Happy Wednesday, Winstigators!

There are roadside stops and then there are roadside stops…the type of place you pull into for a quick coffee or bathroom break and somehow leave with a pie, a six-pack, a sandwich, a bottle of wine and make the note to come back and explore it again when you have more time.

Hill High Marketplace is absolutely that kind of a roadside stop.

Out on Route 7 between Winchester and Leesburg is where you’ll find Hill High. It’s a favorite place of mine and I found an excuse to stop in over this past weekend to find a Mother’s Day bottle of wine for my wife and, as usual, I left with more than I bargained for. There’s a great bakery inside, a market with fresh soups and sandwiches and a fantastic beer and wine selection. I’d stopped to find a bottle of wine but also walked out with a carrot cake cupcake and a beer from one of my favorite microbreweries. No regrets.

While the cupcake was great, Hill High’s calling card is Mom’s Apple Pie and it’s the real deal. According to Hill High, Mom’s uses local and organic ingredients where possible, including fruit from their nearby farm and they’re known for preservative-free pies made with fresh Shenandoah Valley apples.

But Hill High is more than dessert. It’s the kind of place where you can grab lunch (the sandwiches are made to order and thick), browse the market, check out the wine and beer selection and realize this is what a locally owned and operated roadside stop really should be. There’s local beer, wine, meats, dairy, produce when in season and enough thoughtfully curated odds and ends to make the place feel like more than just somewhere to pull off the road. And when I didn’t know which bottle of wine to grab for my wife on Saturday, there was someone there to help walk me through the options and make the right selection.

But the best thing about Hill High is that it works whether you planned on stopping or not. Passing through on the way to Loudoun? Stop. Heading home to Winchester from Purcellville, Leesburg, Bluemont or wine country? Stop. Need something better than a chain coffee and a bag of chips? Absolutely stop.

Go for the pie. Stay for lunch. Leave with beer, wine and something baked that you absolutely did not need but looked great and was worth trying.

Clarke County Ruritan Fairgrounds, Berryville - Lucketts Spring Market, May 15 - May 17

Broken Window Brewing Company, Winchester - Songwriter's Night, May 15, 7pm - 10pm

Hollywood Casino, Charles Town - The Wallflowers at Hollywood Casino at Charles Town Races,

The Kurtz Building, Winchester - Guided History Walking Tour of Old Town Winchester, May 15, 6pm

Fort Shenandoah, Winchester - North-South Skirmish Association’s National Competition, May 15 - May 17

Winchester Little Theatre, Winchester - Winchester Little Theatre: Calendar Girls, May 15 - May 30

ShenArts - Shenandoah Arts Council, Winchester - Formed & Fired, May 15, 5pm - 7pm

Warren Heritage Society Inc., Front Royal - Corks and Chords - Bearded Harmony Plays the Warren Heritage Society, May 15, 6pm

Bush Tabernacle Skating Rink, Purcellville - Loudoun County Ducks Unlimited Banquet + Auction, May 15, 6pm

Tally Ho Theater, Leesburg - Girlfriend In A Coma: A Tribute to Morrissey & The Smiths, May 15, 7pm

Harpers Ferry - Harpers Ferry World Fiddle Day / May 15-16 2026, May 15 - May 16

5050 Taphouse, Winchester - Drag bingo at 5050 Tap House, May 15, 10pm

Clear Spring Vol. Fire Co. Special Events Bldg, Clear Spring - National Pike Festival & James Shaull Wagon Train 2026 “Kick-off”, May 15, 3pm - 9pm

Salamander Resort, Middleburg - Salamander Uncorked: Cabernet Sauvignon - Old World vs. New World, May 15, 4:45pm - 6:30pm

Blue Ridge Shadows Golf Club, Front Royal - 2026 John H. Enders Charity Golf Tournament, May 15, 1pm

Museum of the Shenandoah Valley, Winchester - Plant Sale, May 16 - May 17

Fort Loudoun, Winchester - Fort Loudoun Day Living History Event, May 16, 11am - 3pm

Winchester Brew Works, Winchester - Winchester Brew Works 10th Anniversary Party, May 16, 2pm - 6pm

First Baptist Church of Winchester, Winchester - Arts Chorale of Winchester Spring Concert, May 16, 7pm

The Winchester Book Gallery, Winchester - Author Event: Bryan Lienesch - Safe Harbor, May 16, 11am - 1pm

The Winchester Book Gallery, Winchester - Author Event: June Smalls - Hear Them Sing, May 16, 2pm - 4pm

Lincoln Strawberry Festival, Hamilton - Lincoln Strawberry Festival, May 16 - May 17

Cana Vineyards and Winery of Middleburg, Middleburg - Slow Flow Yoga with Rhonda, May 16 - July 18

Middletown Community Park, Middletown - Vintage Baseball Game, May 16, 2pm - 4pm

Connected Communities Inc, Winchester - Taste of Community Food Truck Festival, May 16, 11am - 4pm

Sky Meadows State Park, Delaplane - National Kids to Parks Day: Little Explorer Day of Play, May 16, 11am - 2pm

Four Seasons Books, Shepherdstown - Get in, Loser, We’re Smashing the Patriarchy Book Club: Her One Regret, May 16, 7:30pm

Sam Michaels Park, Harpers Ferry - Serve it Forward Pickleball for Good, May 16, 8am - 9pm

Bad Habits Bar & Grill, Martinsburg - Appalachian Noise Fest 2026, May 14 - May 16

Clear Brook Park, Clear Brook - 2026 WALK FOR LIFE, May 16, 6pm - 8pm

Whites Ferry Brewery, Leesburg - Stand Up Comedy Night at Whites Ferry Brewery, March 20 - May 16

The Morven Park International Equestrian Center, Leesburg - Morven Park Summer Show Series I, May 16 - May 17

Kitchens Orchard & Farm Market, Falling Waters - 2nd Annual Car Show On The Farm, May 16, 8am - 4pm

Hollywood Casino at Charles Town Races, Charles Town - One Night of Queen, May 16, 8pm - 10pm

Tally Ho Theatre, Leesburg - Reverend Peytons Big Damn Band at Tally Ho,

Washington County Agricultural Education Center, Boonsboro - Quad State Pickle Fest 2026 Vendor APPLICATION, May 16 - May 17

Lost Barrel Brewing, Middleburg - Out West Fest, May 16, 11am - 8pm

The Winchester Book Gallery, Winchester - Author Event: Vesper Doom - The Binding of Bloom Mountain, May 17, 12pm - 2pm

Main Street and Shafer Park, Boonsboro - National Pike Festival Wagon Train, May 17, 12:30pm

Breaux Vineyards, Purcellville - Live Music with Melissa Quinn Fox, May 17, 2pm - 5pm

Shenandoah Lodge & Athletic Club, Lake Frederick - Watercolor Workshop - Peonies, May 17, 10am - 12pm

The Back Alley Garden Tour & Tea, Shepherdstown - 2026 Back Alley Garden Tour & Tea, May 16 - May 17

Theatre Shenandoah, Edinburg - James & Joel Featuring Clay Mottley, May 17, 3pm

Hogback Mountain Pony Rides, LLC, Hamilton - Loudoun Farm Tour, May 16 - May 17

Summit Point Motorsports Park, Summit Point - BSRS Event #1 - VRG Jefferson 500, May 14 - May 17

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Have fun out there!