Exploring the Shenandoah Valley of Virginia ( + Long Weekend Itinerary)

Whenever I’m lookin for a long weekend trip and to spend some time outdoors, the Shenandoah Valley in Virginia is my first choice. There’s history, hiking, delicious food, wineries, antiques, and scenic drives. If you live within a few hours of this area, it’s a great weekend getaway.

Included below is a sample itinerary of where to go and what to do in this area of Virginia. Feel free to extend your time. in some places or cut out others. Make this work for you! I’ve personally been to all of these areas at least once and plan to go back because I enjoyed them that much.


  • Drive into Shenandoah National Park using either the Swift Run Gap Entrance or the Thornton Gap Entrance. Ideally enter while you still have a few hours of light so you can enjoy the views from Skyline Drive along the way.
  • Book your stay in either the Skyland or Big Meadows lodge inside the park. These are the only two lodge options within the park aside from a few cabins further south. Both have food options and great views.
  • Grab dinner and enjoy the sunset over the mountains.


  • For a short but beautiful morning hike, check out the Stony Man Trail. This trail is less than 2 miles round trip, but has spectacular views from the end point of the valley. Try to get here early before the trail becomes busy.
  • Drive South along Skyline drive. Stop at any of the pull offs or hikes you may want to do.
  • Exit the park through the Swift Run Gap Entrance and head to Charlottesville
  • Spend your afternoon visiting a few wineries in the Charlottesville area like Blenheim, Pippin Hill, or Veritas.
  • If you are more into history and a home cooked meal than wine, check out a tour of Monticello and don’t miss Michie Tavern down the street which serves tavern style food with an 18th century charm.
  • Stay overnight in Charlottesville at the Graduate Hotel or the Oakhurst Inn. Or, if you’re up for a little drive, find an Airbnb in Wintergreen to stay overnight. You’re sure to have beautiful views from the mountain.


  • Head into downtown Staunton and grab a cup of coffee at Crucible Coffee Roasters and browse the shops and historic downtown.
  • If you’re interested in a brewery, head to Devil’s Backbone Basecamp for a beer you can enjoy in their beautiful outdoor areas.
  • Then, go south to check out Natural Bridge State Park to see this 215 ft. tall natural bridge carved out by Cedar Creek. Check out their hiking trails if you’re up for a bit of activity while you’re there.
  • Continue on to Warm Springs and The Inn at Gristmill Square which will be your lodging for the night. Check in and head to dinner (book a reservation ahead of time) at the Waterwheel Restaurant on site for a unique dining experience in a real gristmill.
  • Stay overnight in one of the unique rooms at the Mill.


  • Drive north toward Luray Caverns. This is a beautiful cave system that’s not a State or National Park. I personally hate caves, but I’ve been in quite a few and this is still the most mesmerizing I’ve ever entered. Book a ticket for your self guided tour and enjoy the path below the surface.
  • Stop in the town of Winchester and Front Royal for lunch and enjoy the small town feeling before you head home from your weekend.

Depending on where you’re visiting from, you can do this route in reverse, or adjust when and where you stay. These are just preferences based on the times I’ve visited, but I know there’s many more hikes, hotels, parks, and places to visit so go where the adventure takes you and enjoy your trip!

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