Start off in Durango, where you can raft the Animas or hike the start of the Colorado trail. Hit Bread bakery for cookies and danishes before you head out of town.
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You can take the train from Durango to Silverton, but you can also drive over Molas Pass. In Silverton, mountain bike at the ski resort, or hike in the San Juans. Lodging and dining options are slim, but you should probably drink beers at Miners Tavern.
The stretch of highway 550 from Red Mountain Pass to Ouray is called the Million Dollar Highway, because of the millions of dollars in gold and silver miners expected to find. It’s also got million dollar views (zing.) Ouray is known for ice climbing, but in summer there’s good local rock climbing too.
Head out of Ouray towards Ridgway and descend out of the mountains for a while. Stop for a soak at the Orvis Hot Springs. The thrift store on the corner where you turn towards Telluride can be a gold mine for vintage bikes.
Drive up the canyon to Telluride. On summer weekends, it’s not hard to time it right so you hit a festival, like Blues and Brews, or the Telluride Film Festival. In the morning head to the Steaming Bean for people watching and the best blueberry muffins in the world. At night, get Thai food at Siam, drinks at There, and your swerve on at the Llama.