Canandaigua

At the north end of Canandaigua Lake, Canandaigua pairs a lively Main Street with one of the region's best-loved outdoor stages. The CMAC amphitheater draws major touring acts all summer, while breweries, wineries, and downtown bars keep the calendar full the rest of the year. It's an easy half-hour from Rochester, so big-name shows and a relaxed lakeside night out are both on the table. Late spring through early fall is the sweet spot, when the lakefront and the pier come alive most weekends.