Telluride has two distinct peak seasons and several festivals in between, which means there is rarely a bad time — only a question of what you want.
Ski season runs December through April, with January and February typically offering the best conditions. The mountain gets less traffic than comparable Colorado resorts closer to Denver, so even peak weekends feel manageable.
The summer festival season is the other major draw. The Telluride Bluegrass Festival in mid-June is the most celebrated, drawing bluegrass, folk, and Americana acts to a free festival ground in town (paid camping and VIP tickets available; many people watch from the surrounding hillsides for free). The Telluride Film Festival in September is the town's most prestigious event and has a reputation for launching award contenders. The Jazz Festival in August and the Wine Festival in June fill the shoulder weeks.
May and November are the quiet months, when many businesses close or cut hours. They are also when you can walk Colorado Avenue without navigating crowds, find a restaurant table without a reservation, and get a sense of what the town is actually like when it is not performing for visitors.