Visiting Shenandoah Valley: A Traveler’s Guide

  • Inspirations
  • on JANUARY 27, 2016
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Home to award-winning vineyards, Virginia’s Shenandoah Valley, with breathtaking mountain views and a lush, rolling basin, is the perfect weekend getaway located just off the beaten path. Cozy inns, outdoor activities, and plenty of history add to the charm of Virginia’s wine country.

Where to Stay

Image Source: Yelp

Hotel Strasburg
213 S. Holliday St.
Strasburg, VA 22657
(540) 465-9191
TripAdvisor: 4 stars, 163 reviews

Hotel Strasburg, a lovingly restored three-story Victorian structure located in downtown Strasburg, offers cozy accommodations with rooms that are each unique, decorated in period Queen Anne, Renaissance Revival, and Eastlake style antiques. In the shadow of Massanutten Mountain near the lush Shenandoah National Forest, this inn adds a palate of history to match the beauty of Shenandoah Valley’s nature.
Insider tip: Start your wine tasting adventure at the hotel in their fine dining room, where you can sample European, South American, and Australian wines.

Image Source: Yelp and Edinburg Renaissance Bed & Breakfast

Edinburg Renaissance Bed & Breakfast
212 N. Main St.
Edinburg, VA 22824
(540) 984-8286
TripAdvisor: 5 stars, 14 reviews

Just a mile off interstate 81, the Edinburg Renaissance Bed & Breakfast is centrally located in the heart of this quaint town, within walking distance of shops and eateries. Formerly a boarding house, this 1850s Victorian was restored and transformed into a bed and breakfast in 2005. Four rooms ensure a quiet stay, but look forward to friendly, personal attention from owners Bill and Donna Smith. After a long day of wine tasting and sightseeing, relax on the front porch, in the gardens, or on the patio, where the sunset pairs perfectly with a glass of wine in hand.
Insider tip: Owners Bill and Donna have seen the Shenandoah Valley change over the course of the past four decades, so be sure to ask them for their insiders’ itinerary.

Image Source: TripAdvisor and Yelp

The Widow Kip’s Country Inn
355 Orchard Dr.
Mt Jackson, VA 22842
(540) 477-2400
TripAdvisor: 4.5 stars, 55 reviews

A half mile from Mount Jackson’s cozy downtown, The Widow Kip’s Country Inn is situated on seven acres of lush land, a stone’s throw from the Shenandoah River. Accommodations in the restored 1830s homestead include rooms with fireplaces and baths, along with two cottages that make for private, romantic getaway spots. Wake up to a hearty family-style breakfast to jumpstart your wine adventure.
Insider tip: Don’t worry about boarding your pup when staying at this historic bed and breakfast: furry friends are welcome to romp in Widow Kip’s five acre fenced field.

Where to Eat

Image Source: Yelp

Southern Kitchen
9576 S. Congress St.
New Market, VA 22844
(540) 740-3514
Reservations: Not required

This neighborhood greasy spoon delivers with hospitality and home-cooked meals. Driving through New Market, it’s hard to miss—keep an eye open for the beaconing, bright neon sign. As the name implies, the kitchen whips up some fine Southern comfort food—think hotcakes, biscuits, peanut soup, and fried chicken, all served by a waitress who calls you hon.
Insider tip: While you’ll be tempted to fill up on your first course, be sure to save room for one of the daily pies.

Image Source: Yelp

Woodstock Brewhouse
123 E. Court St.
Woodstock, VA 22664
(540) 459-2739
TripAdvisor: 4.5 stars, 8 reviews
Reservations: Not required

Grab a cold one at Woodstock Brewhouse, which crafts beers like light ales and hearty stouts. Just off Woodstock’s historic Main Street, the brewery is located in a restored clothing factory with a rustic and industrial charm. A flat-bread pizza or giant Bavarian pretzel is just the trick to balance out with some carbohydrates.
Insider tip: Pitmasters 1752 Barbecue make a regular appearance at the brewery, selling succulent smoked meats and home-cooked side dishes.

Things to Do

Image Source: Facebook and Yelp

Edinburg Flea Market
164 Landfill Rd
Edinburg, VA 22824
(540) 984-8771
TripAdvisor: 4.5 stars, 5 reviews

Known for its antiquing, the Shenandoah Valley has a multitude of antique malls and shops throughout the basin. Stop at the year-round Edinburg Flea Market for a shopping spree among its 90 indoor booths. You’ll find antiques, baskets, books, collectibles, furniture, glassware, linens—the list goes on.
Insider tip: Past shoppers note it helps to visit with a plan when eyeing up vintage goods: Some days may resemble a local yard sale, but others have primo, snatched-up vintage finds like jewelry, watches, and pocket knives.


