United States Virginia Virginia Guide Things To Do Essentials Getaways All Virginia Winchester Photos Written by Rachel Cooper Facebook Twitter Linkedin Rachel Cooper is a travel writer who has lived in the Washington, D.C., area for more than 25 years. She is also the author of several books covering the capital and mid-Atlantic regions. Tripsavvy's Editorial Guidelines Rachel Cooper Updated 06/10/19 Share Pin Email Trip Savvy / Rachel Cooper Winchester, Virginia is the oldest city in Virginia west of the Blue Ridge Mountains. The historic district, known as Old Town Winchester, is a four block pedestrian only area with beautifully restored Federalist style architecture, unique restaurants, shops and historic landmarks. See the following photos and get a glimpse of the area. For visiting tips and more information, see Winchester, Virginia - A Visitors Guide 01 of 11 Abram's Delight Museum Photo © Rachel Cooper, licensed to About.com, Inc. Abram's Delight, Winchester's oldest house dating back to 1754, was the home of five generations of the prominent Hollingsworth family. As an early settler, Abraham Hollingsworth built one of the first grist mills in the Valley and his home served as the area's first Quaker meeting house. Today, the property serves as a museum and is furnished with 18th-century art and antiques that tell the story of the early Shenandoah Valley settlers. Address: 1340 S. Pleasant Valley Road (540) 662-6519. (Located adjacent to the Winchester Visitor Center and Shenandoah University, 1.5 miles southeast of Old Town) Continue to 2 of 11 below. 02 of 11 Abram's Delight Cabin Photo © Rachel Cooper, licensed to About.com, Inc. A log cabin located on the west lawn of Abram's Delight Museum dates to 1780 and was reconstructed on the premises in 1967. The cabin is not the original structure located on the property but is similar in style. It is included in the tour of the main house. Continue to 3 of 11 below. 03 of 11 George Washington Statue - Winchester, Virginia Photo © Rachel Cooper, licensed to About.com, Inc. This statue of George Washington is located outside of the George Washington's Office Museum in Old Town Winchester, Virginia. George Washington used a small log building in Winchester as a military office while supervising the construction of Fort Loudoun at the north end of town. The building is now used as a museum showcasing the role that Winchester had on our first president's early military and political career.Address: 32 West Cork and Braddock, Winchester, VA Continue to 4 of 11 below. 04 of 11 Shenandoah Discovery Museum Courtesy of Shenandoah Valley Discovery Museum Shenandoah Discovery Museum is a children’s activity center providing a variety of interactive, hands-on exhibits and programs that focus on the sciences and mathematics, the humanities, and the arts. The museum is located on Loudoun Street in the heart of Old Town Winchester.Address: 54 S Loudoun St, Winchester, VAWebsite: discoverymuseum.net Continue to 5 of 11 below. 05 of 11 Fort Loudoun - Winchester, VA Photo © Rachel Cooper, licensed to About.com, Inc. Fort Loudoun served as the command center for the VA Regiment during the French and Indian War. The fort, named for John Campbell, Earl of Loudoun, was a square fortification designed by George Washington, commander of the Virginia regiment. This marker, situated between the sidewalk and fenced yard describes the fort and its historical significance. Continue to 6 of 11 below. 06 of 11 Winchester City Hall Photo © Rachel Cooper, licensed to About.com, Inc. The Winchester City Hall building was built in 1900 with half of the funding contributed by native Charles Broadway Rouss. Continue to 7 of 11 below. 07 of 11 Old Court House - Winchester, VA Photo © Rachel Cooper, licensed to About.com, Inc. The Old Court House in Old Town Winchester was used as a hospital and a prison during the Civil War. Today, the historic site maintains a nationally recognized collection of Civil War artifacts and provides tours of the building.Address: 20 N. Loudoun Street, Winchester, VAWebsite: www.civilwarmuseum.org Continue to 8 of 11 below. 08 of 11 Handley Library - Winchester, VA Photo © Rachel Cooper, licensed to About.com, Inc. Handley Library is one of the most beautiful buildings in Old Town Winchester. The Beaux-Arts style building opened in 1913 due to funds donated by Judge John Handley of Scranton, Pennsylvania to build a public library.Address: 100 W. Piccadilly St. Winchester, VAWebsite: www.handleyregional.org Continue to 9 of 11 below. 09 of 11 Union Jacks - Winchester, VA Photo © Rachel Cooper, licensed to About.com, Inc. Union Jack Pub & Restaurant is located in the heart of Old Town Winchester in the historic Union Bank Building that dates back to 1878. The restaurant offers authentic British cuisine in a traditional pub atmosphere. This is one of many fine restaurants on the Loudown Street Walking Mall.Address: 101 N Loudoun St. Winchester, VAWebsite: theunionjackpub.com Continue to 10 of 11 below. 10 of 11 Shenandoah Valley Museum Photo © Rachel Cooper, licensed to About.com, Inc. The Museum of the Shenandoah Valley, located just outside of Old Town Winchester, showcases the art, history, and culture of the Shenandoah Valley. The museum complex also includes Glen Burnie Historic House and Gardens, the home of Col. James Wood, who settled on this land in the early 1700s and then donated portions of his property to establish the city of Winchester in 1744.Address: 901 Amherst Street. Winchester, VAWebsite: www.shenandoahmuseum.org Continue to 11 of 11 below. 11 of 11 Glen Burnie Estate - Shenandoah Valley Museum Photo © Rachel Cooper, licensed to About.com, Inc. Located on the grounds of the Shenandoah Valley Museum, the Glen Burnie Historic House and Gardens, offers self-guided tours of the six-acre gardens that surround the main house.Address: 901 Amherst Street. Winchester, VAWebsite: www.shenandoahmuseum.org Was this page helpful? Thanks for letting us know! Share Pin Email Tell us why! Submit What to See and Do in Winchester Virginia Virginia's Best Wine Trails and Tours Best Places to Visit Near Washington, D.C. Top 10 Things to Do in Fredericksburg, VA 20 Great Small Towns Near Washington, D.C. 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