We went to Telluride for a friend’s 40th a couple weeks ago, so I wanted to share everything we did. Telluride and Aspen were both new to us this winter, and it’s been fun trying out new mountain towns. I will say, though, the mountains are rough on me! My Oura ring was trash on both trips and honestly both places made me feel pretty shitty (though I was much better in Telluride, likely because I took this altitude drink the entire time). But maybe I’m not cut out for the elevation?? Anyways, it seems like a lot of you are heading to Telluride soon or want to plan a trip there, so here’s what we did, what I wore, etc.


Overall, Telluride was very chill. Think laidback, Western vibes, and saloon-ish style mountain town. It was much less of scene than Aspen. As for what I wore, I linked everything here. My friends and I were the most overdressed pretty much everywhere we went, so heads-up for packing purposes.


We stayed at the Madeline in Mountain Village, which is more of the ski-in / ski-out part of town. It’s on the other side of the mountain from the town of Telluride, but it was perfect for us since the guys were snowboarding. We went into town each day and the gondola ride in was GORG and easy to grab from Mountain Village. As for the hotel, it was cute and I’d stay there again – though they definitely could use a spa remodel.


In between laying low and a spa day, here’s where we ate, drank & did:

Timber Room – This was one of the restaurants in our hotel. We booked it for a full dinner but it’s more of an aprés ski / sharing food situation, so I’d suggest it for drinks and apps instead of a sit-down meal.

Allreds – We tried to grab drinks here right when they opened, but it was too crowded, so we didn’t get in. Instead, we took advantage of the gorgeous views from this spot on the gondola / top of mountain. We said next time we’d bring our own drinks up and skip the wait at Allreds – the view is incredible and worth the stop!

Sheridan Hotel – We were told this was a Telluride staple so we grabbed a drink here before dinner one night. Very saloon, old school, local feeling and loved it.

Floradora Saloon – Another Telluride staple where we had dinner one night. Again casual but cute and the food was pretty good.

Cosmopolitan – This was the nicest dinner we had and the only place we weren’t totally overdressed for. This was probably my favorite food of the trip, so don’t miss it. They had a great wine list as well.

Tomboy Tavern – Depending on when you go, this is a fun aprés ski spot with casual eats. You have to order the cookie skillet dessert!

Altezza Restaurant – We came back to this spot a couple times only because it was convenient and the views were beautiful. The food and vibe were whatever but it got the job done for breakfast / lunch.

Shopping – This was a total fail, which was probably for the best. Unlike Aspen, the town of Telluride didn’t have much outside of a couple western stores and lots of touristy spots, so don’t expect to shop much.

Sleigh ride – We did this through Telluride Sleighs & Wagons and it was a highlight of the trip! They drive you into the mountains and bring you to a sleigh ride, fire and smores, and a cute little yurt with hot drinks. The views were insane and I highly recommend!


We flew into Montrose on the way there, and then it was 1.5 hour drive to Telluride. This made for a long travel day since it was two flights and a drive from SD, but apparently, it’s a lot more likely to get in /out of Montrose vs. Telluride airport. Paul and I flew out of Telluride when leaving which was easy but the runway is terrfying. We basically booked two tickets on the way home and kept an eye on conditions to see if we could fly out of Telluride (vs. Montrose) and we got lucky.

DM if you have any other questions & LMK if you want to write out our Aspen itinerary as well.