If you’re hoping to indulge in some much-needed retail therapy during your Shenandoah Valley getaway, you’re in luck! From antique shops and boutiques to lovely orchards offering fresh produce, your options for shopping in and around Winchester, VA are nearly limitless. Just to get you started, here are some of our favorite stops for a unique shopping excursion.

Antiques and Reproductions

Blue Peacock Antiques

Winchester, VA  | (540) 323-7641

Over 45 dealers in a 10,000 square foot 1940’s automobile dealership building – a little bit of everything at affordable prices. Open 7 days a week.

The Red Schoolhouse Antiques

Millwood, VA  | (540) 837-3033

For over 25 years, the Red Schoolhouse Antiques has sourced fascinating antique items from all over Europe. Within the shop and adjacent barn, you’ll find small gifts to grand pieces that you’ll want to add to your collection immediately.

The Miller House

Next door to Valley Furniture Stephens City, VA   | (540) 869-2148

High-quality reproduction furniture and accessories (no antiques).  Open Wednesday through Sunday.


Local apples, peaches, asparagus, strawberries, and related products.

Check with us to see what is in season and ask for our back roads map to take you to all our favorite orchards.

Marker-Miller Orchards

Winchester, VA  | (540) 662-1980

Open June through November. Open on Sundays as well in September and October.

Rinker Orchards

Stephens City, VA | (540) 869-1499

Asparagus in the spring, pick your own apples, apple cider, and apple butter in the fall.

Richard’s Fruit Market

Stephens City, VA | (540) 869-1455

Located on the Richard’s fifth-generation family farm, it’s the closest market to the inn. Open July to mid-November.

Woodbine Farm Market

Lebanon Church, VA | (540) 465-2729

Another fifth-generation family farm, the market is on the back way to West Virginia from the inn. A nice selection of local fruit including heritage varieties of tomatoes and apples. Open April through November.

Shopping and Strolling

Old Town Winchester

The four-block-long Loudoun Street pedestrian mall contains restaurants, shops, galleries, and, of course, the old courthouse.  It’s listing in the National Register of Historic Places Travel Itinerary means that it has been recognized for successfully combining history, century-old buildings, and museums to create a charming and sophisticated downtown atmosphere.  

Don’t miss two of our favorite shops in Old Town Winchester that are not on the Loudoun Street pedestrian mall:


Winchester | (800) 967-8676

Gifts, European linens, china, invitations, and a separate building devoted to children’s gifts and clothing.

Simply Charming Boutique

Winchester | (540) 722-2669

Jewelry, gifts, and accessories that you’ll find to be “simply charming”.

Creekside Town Center


Upscale shops and dining just 15 minutes away.

Old Town Winchester

Fine Arts

Eugene B. Smith Gallery

Old Town Winchester, VA   | (540) 667-6190

Watercolors of nearby mountains and historic villages also make great mementos of a visit to the Shenandoah Valley.  Open daily.

Once Upon a Find

Old Town Winchester, VA | (540) 662-1254

Chumley prints and original works by Kathy Chumley Noffke are available at this shop on the Loudoun Street Pedestrian Mall.

Art at the Mill

Burwell-Morgan Mill – Millwood, VA   | (540) 837-1799

Thousands of artists and buyers attend this premier art show each year. It’s an impressive array of art in a beautiful setting.

ApplePeeler by Kathy Chumley “Apple Peeler” by Kathy Chumley


Royal Oak Bookshop  

Front Royal, VA   | (540) 635-7070

Two buildings, side by side, with thousands of used, out of print, rare, sale, and new books.  If you are headed into the Shenandoah National Park in the off-season when the Visitor’s Center is not open, this is a great place to pick up hiking maps and guidebooks (right on the way). Open seven days a week.

Winchester Book Gallery

Winchester, VA  | (540) 667-3444

An independent and locally owned bookshop on Winchester’s Old Town Pedestrian Mall. Open daily.

Blue Plate Books

Winchester, VA  | (540) 662-6657

Feed your need to read with over 10,000 used, first edition, signed, collectible, and antiquarian books. Open every day from 10 a.m. to 8:00 p.m.

Wine and Beer Shops

D’Vine Wines

Creekside Station, Winchester  | (540) 662-9463

Offers over 1,000 different wines and 40 beers. Wine and beer tastings every Thursday and Friday evenings. Open Monday through Saturday (closed Sunday).

Murphy Beverage Company

Old Town Winchester Pedestrian Mall  | (540) 723-9719

“All the wine, the lowest prices and none of the attitude.” Sommelier on staff, large selection of home brewing supplies and Virginia wines. Open daily.

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