Weekend Getaway to Shenandoah County, VA

A two-night stay is all it takes to feel rejuvenated. This itinerary even takes the stress out of planning the trip.

By Hope S. Philbrick

Even if you’re lucky enough to love your job and coworkers, stress happens. Traffic, deadlines, expectations (including the ones you put on yourself) add up.

It’s time to say goodbye to the pressure of angst and hello to the calming fresh mountain air and small-town pace of Shenandoah County, Virginia.

Trade responsibilities for fun, spend some quality time with a group of friends or a special someone, and relax. That’s reason enough to visit, but there’s more!

Shenandoah County is an art haven. Dazzling artistry can be found in abundance here. Expect more than a glancing treat. Recent studies have shown that art can do the brain genuine good: Enjoy art and stress levels drop as your brain’s pleasure centers start doing a happy dance.

We’ve put together an itinerary that showcases three kinds of art readily available throughout Shenandoah County: visual, culinary and natural. Escape your routine for this art-focused, fun-for-adults weekend getaway and swap gritted teeth for an easy smile.


Welcome to Shenandoah County, Virginia!

Our wide valley is hugged by three mountain ranges, lapped by the North Fork of the Shenandoah River, and blanketed by lush forests. It’s beautiful from every angle!

Check-in to  any one of Strasburg’s home rentals in the downtown area

Stroll Downtown Strasburg.

Your mission: Locate the town’s ten eye-popping murals. Thanks to the Staufferstadt Mural Project, downtown Strasburg boasts these large-scale public works of art by world-renowned muralists. All of the murals have ties to and/or are inspired by the local area. There’s a stunning variety of colors, subjects, and artistic styles.

Enjoy dinner at Box Office Brewery.

Sip local craft brews like Stauffer Stout, Pot Town Cream Ale, Signal Knob IPA, and Massanutty Brown. Order a tasting flight and it arrives in a custom-fitted movie reel, a nod to the building’s theatre history.  The food menu elevates bar fare to yummy new heights. Box Office Brewery is committed to using local ingredients and sometimes looks no farther than the nearby taps: for example the brewery’s own American Pale Ale is incorporated into the house-made beer cheese.

Alternately, you can dine at Castiglia’s Italian Restaurant, a charming restaurant offering tasty, authentic dishes from Southern Italy. Each pizza is made from scratch and tossed by hand. End your meal with indulgent tiramisu, cheesecake, or cannoli. 


Get ready for an art-filled day.

Enjoy breakfast at The Strasburg Diner.

The Strasburg Diner has a classic diner menu with breakfast specials like corned beef hash, eggs benedict and omelets made with your choice of fillings.  You can also take a quick stroll down the street to Nancy’s Coffee Bar for one of the best-brewed cups around!

Drive to Woodstock Tower.

Enjoy a scenic drive to this local icon in the George Washington & Jefferson National Forests.

Climb Woodstock Tower.

From this observation tower, built-in 1935 by the Civilian Conservation Corps, enjoy an eagle’s-eye view of Shenandoah County. Look for the beautiful seven bends in the North Fork of the Shenandoah River. Don’t forget your camera!

Drive to Downtown Woodstock.

Snap a selfie at the Woodstock LOVEwork.

Part of Virginia Tourism’s LOVEwork program, this public art was constructed by Public Works and a local quilter. The images depicting the letters hold special meaning to locals. L is the Swiss Guard, the town icon; O is a hot air balloon, a local sport; V is vines since Woodstock is a Tree City USA, and E is the Woodstock Tower. (If you post it on social media, tag the image #loveva, #discoverwoodstockva, #woodstockartstock, and/or #visitshencova.)

Stroll Downtown Woodstock.

The fourth oldest town in Virginia has a downtown packed with antique shops, boutiques, and galleries including VECCA Art Gallery which showcases works by local artists featuring paintings, pottery, jewelry, wooden bowls, photography, and more in a range of styles. Not far from there is the Shenandoah Museum of Contemporary Art, housed in the County Chamber of Commerce building downtown. You might even decide to create your own art during your visit to Woodstock, because at the Art Spot you can sit down, choose a project and make something beautiful to take home.  

