First Friday Old Town Winchester:On the First Friday of every month, Old Town Winchester plays host to artists with special gallery events, muscians playing in restaurants and cafes, and many of our shops stay open late. It is a great time to stroll our historic streets and a great place to meet new and favorite friends. Every month is something a little different. Learn more here

Shenandoah Apple Blossom Festival®: A series of more than forty events includes: band competitions, dances, parades, carnival, dinners, luncheons, wine festival, a 10K Race, the Coronation of Queen Shenandoah, two large parades, and celebrities. The Festival is an event the whole family can enjoy. Learn more here

Old Town Splash Pad:Come cool off at the Old Town Winchester Splash Pad located on the south end of the Loudoun Street Mall.

Wilson Wild animal park: The Park is home to more than 40 species and has been privately owned and operated since 1976. The park is set on 25-acre plot and has a gravel pathway approximately a mile long!

Dinosaur Land: Step into the world of the prehistoric past, where visitors can turn back the pages of time to the Mesozoic era, when dinosaurs were the only creatures that roamed the earth. Dinosaur Land has been attracting visitors since around 1963.

Appleland Sports Center: A great place for golfing, mini golfing, and go carting, or take a swing at the batting cages.

Winchester parks: Your guide to all the local Winchester parks.

Rock Harbor Golf Course: Rock Harbor Golf Course is located in the heart of the famed and historic Shenandoah Valley, home of Patsy Cline. Now, the home of Rock Harbor Golf Course. Thirty-six (36) uniquely designed golf holes

Family Drive-in theater:We are a two screen drive-in theatre, offering first run movie features at “Family Affordable Prices”. We have a double feature policy (offering movie patrons two-first run films per night; per screen) for one low admission price! The Family Drive-In was built by The Dalke family and opened on June 14, 1956. The theatre is currently in it’s 60th year of operation!  We are the only remaining drive-in theatre in the Washington metropolitian area.

Shenandoah Valley Discovery Museum:Our mission at the Shenandoah Valley Discovery Museum is to spark curiosity and inspire learning through creative play.

Museum of the Shenandoah Valley: Museum of the Shenandoah Valley (MSV) is dedicated to preserving and enriching the cultural life and heritage of the Valley.

Washington’s Office Museum: George Washington used a little log building, now the middle room of George Washington Office Museum, as a military office from September 1755 to December of 1756 while Fort Loudoun was being constructed at the north end of town.

Winchester-Frederick County Historical Society: The Society maintains five museums all located in Winchester, Virginia – Abram’s Delight, George Washington’s Office, and Stonewall Jackson’s Headquarters, an 18th Century Valley Cabin and the Hollingsworth Mill.

Handley Regional Library: Judge John Handley of Scranton, Pennsylvania left $250,000 in his will to “ . . . open a Public Library for the free use of the people of the city of Winchester forever.” And in 1913, this gorgeous library opened to the public.

Bright Box Theater:a dynamic performance and event venue, located at the heart of Winchester, VA, on the newly renovated Loudoun Pedestrian Mall. Besides showcasing some of the best music and performances in the area, we are also a superb venue for comedy shows, weddings, private parties, reunions, and fundraising events.

Movie Theaters:

Alamo Draft House: Cold beer, hot movies, and delicious snacks and meals; The Alamo Drafthouse is dinner, drinks, movies and events, all under one roof.

AMC Apple Blossom 12: Experience the difference of AMC amenities. From spacious rocking seats to luxury recliners, innovative menus and premium offerings like IMAX, Dolby Cinema, and Prime at AMC, AMC Theatres offers a range of ways to get more out of movies.

Old Town Winchester Shopping:

A few of our favorite stops are Simply Charming Boutique , & Kimberly’s