vail, aspen, telluride, steamboat
I headed to Vail once a year for the past 10-12 years, but have also ski'd Aspen, Telluride and Steamboat. All are great IMHO. As you are coming so far, probably Vail or Aspen are your best bet to get as much in for one trip.
Vail is majorly easy to get to, has a huge mountain and has great restaurants / apres ski. See below for a list of my favorite things.
Aspen has a great town. I'm not sure I like the bus that shuttles between the different mountains, but it's not bad. Definitely stay in Aspen, not at Snowmass. Snowmass is more of a family type place and not as much to do at night. I'd like to go back simply because I've not explored this area enough. (although one type of downside, I wasn't too comfortable in the Prada store. While I enjoyed browsing - I thought I was being measured by a few other customers. It's kind of like - hey, who cares - it's a public place.)
Telluride might just be my personal favorite. The scenery is simply breathtaking, the snow is incredible and I love the runs. It's the best 'western / mining town feel'. Stay in the town of Telluride, not up in Mountain Village. Again, see below for my list of favs to do. More tips below.
Lastly and certainly, not leastly - Steamboat. I've only been here once, but absolutely loved it. We stayed a one of the hotels right at the base of the lift (ski in / out, but reasonably priced). I think it was the best western ptarmigan inn. They had an outdoor pool / hottub combination and would serve us pitchers of beer while we were in the hottub for apres ski.
I really enjoyed the mountain as well and thought the snow quality was tops. also more tips below.
Below are some things you may enjoy...
There are a number of excellent restaurants and some other fun things. Often on Wed evening, they have music on one of the streets. I'm not sure if this is all season or just the time of year when we go or not. Check the website. There are also about 4 places for fun entertainment. The Red Lion has a lively apres ski w/ reasonably priced food. It's sort of a yuppy college feel here. The crowd gets involved as they do at most of these I'll list.
The Club can be entertaining as well - look for when Steve ???? is playing. I can't remember his last name, but he is a fixture in Vail during ski season. Just ask around. Word of warning. He's not pure 'music'. He does sing and sing well, but he's also doing shots and having an 'interesting' dialog with the crowd. It's a bit edgy and may or may not be your thing. Personally, I think he is a huge riot and he usually gets some 'rich old bastard' to buy a round of drinks for the bar. Lot's of sing-a-long here as well. Probably only need to hit this once for your fill.
Mickey's in the Vail at Lodge can be a nice alternative if you are looking for a classy evening of piano music. It's a small spot - very cozy, but get's crowded. A bit of an older crowd. More a glass of scotch or wine vs the beer and shots crowd.
I also like Pepi's. It's a restaurant with a bar on the side. Again, classy sing-a-long. A bit more adult than the Red Lion. This has a bit more of a european ski resort feel. Great food if you like Austrian or wild game style food.
Other restaurants I enjoy... Cucina Rustica in the Lodge at Vail. This is one of my two fav italian restaurants in town. Before they changed chef's last year, they had a magnificant antipasta bar. I'm sure the new chef was getting major pressure to bring it back. I'll find out this Dec...
The Flying Burrito in Lionshead is a great spot for breakfast on your way to the gondola. Reasonable prices, good food. Small place and the service can be a bit slow, so give yourself a bit of time.
Campo di Fiori is a really nice spot. It's not as mainstream and a little awkward to find, but I think it's got a nice romantic and relaxing atmosphere. The food works as well. Have a nice port for dessert.
Sweet Basil's is a high-end, nice spot, reservations necessary.
Back on the economical end for breakfast, there is a local's spot in the west side of Lionshead past the gondola. If you like a major breakfast this is the place. Huge portions of eggs, pancakes, whatever breakfast you want. I can't remember the name and don't know if it was affected by the current construction in Lionshead - but what a great find.
Overall, I like to spend more time in Vail Village than Lionshead in the evening. We usually go up/down the mountain out of Lionshead (thus breakfast in Lionshead).
At the base of the mountain, we found a little Irish pub that had a GREAT irish music band. We didn't go looking for as much music elsewhere.
One of the really special NOT to be missed things in Steamboat is a trip at night to the hotsprings. Now there are 2 sets of hotsprings. One is in town in a building with limited atmosphere. Do not go here. The other requires buying a ticket at the base of the mountain w/ a reservation to take a shuttle up a canyon along the mountain. After a short ride (20 mins or so), you end up at the end of a dirt road and it's extremely dark. Your driver will escort the group down a set of steps by flashlight. You arrive at a set of 3 natural hot springs of different water temps. There are tee-pees to change into a bathing suit, or you may go 'au naturale'. No need to let this intimidate you. It's extremely dark so you shouldn't get embarrassed. You can take a beverage with you (I'd recommend no glass) if you like as well. The night I went was soooo incredible. Not a cloud in the sky and it was as if someone had attached a lightbulb to every star in the sky. Really an amazing night. If you really want to treat yourself, you can also have a massage in the woods where they integrate the water from the hotsprings into the experience. It's a sexy place for a couple and also fun for a group of friends!
Personal fav. Stay at the Ice House in Telluride. It's at the base of the gondola and 2 blocks from town.
Not a big apres ski scene, but great restaurants, a few nice bars and classy shopping.
Fav restaurants: Cosmopolitan (make sure to make a reservation BEFORE you arrive in Telluride - they book out a few weeks), Honga's Lotus Petal - great sushi / asian food (also need a reservation), and BluePoint / Noir Bar - I LOVE this place (it's a great atmosphere casual metropolitan if you will w/ excellent food / the bar has that great NYC lounge feel).
On the main street there are a couple of bars to hang at - a local's place that I think is named 'bar', but I could be wrong - they have pool / darts and a very casual feel. Also the New Sheridan hotel has a classy bar complete w/ fireplace and pool tables in the back.
No need to go to Mountain Village at night IMHO except to ride the gondola up and down on a clear night to see the moon light against the canyon!
Have an EXCELLENT trip!