.. ice climbing on a glacier, incredible waterfalls, driving ATVS on a black sand beach, hot springs, a beautiful and challenging hike. So many things! It was SO incredible to just show up and have everything else planned and taken care of for me. Our guide, Kirstie Mullikin, was top-notch! She went far out of her way to ensure that every single one of us had a wonderful experience. She made sure that I, with the culinary sophistication of a 5-year old, did not go hungry! This trip far exceeded any expectations I had. Looking forward to my next trip with Explorer Chick!Dr Deb S. ★★★★★ What a great experience! The trip location (Iceland) was phenomenal and the guide (Kirstie!) was the best guide one could imagine! I will travel again with Explorer Chicks, in a heartbeat an hopefully get Kirstie as guide again!! The group of ladies on this trip were diverse in their backgrounds, experience, and age but they were all out there enjoying the experience! Highly, HIGHLY recommend!!Amanda C. ★★★★★ Great experience!Casey W. ★★★★★ Savannah was a fantastic guide, and the rest of the women on our trip were great too! I was most concerned about the group dynamic as a more introverted hiker, but the atmosphere was perfect! Hoping for trips to Washington national parks in the future.Monika M. ★★★★★ I explored Arches and Canyonlands National parks solo with 6 other women and two fabulous guides, Katie and Kayla with EC. I felt immediately comfortable with our group and found it very rewarding and retreat like. We hiked, we kareoked, we laughed, and did the challenging things, it was so worth it. This company makes great lady adventures and you don’t have to lift a finger just your feet. You will not regret this trip. Loved it. 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