15 Romantic Things to Do in Winchester VA: Finding Patsy Cline

WHY GO: Most of the things to do in Winchester VA focus on the Civil War, country music, apples, and….ghosts.

During the Civil War, the little Shenandoah Valley town of Winchester VA suffered from extreme Multiple Personality Disorder. Allegiance towards Union and Confederate forces alternated an alarming seventy two times over the course of the conflict. All this stress and anxiety may have followed the populace into the afterlife. According to some folks, Winchester is one of the most haunted towns in Virginia.

Speaking of craziness, Country Music star, Patsy Cline, drove her Winchester VA neighbors crazy with her teenage wild-girl antics.

You’ll discover all of this along with bountiful restaurants, farm markets, self guided driving tours, craft beer tasting rooms, a tiny arts village, a recently renovated historic downtown hotel, and enough history in the Winchester area to keep you busy for days.

Winchester is on our list of 20 Surprisingly Romantic Getaways in VA. Check it out if you wish to explore the state further.

Looking for someplace dreamy outside of Virginia? Check out our 150 Best Romantic Getaways in the Northeast US (Virginia to Maine).

Things to Do in Winchester VA

TOUR: Patsy Cline Historic House

For country music fans, a visit to Winchester VA wouldn’t be complete without a tour of Patsy Cline’s home.

Dirt poor, Winchester-born Virginia Hensley moved 19 times before settling in this house with her mother at age 16. She lived here from 1948 until 1957 – the longest the country music star ever lived in one place.

“Ginny,” by all accounts a “wild” girl, went on to win the Arthur Godfry Talent Scout competition in 1957. She subsequently married Gerald Cline, changed her name to Patsy, divorced Cline, and married Charlie Dick, and went on to fame and fortune before dying tragically in a plane crash in 1963 at 31 years old.

A guided tour through what was an 1840 two-room log cabin, enlarged after Cline won the $10,000 Arthur Godfry Award, is like stepping into the 1950’s. According to very knowledgeable guides, Patsy “was a product of her loving mother. Forceful, strong, they were like sisters.”

Among personal items, such as the Feed Sack pillowcases and apple-crate bedside tables, you’ll see a headshot photo signed by the famous Country Music singer. “To Mom – WE finally made it.” Check website for dates and times open – and rates. 

Patsy Cline’s Childhood Home is one of the best quirky Places to Propose in Virginia. 

VISIT: Old Courthouse Civil War Museum

Located in the Pedestrian Mall, this stately courthouse was built in 1840, and in use until 1987. Then, in 2001, it opened as a Civil War Museum. Start in the original courtroom, where the judge sat above defendants and lawyers, for a great photo op.

With original oak railings and hardwood floors, it looks the way it did in 1861 at the start of the Civil War. Due to its location close to the Northern Virginia border and with a railroad depot, Winchester was winter camp for both Union and Confederate armies.

Local allegiance whipsawed back and forth  72 times over the course of the war. In some instances within the same family, in the same house.

This “witness building” served as war-hospital, barracks and prison. Look for evidence of all three, as well as stirring exhibits, including artifacts representing the “Changing Technology of War,” “Camp Life,” and lots of bowling-ball-sized cannonballs.

Most jarring are photos of piles of amputated limbs, and original graffiti on the plaster wall where Civil War soldiers were jailed – condemning Jefferson Davis to hell. Check website for dates and times open.

VISIT: Museum of the Shenandoah Valley

Around the time Patsy Cline won the Arthur Godfry competition, Julian Wood Glass Jr.—a descendant of Winchester’s founder—inherited Glen Burnie, his ancestral home, and began a decades-long effort with his partner R. Lee Taylor to create an elegant country estate complete with formal gardens for entertaining.

Located on what is today the largest green space in the city of Winchester, the Museum of the Shenandoah Valley includes the Glen Burnie House and its surrounding gardens, a 50-000-square-foot galleries building, and a 90-acre art park with more than three miles of trails.

Permanent displays tell the Valley’s story and present objects such as quilts, folk art and furniture. In one gallery room built to look like a barn, you’ll find “Old Jake” – a fireman weathervane pot-marked by bullet holes – staring down at you beneath a ceiling made from Douglas fir trees. Furniture and fine art belonging to Glass—including a sofa once owned by England’s Queen Charlotte—is on view and traveling exhibitions are displayed in the galleries and gardens.

