I think you have made a great choice in coming to Okemo-we may not have the most challlenging terrain but we have huge snowmaking capacities and top notch grooming! There are several choices for dinking and dining depending on what you are looking for.
The Loft-this is the bar near the base lodge on the access road.This place is a real dive.This is where alot of the locals and instructors hang out.It can be kinda roudy but fun.The owner does most of the cooking and the food is great.They serve typical bar food and lots of it!! Burgers,nachos wings etc.
Archie's-bottom of the access road across the street in the strip mall.Has a bit of a sports bar feel and a large dining room. Alot of families go here(there is a small arcade) This is a steakhouse with salad bar,but you can also get burgers and fries.
DJ's-located in Ludlow heading south on 103-Again another steakhouse-a step up from Archies. If it is really crowded the bar is really small and gets really cramped in there.The food is pretty good and has good size servings-steak chicken fish type of place also has a salad bar.
Sams-located on the outskirts of Ludlow heading south.Yet another steakhouse but alot more ambience.The bar is rather nice with couches and soft chairs.They also have a fireplace and sometimes someone playing the piano.Maybe a bit more expensive than the previous two.I used to go here alot-nice place.
Harry's-located on 103 headed north near Mt Holly-this place gets my vote for the more unusual fare.Alot of their food has an Asian twist to it-Has a large menu-not real fancy but fun.
Coleman Brook Tavern-really nice ambience and a nice menu.I have only eaten there once a ways back.Since then I have heard mixed review(located at the base of Jackson Gore)about their food-Just outside the dining room is the lobby of JG which has a nice bar comfortable couches and a really nice fireplace-a good place for a quiet drink.
There are two new Italian restuarants-Panerello's which is right before Sam's(the owner of sams owns this place too)The other is located on 100N but I don't know the name.
As far as the instruction goes............ Okemo holds many training clinics throughout the year and all the pros are urged to attend. We have many L3's along with gobs of L2's many with 20 or so years of teaching experience.We offer a variety of programs for all levels of skiing.If you need some help here feel free to pm me and I will respond promptly! http://okemo.com/okemowinter/learning/index.asp
Hope I was able to help!