Day 1: Friday Arrival
Afternoon
Fly into Montrose Regional Airport if you're coming from out of state — plan 75 minutes by car or shuttle. If you're driving from Denver, Albuquerque, or Salt Lake, plan for a 6–7 hour road trip (or more in a winter storm). Check in at your hotel, Airbnb, or Mountain Village condo. If you're staying in town, you can walk everywhere. If you're in Mountain Village, the free gondola connects you into Telluride in 11 minutes. Just remember to stay in the car at the top.
Evening
Grab a casual dinner at Brown Dog Pizza for Detroit-style pies or La Cocina de Luz for incredible Mexican food (careful with the top shelf margaritas if you are coming from sea level). Or head to The Grand or The National for upscale mountain cuisine. If you've got energy left — and seriously be careful with the hangover and dehydration at 10,000 feet — stop by New Sheridan Bar.
Day 2: Saturday Adventure
Morning
Fuel up with coffee and breakfast burritos at The Butcher & The Baker or Baked in Telluride. For just coffee, I recommend The Telluride Company. Then get outside.
- Summer/Fall: Hike Bear Creek Trail — a mellow 5-mile round-trip to a waterfall right from town. Or tackle the Sneffels Highline, a tough but jaw-dropping 13-mile loop. Start early to avoid afternoon monsoons.
- Winter: Take Lift 4 from Mountain Village or Lift 7 from town, then head over to Lift 5 for a blue square warm-up.
Afternoon
Lunch on-mountain if you're skiing (Goronno's or Giuseppe's), or try La Cocina or Oak in town. Spend the afternoon wandering the historic district. If bored skiing, go get drinks during happy hour at Allred's.
Evening
Dinner at 221 South Oak — an institution run by former Top Chef Eliza Gavin, with a dedicated vegetarian menu — or Floradora on Main Street. Cap the night with live music at the Sheridan Opera House (fancier) or Fly Me to The Moon (grungier).
Day 3: Sunday Wind-Down
- People watch from The Telluride Company or Butcher & Baker
- Stroll or cross-country ski the Valley Floor
- Sneak in a few more ski runs if it's winter
Pack up and start the journey back. You'll leave tired, a little sore, and already scheming your next trip.
Pro Tips
- Skip the rental car — in town or Mountain Village, you won't need it
- Book early: lodging fills fast for festivals and ski weekends
- Altitude matters: hydrate constantly, and watch the alcohol on night one