Image Source: George Washington National Forest

There are 178 miles of trails through the George Washington National Forest, so be sure to fit a little hiking into the schedule. The breathtaking views of the Shenandoah Valley and Shenandoah River are worth the trip all by themselves. In Strasburg, trekking the 4-mile Buzzard Rock North is a safe bet; In Woodstock, the Kepler Overlook Hike (6.6 miles) and Edinburg Kerns Mountain Hike (12.5 miles) are area favorites.
Insider tip: Most Shenandoah Valley hikes are beginner-friendly. Be sure to pack a pair of waterproof hiking boots, a windbreaker, and binoculars to admire Blue Ridge Mountain and Shenandoah Valley views.

Take a Scenic Drive

Image Source: Cedar Creek Battlefield

With long winding roads and a link to the past, the Shenandoah Valley is a must for history buffs. Visit Civil War sites such as Cedar Creek Battlefield in Middletown; Hupp’s Hill Civil War Park in Strasburg; Shenandoah County Historic Courthouse (the oldest working courthouse west of the Blue Ridge Mountains) in Woodstock; the old Edinburg Mill; and Our Soldiers’ Cemetery, a Confederate burial ground in Mount Jackson. Be sure to include Meems Bottom Covered Bridge in Mount Jackson on your itinerary, as it’s the longest covered bridge in Virginia, and is listed in the National Register of Historic Places.
Insider tip: After finishing your adventure at the covered bridge, head to downtown Mount Jackson to refuel with lunch at Pixie’s Cafe for a home-cooked comfort meal.

Chip Factory Visit

Image Source: Yelp

Route 11 Potato Chips
11 Edwards Way
Mt Jackson, VA 22842
(540) 477-9664
TripAdvisor: 4 stars, 118 reviews

Route 11 Potato Chips is a tasty side adventure, and it’s pretty fun to see the process of chip production at the Mount Jackson factory. This specialty potato chip producer gives facility tours Monday through Saturday from 9 a.m. to 5 p.m., and is regionally famous for flavors that range from dill pickle to Chesapeake crab. But you don’t need us to tell you to grab a snack during your visit.
Insider tip: Call ahead to make sure they will be frying chips if you are planning to take a tour of the factory—nothing beats a fresh-fried potato.

Explore the Shenandoah Caverns

Image Source: Yelp

Shenandoah Caverns
261 Caverns Rd
Quicksburg, VA 22847
(540) 477-3115
TripAdvisor: 4.5 stars, 264 reviews

An hour-long, one-mile guided tour through 17 “rooms” of these caverns will show you the beautiful breadth of and crystalline formations boasted by this geologically rich area. Halfway between Woodstock and New Market, off Interstate 81, the caverns are easy to get to, but be sure to stay after your tour to visit the other attractions. The Yellow Barn (a museum of antique carriages and farm equipment), gift shop with wine tastings, American Celebration (a display of full-size parade floats) and Main Street of Yesteryear (a display of antique department store windows) are fun for families of all ages.
Insider tip: With an elevator, the caverns are accessible for people who have difficulty walking, but still be wary of narrow passageways and uneven floors.


Image Source: DeMello Vineyards

DeMello Vineyards
2110 Quicksburg Rd.
Quicksburg, VA 22847
(540) 740-8464
Reservations: Not required

Visit this brand-new winery, located right off Interstate 81 in Quicksburg. Owners Wendy and Ed DeMello grow Petit Verdot, Cabernet Sauvignon, Cabernet Franc, Vidal Blanc, and Riesling vines on their beautiful Shenandoah estate. While sipping the different varieties on tap, admire the tasting room’s beautiful design with reclaimed wood, slate tiles, and walnut slab bar—make sure to compliment Ed, as he built the latter all by himself.
Insider tip: Wendy and Ed are new to the winery world, but are encyclopedias of oenological knowledge, so they can answer all your questions on how to break into the industry.

Image Source: The Winery at Kindred Pointe, Yelp

The Winery at Kindred Pointe
3575 Conicville Rd.
Mt Jackson, VA 22842
(540) 477-3570
TripAdvisor: 4.5 stars, 6 reviews
Reservations: Not required

Situated on 58 acres of rolling vineyard estate, this boutique winery offers tastings in its modern barn. Chardonnays range from dry and crisp with floral notes to fruit-forward and acidic varieties. Try the Malbec, as this is the first winery in the Shenandoah Valley to grow and produce its own version of this Argentinian standard.
Insider tip: The Winery at Kindred Pointe has released three new hard ciders that are only available by the glass or in a growler to go.

You may come for the wineries of Shenandoah Valley, but you’ll be quickly captivated by the rolling mountains and lush valleys that define this land. Virginia’s country setting serves as a quiet weekend getaway chock-full of history, nature, and of course, good wine.


WineCountry Collective

WineCountry is made up of a dedicated and passionate team of wine, food, and travel aficionados. We diligently explore regions, both near and far, to curate the best ideas and resources. Whether you're musing over your next wine escapade, planning a romantic weekend away, embracing the Wine Country lifestyle at home, or are simply looking to be entertained for a moment, trust us to be your comprehensive guide.