Winchester VA And Environs: Patsy Cline, Civil War Chaos, Farm Markets and Great Eats

Old Town Winchester Pedestrian Mall at Sunset

Old Town Winchester Pedestrian Mall at Sunset

WHY GO: 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. Years later, Country Music star, Patsy Cline, drove her neighbors crazy with her teenage wild-girl antics. And according to some folks, Winchester is one of the most haunted towns in Virginia. You’ll discover all of this along with bountiful restaurants, farm markets, a tiny arts village, a recently renovated historic downtown hotel, and enough history in the Winchester area to keep you busy for days.

Things to Do in Winchester VA

Patsy Cline Home, Winchester VA

Patsy Cline Home, Winchester VA

TOUR: Patsy Cline Home. Dirt poor, Winchester-born Virginia Hensley had 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, married Gerald Cline, changed her name to Patsy, divorced Cline and married Charlie Dick (who is still alive as of October 2014) and went on to fame and fortune before dying tragically in a plane crash in 1963 at 31 years old.

A 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.” $8 adults, $4 youth for 45 minute tour. Open April 1-Oct 31 Tues-Sat 10-4, Sun 1-4, Nov-Dec, Fri, Sat 10-4, Sun 1-4. Jan-March by appointment only.

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, in use until 1987, and opened as a Civil War Museum in 2001. 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, and you’ll see 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. $5 adults, $3 kids. May-Oct Mon-Sat 10-5, Sun 1-5: Nov-April Wed-Sat 10-5, Sun 1-5.

Museum of the Shenandoah Valley, Winchester VA

Museum of the Shenandoah Valley, Winchester VA

VISIT: Museum of the Shenandoah Valley. Ken Burns hung out here while the Patsy Cline exhibit was up (2013-2014) to research for his upcoming documentary on Country Music. Located on acres of farmland and incorporating the Wood-Glass manor, this $20 million Michael Graves designed museum is a stunning tribute to Virginia’s Shenandoah Valley. 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 along with videos, films, country home dioramas juxtaposing an 1830’s kitchen with a 1930’s kitchen, and the complete dining room from Glen Burnie – the late 1700’s manor house which you can also visit.

Gardens of Glen Burnie, Museum of the Shenandoah Valley, Winchester VA

In fact, the acres of gardens at Glen Burnie are an attraction here in and of themselves, with water features and Asian flourishes. A healthy reason to get outside and wander. Open Tues-Sun 10-4, $10 adults, kids under 12 free.

Virginia State Arboretum, Boyce VA

VISIT: State Arboretum of Virginia on Blandy Experimental Farm. You gotta love a gorgeously landscaped property with the slogan, “We don’t raise crops or cattle, we raise scientists.” This stunning 720-acre estate, complete with former slave quarters that have been converted into classrooms and labs, integrates 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.

Rooftop Shenandoah County Discovery Museum Winchester VA

VISIT: Shenandoah Valley Discovery Museum. The SVDM’s vision – “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 science experiments and chances to play, this relatively new museum swarms with families on rainy days. Don’t forget the incredible rooftop – with a zany zig-zaggy tiled house. It’s a perfect perch from which to watch the sunset.

Homestead Farm at Fruit Hill Orchard, Winchester VA

FAMILY FARM: Fruit Hill Orchard and The Homestead Farm, Winchester. Everything in this country-home market is organic and non-GMO, and 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

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, where you can pick up organic produce and country knick-knacks and, on Thursday evenings from July to November, listen to live Bluegrass on the front porch, complete with home-cooked meal – all for $10. Meal starts at 6:30, music at 7.

Winchester Cider Works VA

TASTE: Winchester Ciderworks. You’ll find this hard cider brewery next door to The Homestead Farm. My favorites – the purple 522, a black-current cider, and Malice, its best seller.

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 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. This market and fruit farm offers a true hands-on harvest experience; pick your own apples (22 varieties from July to November), peaches, blackberries, raspberries, and other fruits. The market shop offers a bountiful selection of produce, jams, ice cream, fudge, prepared foods, and the very popular cider donuts – best eaten when just out of the oven.

Barns of Rose Hill Arts Center, Berryville VA

ARTS/SHOP: Town of Berryville. 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

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.

Peter Miller, framemaker and gilder, Berryville VA

Hailing from Woodbury/Southbury Connecticut, the internationally renowned Miller moved to Virginia to be near family, and recently opened 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.

Abram's Delight, Winchester VA

Abram’s Delight, Winchester VA

VISIT: Abram’s Delight, George Washington’s Office Museum, Stonewall Jackson’s Headquarters. Stop into the Winchester Visitor’s Center (open daily 9-5) and you’ll be directed next door to the oldest compound in the state, “Abram’s Delight” (where you can purchase tickets to all three properties). 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, expanding the family business into a mill and building a stone home reminiscent of their 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, 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, 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: The restored Hudson River Gothic Revival house that belonged to the great-grandfather of Mary Tyler Moore, Lt. Col. Lewis T. Moore, 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, Mon-Sat 10-4, Sun 12-4, $5 per property, $10 block ticket for all three properties.

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.

Jean Woolsey and J.P Murphy; Ghost Tours of Old Town Winchester VA

Jean Woolsey and J.P. Murphy, Ghost Tours of Old Town Winchester VA

TOUR: Ghost Tours Old Town Winchester Virginia. If you are a fan of ghost tours (like me), you might be surprised when your guide, “sensitive” Jeanette Woolsey, dressed in a black Victorian mourning dress, hands you a Spirit Monitoring Device and enlists you into her ghost-hunting world. Yes, you will also learn about the history of Winchester along the way. Woolsey begins the tour (which runs three times a night and can be customized) at the “very haunted” George Washington Hotel where, employees have noted, ballroom doors open and shut on their own.

