Telluride is so full of life-affirming activities, megawatt natural beauty, and homey communal kindness it'll have you questioning why you're not living there. Pay a visit in the summertime and you can spend your days hiking and biking along the absurdly idyllic alpine landscape (fields of wild flowers, cerulean lakes), fly fishing in trout-filled streams and rivers, and rock climbing the legendary Via Ferrata (possible for all skill levels). And when you find your adrenaline ebbing, you can play the 18-hole Telluride Golf Course dwarfed and surrounded by the Rocky Mountains.
Alternatively, hit up a free concert or festival. The Summer Concert Series runs from June 21 through August 16, and Telluride plays host to more than 30 festivals. Come in the winter and you can hit the slopes for skiing, snowboarding, heli-skiing, back-country skiing—and pursuits like ice climbing, fat biking, and dog sledding. Telluride is known for being remote (it's a small, former mining town that's not as easy to get to as other ski resort hot spots), which means you won't be waiting on lines for lifts or dodging people left and right.
Where to stay: Madeline Hotel and Residences takes the cake. Set in the heart of Mountain Village, the Madeline is Telluride’s only four-diamond hotel (it’s “refined, stylish with upscale physical attributes” and has a “high degree of hospitality,” per AAA). Aside from being impeccably designed and staffed, the Madeline gives you prime ski-in/ski-out service in the winter, has a spectacular Sky Terrace complete with outdoor pool, multiple hot tubs, and killer skyline views, and is close to the town's free gondola so you can easily access downtown shops, restaurants, festivals, and concerts.
Best time to go: Any time. Telluride is unique in that the town is brimming with activities during every season. But if you want to score a bargain, visit between March and April or October and November. Crowds are a bit more sparse and you can find cheaper hotel rates, according to U.S. News & World Report.
Expert tip: Get a Flatliner, Telluride’s signature drink. It’s an irresistible concoction made of espresso, rum, and Bailey’s. Just go easy on ‘em.
If you can, book a reservation for dinner at Alpino Vino. It’s a cozy Italian restaurant huddled about 12,000 feet in the mountains (making it the highest-elevation restaurant in North America, per Telluride.com). You’ll rumble up the mountain face in an enclosed Snow-Coach, and relish in a five-course prix fixe meal complemented by one doozy of a wine list and a crackling fire. Pure bliss.