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Durango & Silverton Narrow Gauge Railroad . The San Juan Skyway covers 236 miles of terrain across the beautiful Southwest corner of Colorado. Starting in Durango, the skyway travels in a loop passing through Cortez, Dolores, Rico, Telluride, Ridgway, Ouray, and Silverton. Travel over high mountain passes, historian mining towns, and through the heart of 5 million acres of both the San Juan and Uncompahgre National Forests.