In fact, the formal gardens are an attraction in and of themselves, with water features and Asian flourishes. A healthy reason to get outside and wander. Check website for more information.

VISIT: Shenandoah Valley Discovery Museum

The mission of the Shenandoah Valley Discovery Museum  – “to spark curiosity and inspire learning through exploration and creative play”  – applies just as much to adults as it does to kids.

Because, who’s not a kid at heart? With three floors of interactive chances to play, this museum swarms with families on rainy days. Don’t forget the incredible rooftop – with a zany zig-zaggy tiled house.

FAMILY FARM: Fruit Hill Orchard and The Homestead Farm, Winchester

Everything in the Fruit Hill Orchard and the Homestead Farm – a country-home market – is organic and non-GMO. So Katherine Solenberger doesn’t give a whit how the very fine apples in her family’s commercial orchard look, aesthetically.

And anyway, “our apples don’t require much (organic) spraying because they’ll be processed” for juice, cider, and vinegar, rather than shipped whole to grocery stores.

Building on a three hundred year tradition – “George Washington was instrumental in planting apple orchards here” – Katherine’s great Uncle, J. Fred Thwaite, expanded the apple-growing industry in the Winchester area.

The family recently opened The Homestead Farm in Uncle Fred’s farmhouse. Go ahead, pick up organic produce and country knick-knacks.

MARKET: Richards Fruit Market, Middletown

A true family orchard and farm for 63 years, Richards Fruit Market is now run by three generations – including Mom, Mary, who at 83 years of age still puts in over 60 hours a week. You’ll find beef, apples, peaches, and a pick-your-own flower garden.

PICK YOUR OWN: Marker-Miller Orchards, Winchester VA

This market and fruit farm, Marker-Miller Orchards, offers a true hands-on harvest experience. So, pick your own apples (22 varieties from July to November), peaches, blackberries, raspberries, and other fruits to your heart’s content.

The market shop also offers a bountiful selection of produce, jams, ice cream, fudge, prepared foods. Most noteworthy are the very popular cider donuts – best eaten when just out of the oven.

VISIT: Abram’s Delight, George Washington’s Office Museum, Stonewall Jackson’s Headquarters and More Historic Sites

Stop into the Winchester Visitor Center (open daily 9-5) and you’ll be directed next door to the oldest compound in the state, “Abram’s Delight,” one of five buildings managed by the Winchester-Frederick County Historical Society. 

In 1732, when this area was an “absolute frontier,” Abe Hollingsworth called the land “a delight to behold.” A typical story of American enterprise, subsequent generations improved on the property. Soon, the family business extended into a thriving mill. Consequently, Hollingsworth built this stone home, reminiscent of his ancestral home in Cheshire, England.

The parlor features the original 1754 oak floor and iron coat-of-arms fireplace grill from the English manor. One of the small pleasures of exploring historic homes is the interesting period pieces you’ll discover. Here, the most intriguing are a “flirting fan,” with tiny mirror so that ladies could look at potential suitors without seeming forward, and a “cooling bench” – long and wide enough to lay out bodies of the deceased.

George Washington’s Office Museum

GW’s office is located in the log cabin that served as his office while supervising the construction of Fort Loudoun, features his surveying equipment and other personal effects.

Stonewall Jackson’s Headquarters

This restored Hudson River Gothic Revival house once belonged to the great-grandfather of Mary Tyler Moore, Lt. Col. Lewis T. Moore. It now serves as a museum containing hundreds of Civil War artifacts including Jackson’s prayer book and camp table. Moore provided his home to Jackson during the Confederate leader’s brief stay in Winchester during the Valley Campaign from 1861-1862.

In 1993, Mary Tyler Moore donated the reproduced gilded wallpaper that graces the walls. All properties open April – October 31: check website for hours and rates.

WALK: Old Town Pedestrian Mall

A few blocks long, chock full of boutiques and restaurants, the Old Town Pedestrian Mall is where the action is in Winchester.

Things to Do Near Winchester VA

VISIT: State Arboretum of Virginia on Blandy Experimental Farm, Boyce

You gotta love a gorgeously landscaped property with the slogan, “We don’t raise crops or cattle, we raise scientists.”

