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.

Old Town Winchester Pedestrian Mall at Sunset
Old Town Winchester Pedestrian Mall at Sunset

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

Patsy Cline Home, Winchester VA
Patsy Cline Home, 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

Old Courthouse Civil War Museum, Winchester VA
Old Courthouse Civil War Museum, Winchester VA

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.

Civil War Prison Graffiti damning Jefferson Davis to Hell at Courthouse Museum, Winchester VA
Civil War Prison Graffiti damning Jefferson Davis to Hell at Courthouse Museum, Winchester VA

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.

Museum of the Shenandoah Valley Winchester VA

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.

Homestead Farm at Fruit Hill Orchard, Winchester VA
Homestead Farm at Fruit Hill Orchard, Winchester VA

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.

Organic heirloom tomatoes at Homestead Farm, Winchester VA
Organic heirloom tomatoes at Homestead Farm, Winchester VA

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.

Three Generations of owners at Richards Fruit Market, Middletown VA
Three Generations of owners at Richards Fruit Market, Middletown VA

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.

Marker Miller Orchards, Winchester VA

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.

Abram's Delight, Winchester VA
Abram’s Delight, Winchester VA

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, Winchester VA
George Washington’s Office Museum, Winchester VA

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.

Old Town Pedestrian Mall, Winchester VA
Old Town Pedestrian Mall, Winchester VA

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

Virginia State Arboretum, Boyce VA
Virginia State Arboretum, Boyce 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.

Barns of Rose Hill Arts Center, Berryville VA
Barns of Rose Hill Arts Center, Berryville VA

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.

Berryville VA Shops
Berryville VA Shops

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

Peter Miller, framemaker and gilder, Berryville VA

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.

Dinosaur Land VA
Dinosaur Land VA

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

Snow White Grill, Home of the Sliders, Winchester VA
Snow White Grill, Home of the Sliders, 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.

Chop Stick Cafe, Winchester VA
Chop Stick Cafe, Winchester VA

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.

Violino Restaurant, WInchester VA
Violino Restaurant, WInchester VA

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.

Village Square Restaurant, Winchester VA
Village Square Restaurant, Winchester VA

EAT/DRINK: Village Square

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

Where to Stay in Winchester VA

George Washington Hotel, 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.

Bar at George Washington Hotel, Winchester VA
Bar at George Washington Hotel, Winchester VA

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.

Tea at Rosemont Manor, Berryville VA
Tea at Rosemont Manor, Berryville VA

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.

Winchester VA getaway pin


  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

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13 thoughts on “15 Romantic Things to Do in Winchester VA: Finding Patsy Cline”

  1. Just wanted to add 3 more “Best of Winchester” that were overlooked…
    1. The Handley Library is an architectural wonder…ask for a tour!
    2. Bonnie Blue Southern Bakery is a short walk from Old Town and has a great breakfast (after 10 on Sunday) as well as tasty pulled pork and shrimp and grits.
    3. Got kids? Discovery Museum is a great stop. And Jim Barnett Park has 2 great playgrounds as well as a Frisbee Golf course that’s easy to follow. The Toy Store downtown has frisbees and tons more for the kids… have fun!

    Need more?
    Check out Handley High School and the view from the field just west of the buildings.
    Alamo Drafthouse and Cinema has special screenings as well as current films.
    Bright Box Theater is right downtown and hosts live music and comedy 4-5 nights per week.
    Millwood is a short drive away and is fascinating. Great market right across the street with prepared foods/wine etc.

  2. In the summer don’t forget to take in a show at Shenandoah Summer Music Theater at Shenandoah University in Winchester!

  3. Don’t also forget the Burwell-Morgan Mill in Millwood! The historic 18th century working grist Mill is on the National Register, open to the public on weekends, grinds and sells grain, and provides tours to the public. A number of programs are hosted there throughout the year, including Heritage Day on November 4th, which is free, family friendly event!

  4. Nana’s In Middletown offers incredible Irish cuisine and tradional Irish music in the downstairs pub! Definitely worth a visit (or several)!

  5. Sadly One Block West closed! A must visit locale is Cheryl Ash’s Mecca for Cajun-Creole cuisine, Sweet NOLA’s! From the delectable cuisine to the artsy decor, and let’s not forget the live entertainment provided, this truly is a N’Awlins experience!

  6. Thanks for letting me know, Steve. I updated today to reflect that. And thanks for reading and commenting! Malerie

  7. Such fabulous photos makes me want to add Winchester to my itinerary as I plan my US trip next fall. I was going through your post and my wifey just peeked at it and instantly fell in love with the place. Now she is insisting we ADD it for our trip. We are all excited and glad that we saw this. Bookmarked and shared with the rest of the family. Thanks, dear.

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