Culture, Architecture, and Shenandoah Valley History
Friday, April 24
Arrive and check into your accommodations. Stay in the heart of the historic district at one of Old Town Winchester’s charming bed and breakfasts – Fuller House Inn (c. 1830), Nancy Shepherd House (c. 1772), or Old Waterstreet Inn (c. 1840).
Spend the evening at the Bloomin’ Wine Fest, which runs until 10pm in Old Town Winchester. Enjoy tasting wines from 20 Virginia wineries and craft breweries too. The evening will be full of live musical entertainment, delicious festival food, and displays by local artisans.
Saturday, April 25
Take some time to explore the historic district on your own. A self-guided walking tour brochure detailing the history and architecture of Old Town is available from the Winchester-Frederick County Visitors Center or Old Town Welcome Center. Several museums are within walking distance, including George Washington’s Office Museum, Stonewall Jackson’s Headquarters Museum, and the Shenandoah Valley Civil War Museum.
Many of the buildings in Old Town Winchester have unique histories and you can enjoy lunch at one of them – Union Jack Restaurant and Pub in the restored c. 1878 Union Bank building, Village Square and V2 Oyster Bar in the former Miller’s Drug Store (founded 1764), and the Cork Street Tavern, an 1830s building that took fire during the Civil War and is rumored to be haunted.
If you purchased a two-day pass, return to the Wine Fest (11am-6pm) for more! Or, purchase tickets for Virginia’s Historic Garden Week Tours, which are available at the Winchester-Frederick County Visitors Center. Spend the afternoon touring four incredible private homes and gardens, with exclusive, one-day access for this special event. The tour also includes a stop at the must-see Museum of the Shenandoah Valley for tea.
Sunday, April 26
For a relaxing end to your trip that includes mountain views, spring gardens, and Shenandoah Valley history, visit Belle Grove Plantation in nearby Middletown. The 1797 Manor House was built by Major Isaac Hite and his wife Nelly Madison Hite, sister of President James Madison. Breathing in the clean country air will leave you feeling refreshed.
Before departing for home, consider ending your visit with a local tradition at Apple Blossom time – a leisurely country drive among the apple orchards. (Your route could include: Cedar Creek Grade, Marlboro Road, Middle Road, and Barley Lane). View the rows and rows of pink and white blossoms set among the backdrop of the Blue Ridge and Allegheny Mountains in the distance.