855/857/859 James Street

Downtown Woodstock has a small-town feel, but step off Dundas Street and you’ll see a city that’s grown into something more layered. There’s the historic charm—brick facades, a post office clock tower, tree-lined streets—but also the hum of daily life from local farmers’ markets, nearby trails, and a busy fairground that turns electric each summer during Cowapolooza, the city’s signature festival.

Daily life here moves at a relaxed, walkable pace. Southside Park draws locals year-round with its winding trails and scenic pond, while the Museum Square lawn hosts regular concerts and community events. Residents often stroll or bike to run errands downtown or grab a coffee before catching a show at the historic Market Centre Theatre. Woodstock’s size makes it easy to navigate, and being just off Highway 401 means trips to London or Kitchener are always within reach.