Once a small club housed in a trailer, this Portlands landmark now has 550-plus members, a proper clubhouse, more storage trailers and even electricity. It sponsors a popular Learn to Windsurf program that graduates nearly 200 new sailors a year (and gets them on the water in their very first lesson) and a series of in-house clinics for more experienced types that touches on everything from rigging and equipment to high- and low-wind sailing strategies. There are Learn to Race clinics throughout the season, races on Wednesdays, an annual 17-kilometre race around Toronto Island (the Mammoth Marathon) and an annual trip to the surfer’s paradise of Hatteras Island, North Carolina. Beginner lessons usually run from June to September.