There is not a ton of night life in winter park. Not like Summit County, etc. Wp is still more or less a spot on the road compared to more devloped areas. And that's ok with me cuz I am usually pretty blown from skiing at the end of the day.
Winter Park Pub on the north end of town is the local drinking hole.
Randi's Irish Saloon has good beer and food and sports on tv.
The Shed has some good mexican food. And beer.
There are bars/restuarants at Copper Creek Square in WP, though I have only been to the chinese joint for take out. I can't recall the name of the restaraunt on the east side of the road, across from Cooper Creek...but they will have the game on for sure.
Fraser has the Silver Creek or some such bar. It would be hard to miss.