The State Arboretum of Virginia on Blandy Experimental Farm, a stunning 720-acre estate, is complete with classrooms and labs, integrating science, research, and public outreach through numerous public educational programs, a Conifer Trail (with 23 specimens), VA Birding and Wildlife Trail, one of the largest Ginkgo Groves outside of native China, and other landscapes to explore.

Sign up for a Full Moon Walk, a Make ‘n Take Air Plant Terrarium, or a Haiku Walk and Write. Bring your horse (riding trails), your dog, your kids, or just come alone for a lunchtime “TreeTorial.” Open daily dawn to dusk, free.

ARTS/SHOP: Town of Berryville

Rose Hill Barns

The arts are alive in the Lilliputian town of Berryville. So be sure to stop into Rose Hill Barns, both an Art Gallery Space and music venue, to see the latest creations, and listen to all kinds of tunes, in two repurposed dairy barns.

Then, walk through town and stop into shops like Center Ring Designs, Modern Mercantile, Fire House Gallery, and P.H. Miller Studio, owned by Peter Miller, a practitioner of the dying art of hand-crafted framing and gilding.

P.H. Miller Studio

Hailing from Woodbury/Southbury Connecticut, the internationally renowned Miller moved to Virginia to be near family. He set up his shop in Berryville, where he continues to transfer onion-skin-thin strips of gold onto hand-carved wooden frames. Come in to watch him at work – it’s fascinating.

STOP: Dinosaur Land

No, they don’t move, spit or roar, but if you’re driving towards points south, and are a fan of old-fashioned roadside kitsch, Dinosaur Land will fulfill your quirky curiosities.

About ten minutes out of Winchester in White Post, VA, original owner Joe Geraci opened the Rebel Korner Gift Shop in 1962. Then, he purchased five large dinosaur statues to attract drivers from the main road.

Over the years, the family has installed nearly fifty more in a hilly park behind the gift shop – among them a towering Cobra and mega Praying Mantis (?). OK, so it’s Dino-Snake-Insect Land, really. But it’s all in fun and a great leg stretcher.  $6 adults, $5 kids, open daily March-Dec 9:30-5 (till 6 in summer).

Best Places to Eat in Winchester VA

EAT/THROWBACK: Old Town Snow White Grill

Sit on one of the stools and watch burgers being grilled. Or, order through the window and have a seat outside. Either way, this “Home of the Slider” will warm the cockles of your non-commercial fast-food seeking heart.

EAT/BUDGET: Chop Stick Café

What this tiny corner-store eatery, the Chop Stick Cafe,  lacks in atmosphere, it more than makes up for in quality and cost. The most expensive entrees don’t inch much above $15-$18: including Pho, Sushi Rainbow Roll, and Marinated Rib Eye Stir Fry. Patrons range from tatted purple hair youngsters to suits to canoodling couples – and it’s always packed.

EAT/FINE: Violino Ristorante Italiano

The little white tablecloth Violino Ristorante Italiano I proves that Virginia can do classic Italian exceedingly well. Nibble on Zucchini Flowers and homemade pastas. Finish up with freshly made gelato.

EAT/DRINK: Village Square

Village Square is upscale American: heavy on martinis and piano-bar gatherings.

Where to Stay in Winchester VA

STAY: George Washington Hotel (Wyndam)

The venerable old George Washington Hotel built in 1924 and renovated in 2008, is just a block away from the car-free outdoor Pedestrian Mall. Gold and off white rooms were not stripped of their “pre-war” charm, with crown molding, framed full-length mirrors, Shaker-style canopy beds, double doors in suites – but of course modified to include modern amenities.

Top floor corner suites are kited out with travertine and granite bathrooms, a two-person, multi-jet, rainhead glass shower, and large tubes of True Blue Spa toiletries. The indoor pool – Greco-Roman cool – is a window away from the in-house spa and fitness room.

A beautiful lounge, just off the lobby, is dominated by a semi-circular bar and cool large-scale 20’s jazz-era mural. Even on weekday nights, it’s a popular gathering place.

STAY/TEA: Rosemont Manor, Berryville

Now a well-known wedding venue, Rosemont, built in 1811 on 315 acres, was also the site of The Battle of Berryville in September 1863. As such, it’s steeped in history. Book one of the themed rooms, named for Roosevelt, Eisenhower, Kennedy, Johnson, Nixon, Einstein and others who stayed here. It’s not just for brides and grooms.