Woodstock is a compact, walkable Shenandoah Valley town with a charming historic downtown, local shops and eateries, and a friendly small‑town feel that makes multi‑week stays comfortable and interesting.
Outdoor options are minutes away — from Skyline Drive and Shenandoah National Park to family‑friendly resort activities at Massanutten — so weekends can be full of hiking, mountain biking, and seasonal events rather than boredom.
When you want more city options, Harrisonburg (about a 38‑mile drive) offers a lively college‑town dining/brewery scene and Winchester (≈34 miles) adds larger shopping, medical centers and transit for occasional long-weekend needs.