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 Holliday House Bed & Breakfast in Strasburg.

Stay in one of the oldest structures in Strasburg, built around 1761 in the Montpelier style. Enjoy warm and cozy private bed and bath rooms appointed with comfort in mind. Innkeepers Megan Mongold and Chef DQ Baxter are so welcoming that staying here feels like staying with friends.

Stroll Downtown Strasburg.

Your mission: Locate the town’s eight 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. With Chef DQ Baxter at the helm in the kitchen, the food menu elevates bar fare to yummy new heights. He’s committed to using local ingredients and sometimes looks no farther than the nearby taps: the brewery’s Valley Pike American Pale Ale is incorporated into the house-made beer cheese.

Alternately, you can schedule a private dinner at the inn, a personal chef experience that can turn any day into what tastes like a special occasion. Private dinner menus at Holliday House offer fine dining unlike anywhere else in Shenandoah County. “It’s fancier stuff, which is fun for me,” says Baxter. When the chef is having a good time, you can expect a memorable meal.

Relax at Holliday House.

As suits your mood and the weather, enjoy time lingering on the front patio chatting with your travel companion(s) or gazing up at the night stars.  When you’ve had enough, head to your guestroom to snuggle in bed with a good book or special someone until ready to sleep.


Get ready for an art-filled day.

Enjoy breakfast at Holliday House.

One perk of having an innkeeper who’s also a chef is the made-to-order breakfast each morning. The menu offers dishes that range from savory to sweet, with options like breakfast burrito, Belgian waffle, yogurt and more. All showcase local ingredients, including eggs from just down the block.

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 7East Art Gallery and Cary’s Studio which showcase works by local artists. Featured artwork includes paintings, pottery, jewelry, wooden bowls, photography, and more in a range of styles.

If you’d like to learn the history behind the town’s Swiss Guard icon, stop at The Woodstock Museum of Shenandoah County.

Enjoy lunch.

If you favor a vibrant downtown setting, grab a bite at Woodstock Café & Shoppes where Chef George Giles offers daily specials and soups plus a roster of sandwiches made with all-natural uncured meats. Local is on the menu: Eggs are sourced from Sinclair Farms in Mount Jackson and produce comes from that farm plus the on-site garden.


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.

Explore the Shenandoah County Artisan Trail.

This trail is a curated collection of artists’ studios, agri-artisan farms, art-related venues, restaurants, and points of interest that are locally owned and offer some authentic, artisan handcrafted ties to the County’s rural culture. The brochure currently lists over 75 stops, so a couple hours is not sufficient to visit every one—but you can squeeze in a few that pique your interest, whether it’s ceramics at Laughing Orange Studio, woven goods from Posey Thisisit Llama Farm, paintings and drawings at Wolfgang Neudorfer’s studio and workshop, or another option.

Drive to Strasburg.

Tour the Shenandoah Museum of Contemporary Art (#ShenMoCA).

Director and chief curator Rupert Ravens’ biennial exhibit showcases thought-provoking contemporary art in three different locations in Strasburg. A wide range of works are on display, paintings to sculptures to videos, including some interactive pieces. “I want art to be accessible, I want to create an experience,” he says, adding that he especially enjoys this show’s “funk factor.” His art is displaying and grouping other artists’ works in ways that expand the stories and offer intriguing juxtapositions. He celebrates local and chose Shenandoah County for his project thanks to its “natural beauty—the Shenandoah Valley is one of the most beautiful areas I’ve ever been to!” he says. Exhibits may change, but ShenMoCA will continually help fuel the art vibe in Strasburg with its new installations.

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.


Take your pick among the more than 40 breweries, wineries, distilleries and cideries on the Shenandoah Spirits Trail (just call ahead to confirm operating hours before driving to your selection).

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.


If Mexican-American sounds yummy, head to Cristina’s Café in Strasburg. All dishes are prepared in house and showcase locally-sourced ingredients, from the burrito with house-made chorizo to the burger of local grass-fed beef, the local greens salad to supreme quiche made with local eggs. Save room for to-die-for desserts like caramel cake with peach filling, maple bacon cheesecake, toasted coconut cake, or whatever is available when you visit.

Try Duckpin Bowling.

For some good clean evening fun, head to Shenandoah Bowling Lanes in Mount Jackson, Virginia’s oldest bowling alley. Nostalgic charm hovers over this six-lane, 1940s-era alley where pins are placed by antique mechanics, balls roll on wooden lanes and tracks, and scores are still tallied the old-fashioned way (so bring your math skills, there aren’t computers). Duckpin bowling uses smaller balls and squattier pins for a unique challenge that’s easier on your arm.

When ready to call it a night, return to Holliday House and retreat to your guestroom.


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

Enjoy breakfast at Holliday House before checking out of the inn.

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.


The best way to experience an area is to do as the locals do. Request a Visitor Guide to discover the best of Shenandoah County and begin planning your getaway today.

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