Winchester  is a town in the Shenandoah Valley of Virginia, USA. The town is both a good base for exploring the rest of the valley as well as a picturesque historical site in its own right.
Winchester is located just off of Interstate 81 which runs north into Interstate 70 in Maryland and south into Tennessee. The closest major airport is Washington-Dulles (IAD) which is located about an hour away.
The historical downtown can be seen on foot, but a car will allow you to explore the nearby Shenandoah National Park and scenic Skyline Drive .
- Green Circle - The Green Circle is being developed to allow easy access between the Visitor Center and historic sites by bicycle or on foot.
- The trolley provides easy access around town.
- Several Limousine Companies are available for winery tours.
Loudoun Street Pedestrian Mall
- Patsy Cline Historic House - 608 S Kent Street, Winchester, VA 22601  Patsy Cline was born in Winchester and lived there longer than anywhere else in her life. Her historic home on Kent Street is now a museum with guided tours. Open April-October, $8 adults, $6 children, active military and children under 10 are free.
- Marker-Miller Orchards - Route 622.  Open July-December
- Museum of the Shenandoah Valley, 901 Amherst St., ☎ 888-556-5799, . 10am-4pm. The Museum of the Shenandoah Valley interprets the art, history, and culture of the great valley for which it is named. This regional museum complex includes a historic house dating to the 18th century, seven acres of spectacular gardens, and a museum designed by internationally recognized architect Michael Graves. The museum is open year-round, and the house and gardens are open April through October. edit
- Richard's Fruit Market - 6410 Middle Rd, Middletown, VA 22645  Open June-November, featuring pick your own flowers, local fruits and meats, honey, crafts, and weekend events.
- Shenandoah Valley Discovery Museum, 19 West Cork St., ☎ 540-722-2020, . Open M-F 9-5; Sunday 1-5. A children's museum offering hands-on exhibits and programs that focus on the sciences and mathematics, the humanities, and the arts. $5. edit
- George Washington's Office 
- Stonewall Jackson's Headquarters 
- Abram's Delight 1700s Home 
- Alamo Drafthouse, 181 Kernstown Commons Blvd, ☎ 540-313-4060, . A movie theater with full restaurant service. edit
- Family Drive In Theatre, 5890 Valley Pike, Stephens City, VA (Located on US 11 just off I-81 (exit 307)), ☎ 540-514-6145, . Located just outside of Winchester in Stephen's City, this is one of the few drive in movie theaters left in the state of Virginia. edit
Stonewall Jackson's Headquarters Museum
- Apple Blossom Festival  - Late April/Early May.
- Ghost Tour  - Thrilling, chilling, one-and-one-half-hour easy-walking guided tour exploring the ghost haunts of historic downtown Winchester.
- Civil War Walking Tour  - Educational one and one half hour easy-walking guided tour exploring the events of the Civil War that were centered in historic downtown Winchester.
- Civil War Driving Tour  - Educational four-hour escorted driving tour exploring the events of the Civil War that were centered in the Winchester area.
- Follow the Apple Trail  - Stop at the Visitor Center by Abrams Delight and pick up a cassette or CD and take a leisurely drive through Winchester and Frederick County.
- Handley Library (Handley Regional Library), 100 W. Piccadilly Street (Corner of Rt. 7 and Rt. 11), ☎ (540) 662-9041, . 10-8 (M-W) and 10-5 (Th-S). A library architecturally designed in the Beaux Arts style that opened to the public in 1913. Includes the Nancy Larrick Children's Room, the Middle Kingdom for teens, Information services and the Stewart Bell, Jr. Archives. edit
- Apple Blossom Mall, 1850 Apple Blossom Dr,, ☎ (540) 665-0202, . A mall that is anchored by JCPenny, Sears, and Belk and features 80 stores in addition to a Carmike movie theater. edit
- Winchester Book Gallery, 185 North Loudoun St, ☎ (540) 667-3444, . An independent and locally owned bookstore located right on the Loudoun Street Pedestrian mall. They also have regular book signings, game night every second Friday, and live music. edit
- Old Town Stained Glass Studio, 161 North Loudoun St, ☎ (540) 667-9560, . Located on the north end of the pedestrian mall in the heart of Old Town Winchester, Old Town Stained Glass features custom designed stained glass, fused glass, slumped glass, and mosaic art glass. edit
- Exotic Himalayan Handicrafts, 9 North Loudoun St, ☎ (540) 532-1584. Exotic Himalayan Handicrafts is a shop offering quality handicrafts, decorative items, and clothing from Nepal. edit
- Campbell’s Classic Collectibles, 115 South Loudoun St, ☎ (540) 773-5710. This store offers a wide variety of Collectibles to include Toys, Comics, Movies, Music, Hotwheels, Sci-Fi, Horror, Aliens, Superheroes, Monsters & More! edit
- Pebble in a Pond, 16 South Braddock St, ☎ (540) 327-9765. Winchester’s premier “rock shop” with crystals and gemstones for every pocket and pocketbook and they also sell jewelry, clothing, gifts, home decor, and sacred items such as incense, sage, and essential oils. edit
- The Stock Exchange, 120 East Piccadilly St, ☎ (540) 662-6037, . Consignment shop located right in the center of Old Town Winchester. edit
- Runner's Retreat, 135 N. Loudoun St, . Runners’ Retreat is a running specialty store specializing in athletic shoes and apparel. edit