Jean Woolsey at Mount Hebron Cemetery leading Ghost Tour of Old Town Winchester VA tour.

Jean Woolsey at Mount Hebron Cemetery leading Ghost Tour of Old Town Winchester VA tour.

At the entrance to Mount Hebron Cemetery – final resting place for thousands of Union and Confederate troops – Woolsey brings out her arsenal of monitoring devices, which click, light up, and even speak. You’ll walk some of the “45 blocks of history,” stopping by George Washington’s military office (September 1755 to December of 1756 while Fort Loudoun was being constructed at the north end of town): all so spooky in the darkness. Runs most nights; check Facebook page for available times Old town candle light ghost tour, $12, Blue and Grey ghosting tour, $18 – Extreme ghost hunting midnight tour $25 – Haunted Pub Crawl tour, $29.

SHOP: Murphy Beverage Co. The coolest of wines and the rarest of ales, Murphy’s is arguably one of the only beer and wine sellers with a sommelier on staff. Located on the Old Town Mall.

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 and 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

Sweet NOLAs Winchester VA

EAT: Sweet NOLA’S. Any restaurant named for “New Orleans LA” has a lot to prove this far northeast. Chef-owner, Cheryl Ash, delivers the Cajun goods. In spades. Everything, from the Creole Potato Salad ($3), to cornmeal-dusted Fried Okra ($3), Gumbo ($8.75), Satchmo’s Red Beans and Rice ($8.50), to Po’ Boys of all varieties is such drool-eliciting-good Louisiana swamp food, at such low prices, it made me forget what American State I was in, let alone what decade. All this in a dazzling, sparkly, drenched in color space, best described as Early Mardi Gras. Laissez les bons temps rouler!

Steamy's, Winchester VA

Steamy’s, Winchester VA

EAT/BREAKFAST: Steamy’s Cafe. Across from the GW Hotel, Steamy’s doesn’t look like much from the outside. But it’s “Friends” cute inside –especially the back room where you’ll find tables, chairs and bookshelves full of books you can purchase for $3. Aside from the crafted coffees, humus with veggies and smoothies, you’ll find from-scratch pretzel-like bagels made before your eyes by John, the pastor of, a non-denominational “homeless and lost outreach center.” Just down the street, Another Chance counsels and feeds and provides showers for anyone who needs it. “We just read The Book and put it into practice.”

Snow White Grill, Home of the Sliders, Winchester VA

Snow White Grill, Home of the Sliders, Winchester VA

EAT/THROWBACK: 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. In a tiny corner-store space, what the café lacks in atmosphere it more than makes up for in quality (and cost) of the food. The most expensive entrees don’t inch much above $10. Pho is $9, Sushi Rainbow Roll is $10, and Marinated Rib Eye Stir Fry is a relative King’s Ransom at $13. 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. This little white tablecloth spot proves that Virginia can do classic Italian exceedingly well. Nibble on Zucchini Flowers, homemade pastas and freshly made gelato.

Village Square Restaurant, Winchester VA

Village Square Restaurant, Winchester VA

EAT/DRINK: Village Square. It’s 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). This venerable old hotel, built in 1924 and renovated in 2008, is just a block away from the car-free outdoor Pedestrian Mall. Gold and offwhite rooms were not stripped of their “pre-war” charm – 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. Rooms and suites from $119-$369.

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, and steeped in history. Come to this spectacular home for Manor House Tea ($44) on select Fridays and Sundays, or book one of the themed rooms, named for Roosevelt, Eisenhower, Kennedy, Johnson, Nixon, Einstein and others who stayed in here. It’s not just for brides and grooms. $250-$350 per night.

In Category: Arts & Culture, Virginia

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,, 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.

Show 14 Comments
  • GARY AUERBACH October 29, 2014, 7:46 am Link

    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.

  • Malerie Yolen-Cohen October 29, 2014, 8:08 am Link

    Thanks for the additional information, Gary! And thanks, also, for reading.

  • Michael A. Zimmerman October 29, 2014, 2:21 pm Link

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

  • Amy jewell January 22, 2017, 9:13 pm Link

    Can you tell me status of taylor inn… story is that because it’s so haunted they can’t keep businesses there. I understand taxes are owed also so maybe no one knows when it will open again. Do the ghost tours of Winchester go thru the inn? Thanks.

  • Vanessa Junkin September 29, 2017, 11:05 am Link

    Enjoyed reading this, Malerie! You covered a lot in a nice article. 🙂 Great to see you again at MATPRA!

  • Steve Moyer September 29, 2017, 1:55 pm Link

    I believe One Block West has closed.

  • Susi Bailey September 29, 2017, 10:00 pm Link

    Thank you for including Berryville, especially the shops & Barns of Rose Hill!

  • Nathan Stalvey September 30, 2017, 5:34 pm Link

    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!

  • Patrick Kelly October 1, 2017, 11:43 am Link

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

  • Patrick Kelly October 1, 2017, 11:46 am Link

    Sadly One Block West closed!

  • Patrick Kelly October 1, 2017, 11:52 am Link

    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!

  • Malerie Yolen-Cohen October 25, 2017, 12:17 pm Link

    Thanks, Patrick – I updated today to reflect that. Thanks for reading! Malerie

  • Malerie Yolen-Cohen October 25, 2017, 12:18 pm Link

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

  • Dustin November 28, 2017, 1:43 pm Link

    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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