Specialty Shops & Boutiques

HandWorks Gallery

Fine American Handcrafts and Global Art. Jewelry, Pottery, Garden Art, Scarves and Handbags, Incense and Soaps, Instruments and Toys, Myriad Adornment...

Incredible Flying Objects

Incredible Flying Objects (IFO) carries a wide variety of fun flying (as well as many non-flying) objects. From darts to juggling equipment, to disc g...

Iron Rose Fitness & Fashion

I am a Certified Personal Trainer, with ISSA for 10 years + and I love Fashion! I enjoy helping people feel good and I enjoy buying and selling unique...

John B. Hayes Tobacconist

We have been helping customers since 1981. Finding that special pipe, pipe tobacco, as well as the perfect cigar for the discerning smoker. Let us ext...

Kimberly’s

Since 1989, we have been developing and refining our retail store in beautiful Old Town Winchester. Kimberly’s features Ladies’ Clothing, ...

Mountain Trails

Outdoor retail (backpacking, camping, hiking, climbing & travel). We have moved! Come visit us at our new location, 115 N. Loudoun Street.

Once Upon A Find Gift Shop

Once Upon A Find offers one of a kind gifts. Quality pewter products including our customized Apple Blossom keepsakes, licensed military & collegi...

Plume House Vape Co.

Plume House, founded by Kirk Gibson in 2015, is a premium vapor boutique in the heart of Old Town Winchester, Virginia. The Plume House team is friend...

Posh Pets Boutique

Posh Pets Boutique is Winchester’s premier destination for pets and those who love them! Featuring: Locally baked treats Plush, eco-friendly bed...

Simply Charming

Simply Charming Boutique carries a vast array of jewelry, home décor, gifts and women’s clothing.

Thinker Toys

Thinker Toys is Winchester’s specialty toy store. Come in to find educational toys, games, puzzles, outdoor toys, puppets, science kits, and muc...

Valley Flag Company

The Valley Flag Company has been serving the Shenandoah Valley for all its flag needs since 1954.  If you need a flag, we’ve got it, from the U....