Winchester, Virginia is a lively, historic small city in the northern Shenandoah Valley with a walkable downtown of restaurants, breweries, wineries and a strong arts and healthcare community, plus easy access to hiking, Skyline Drive and Civil War sites—comfortable and interesting for multi‑week stays.
For bigger‑city variety within a short drive, Frederick, MD and Hagerstown, MD provide more shopping, dining and regional transit options for weekend escapes.