- Mountain Trails, 115 North Loudoun St., . Outdoor retail store specializing in backpacking, camping, hiking, and climbing gear. edit
- Flavor Pourfection, 27 N. Loudoun St., ☎ 540-662-7687, . Store that features premium extra virgin olive oils, fused and infused olive oils, and aged balsamics and specialty vinegars on tap. edit
- Incredible Flying Objects, 111 North Loudoun St, ☎ 540-678-9993, . Incredible Flying Objects is a toy store that carries a wide variety of flying (as well as many non-flying) objects from darts to juggling equipment, to disc golf, kites and remote control vehicles. edit
- Snow White Grill, 159 N. Loudoun St (Along the central pedestrian walkway), ☎ (540) 662-5955. A cheap and greasy local favorite that serves delicious mini-burgers, birch beer, and milkshakes. Eat inside or out. edit
- Cork Street Tavern, 8 West Cork Street (In old town Winchester), ☎ (540) 667-3777. American food including ribs. Outdoor seating during summer. edit
- Peru’s Chicken Restaurant, 3050 Valley Ave Ste 101, ☎ (540) 545-7060, . Peruvian take out restaurant specializing in rotisserie chicken. edit
- Delicias Mexicanas Cafe, 1709 Berryville Pike Ste B, ☎ (540) 535-2082. Located inside of an Exxon gas station this Mexican restaurant is known for their tacos con carnitas and tamales verde. edit
- Thai Winchester, 24 S Loudoun St, ☎ (540) 678-0055. An authentic Thai restaurant located right in Winchester's Old Town. Be sure to try their drunken noodles. edit
- Violino Ristorante Italiano, 181 N Loudoun St, ☎ (540) 667-8006, . Family owned restaurant specializing in Italian cuisine. edit
- Bonnie Blue, 334 W Boscawen St, ☎ (540) 686-7490, . Restaurant known for putting a unique twist on staples such as biscuits and gravy, shrimp and grits, and pulled pork sandwiches. edit
- Sweet Nola’s, 688 N Loudoun St, ☎ (540) 667-6652, . Restaurant specializing in Southern/Cajun cuisine. Be sure to try their alligator sausage and gumbo. edit
- Lloyd’s Tropical Island Coffee and Café, 39 West Piccadilly St, ☎ (540) 905-8022. Jamaican restaurant known for serving their Blue Mountain coffee, Jerk Chicken and Red Snapper Fish. They also have a gift shop selling also carry island crafts and souvenirs. edit
- Chopped Corner Store, 202 E Piccadilly St., ☎ (540) 323-7994. Chopped Corner Store is a convenience store and has a takeout menu offering breakfast, lunch, and baked goods. edit
- La Nicoise Café, 12 South Braddock St, ☎ (540) 722-4557, . A café specializing in French cuisine owned by proprietor Frederic Boukaïa, who makes frequent appearances to greet new patrons as well as now familiar faces. edit
- Roma Old Town Wood-Fired Pizzeria, 21 N Loudoun Street, ☎ (540) 667-2743, . Restaurant specializing in Greek/Mediterranean and Italian food with pizza, sandwiches, craft beer, and more. edit
- Tater Hill Tavern, 618 South Loudoun Street (inside the Nancy Shepherd House Inn), ☎ 540-247-5073, . by appointment only. This amazing ancient tavern ale and wine room is inside the Nancy Shepherd House Inn. If you like historic early taverns, this one is a must see while visiting Winchester, but you must be an overnight guest of the Inn for the privilege...or if you are not an overnight guest, you might try your luck and call to see if the innkeepers will invite you in anyway. It's worth a try. edit
- The Union Jack Pub & Restaurant, 101 North Loudoun St, ☎ (540) 722-2055, . British Pub located in Old Town Winchester that has a large selection of beers on tap. edit
- Espresso Bar & Café, 165 North Loudoun St, ☎ (540) 686-7209. Coffee shop known for their French Pressed coffee, sandwiches, and nice atmosphere. edit
- Winchester Brew Works, 320 N. Cameron St, ☎ (540) 692-9242, . Nanobrewery located one block north of the Old Town Loudoun Street Mall, serving modern flavorful brews. edit
- Alesatian Brewing Co., 23 N. Loudoun Street, . Alesatian Brewing Co. is a local nanobrewery located above Roma’s Old Town Wood-Fired Pizza that specializing in bringing fresh, unique, and classic brews. edit
- Old Waterstreet Inn - 19th century house. Some rooms with fireplace; breakfast and cocktails included. $120-155.
- George Washington Hotel - Luxury suites with fireplaces and whirlpool tubs. Spa and pool.
- Long Hill Bed & Breakfast  - #1 inn in the South. Custom 10,000 sq.ft. house on 20 A. Savor an award winning family style gourmet breakfast. View birds & wildlife. Great getaway; vacation anchor. Shoot pool; work puzzles; Good food, good rest; feel like family when you leave.
- Nancy Shepherd House Inn Bed and Breakfast, 618 South Loudoun Street Winchester VA 22601 (right downtown on Winchester's main street), ☎ 540-247-5073, . Great value with a fantasic breakfast. Very interesting historic inn right downtown with excellent restaurants, shops, pubs, coffee houses, and museums all around. Four extremely comfortable & cozy bedrooms, two with fireplaces. $79 - $139. edit
- The Shenandoah National Park is about 50 miles south on I-81.
- Skyline Drive runs parallel to I-81 south into Tennessee.
- Washington, D.C.
- Harper's Ferry, Antietam, and Gettysburg are within an easy drive for visiting Civil War Battlefields and learning about the Civil War.
- Berkeley Springs which is a quaint small town famous for it's springs and large artist community is located about 45 minutes away from Winchester on US 522.
- Shepherdstown is a quaint small town with upscale dining and bed and breakfast inns located only 45 minutes away.
|Routes through Winchester