At the annual Blues & Brews Festival, September sunlight saturates mountains cloaked in green and gold trees—setting a colorful stage for three days of funk, rock, soul, and blues. “This event is overshadowed by all the other Telluride festivals,” says General Manager Alex Rollinson. “But it’s my favorite—and one of the few family-friendly options where kids 11 and under are free.

The roar of the Upper Piedra River is loudest when the cold, hard snow begins to melt in Telluride. So in late May, adrenaline junkies head straight for the river’s frigid Class IV rapids. “Spring runoff turns the Piedra into a raging river, perfect for intense white-water rafting,"...

Locals lovingly call them 14ers—the majestic, rugged mountains rising above 14,000 feet that are heavily concentrated in Colorado, which has the most of any state. The quest to dominate these treacherous summits has captivated many adventurers. “The Telluride area has 14 of the state’s 53 peaks,” Troy Trinh says. “My favorite, Wilson Peak, happens to be one of the toughest. You might recognize its northern face from the Coors Light can.”