The largest keel boat regatta in all of the land (Canada) takes over the town of Chester for a weekend every summer, bringing sailors from North America and beyond to Nova Scotia waters to battle each other—and the elements—on the water. Cheer ’em on, and take part in the festivities—nightly live music from Hopping Penguins, Party Boots and Asia Nu Gruv, food trucks and other dockside entertainment. —Allison Saunders