The Olde Angel Inn on Regent Street is the oldest continuously licensed establishment in Ontario, operating since 1815 on the site of a tavern that was burned during the War of 1812. The interior is properly old — exposed beams, low ceilings, worn floors — and the atmosphere is genuinely comfortable rather than themed. It serves a good selection of Ontario craft beer and local wine alongside pub food.
The inn is a five-minute walk from the Shaw Festival Theatre and fills up quickly on performance evenings. Worth booking a table for post-show dinner in summer. The cellar bar is particularly atmospheric in colder months.