Enjoy lunch.

If you favor a vibrant downtown setting, grab a bite at Woodstock Café where Chef Jose Caravalos offers daily specials and soups plus a roster of sandwiches made with all-natural uncured meats.   In addition to sandwiches and salads for lunch, they offer dinner service Thursday-Saturday using the freshest locally sourced ingredients with a seasonally changing menu.  Chef Jose’s specialty is his homemade pasta which changes regularly in accordance with what’s in season.


If you prefer a garden aesthetic, head to Woodstock Garden Café for lunch. A supporter of Virginia’s Buy Fresh Buy Local initiative, this eatery showcases several local purveyors including farms and orchards plus a coffee roaster and spice blender. Since it showcases the season’s best ingredients, the menu changes regularly, but you can count on salads, soups, sandwiches, wraps, melts, and flatbreads.

Taste local spirits.

Visit Muse Vineyards (in Woodstock, open to 8 p.m. on Saturdays) and sit back, relax with a glass of wine while gazing across spectacular vineyard views, and reflect on the art-filled day. This award-winning winery takes an old-world approach to winemaking using estate-grown fruit from French and Italian varietals.

Enjoy dinner.

If you crave pizza and beer, head to Swover Creek Farms and Kitchen & Farm Brewery, which is located on a farm in Edinburg that’s been in continuous production by the same family for over 100 years. This craft brewery uses hops grown on the farm and the pizzeria offers sausages crafted on-site using locally raised meats, including pepperoni, chorizo, andouille, and Italian.

After dinner try a round of disc golf on the expanded 18-hole disc golf course. The course has been designed and is maintained by Eric Snyder and Nathan Hughes. There are maps and a small selection of loaner discs available in the taproom. The course is open to the public every day during daylight hours and is free to all players. Unfortunately, all alcoholic beverages are permitted on the course.


Rise and shine and get ready for a day in nature.

Yesterday, you towered over Shenandoah County at Woodstock Tower. This morning, venture underground at Shenandoah Caverns, the only caverns with elevator service in the state of Virginia. A comfortable 56-degrees year-round, these spectacular caverns are filled with geological wonders and crystalline formations including stalactites, stalagmites, helictites, flowstones, straws, columns, and unusual “breakfast bacon” that has been featured in National Geographic magazine. The hour-long guided tour journeys one mile on crushed gravel paths through 17 rooms. Lighting artfully illuminates key features.

After touring the caverns, check out vintage manmade art at neighboring facilities. American Celebration on Parade exhibits historic parade floats. Main Street of Yesteryear showcases animated store window displays.

Visit the historic Meems Bottom Covered Bridge in Mount Jackson. Originally built 1892-1893, it’s a photogenic crossing over the North Fork of the Shenandoah River. Reconstructed 1976-1979 after being vandalized, it utilizes some salvaged timbers but is also reinforced with steel and concrete to safely remain open and operational.

Enjoy lunch at Southern Kitchen Restaurant.

A New Market tradition, this restaurant holds onto its old-timey diner vibe and serves long-standing favorites like burgers, soups, salads, and sandwiches but is best known for Lloyd’s fried chicken. It’s served hot and crispy with your choice of sides like fries, slaw, buttered carrots, homemade potato salad, stewed tomatoes, applesauce, and more.

Take a hike!

Shenandoah County is 26 percent National Forest, so trail options abound—there are 178 miles of trails winding through the George Washington National Forest! Choose a hiking trail that matches your fitness level and also makes sense with your drive route (both in terms of location and time schedule).

Big Schloss is a popular trail in the Wolf Gap Recreation Area that offers amazing views and is rated a moderate challenge. The 2.2-mile trail (the total hike will be 4.4 miles), climbs Mill Mountain with some steep switchbacks intermixed with some level stretches. Once at the top, you can walk across a wooden bridge to the Big Schloss boulders. Climb up to the flat rock on top for a 360-degree view of the area where Virginia and West Virginia meet.

Depart for home. Drive safe! Along the way, make plans for your next getaway to Shenandoah County.