Restaurants at Okemo
I wish I'd seen this question sooner! My husband and I spend our winters at Okemo so we're pretty familiar with the local restaurants.
Great sports bar and hang out for families and college kids is Cool Moose Saloon in the shopping center with Joe Jones, they have good burgers. The Kilarney Tavern has very good food (love the bangers and mash and the Verbacon burger), an a nice pub atmosphere. On Main Street is The Hatchery. They have a very creative menu, serve breakfast all day and lunch (great corn beef hash) - beware it's cash only. There's a Subway (you know what to expect), a Chinese Restaurant Chef Mei, and Wicked Good Pizza. On Main Street is also DJ's and Pot Bellys, good casual atmospheres and reasonable prices. Good food, but not necessarily outstanding.
Our favorite Italian restaurant is Panarello's on RT 103 outside of town. Sorta fancy, but not too fancy.
For a great pizza try The Pizza Stone in Chester, about 20 min ride from Okemo, but worth it for the thin crust pizza.
I'd highly recommend Harry's in Mt. Holly. We consider it a quintessential Vermont restaurant experience. I'd suggest reservations on the weekend. Another very creative menu and excellent food (you can find their menu online).
The only place I'd warn against is Cappuccino's, but it's not a place you'd take your son. We thought the food was just so-so and the atmosphere is horrible.
Hope you have fun at Okemo!
Just for the record, Cappucino's is no longer in business--in its place is a really great new eatery called "The Downtown Grocery," with a terrific chef-owner and a bold, adventurous menu. As to your burger recommendation: Cool Moose? Really? For a fraction of the price, DJ's, just down the street, does a much better burger with handcut fries. In my opinion, however, the best burger in town is served at Tom Koch's "The Loft," just adjacent to the Okemo base lodge. Tom grinds some brisket to mix into his burgers, and the results are succulent. Again, Tom handcuts his own fries, which is always preferable.
My brother loves Harry's, I think it's fine, but to call it the "quintessential Vermont restaurant experience" seems odd. It's kind of Asian influenced and a bit more inventive than what I think of as quintessential VT.
I second the recs for DJ's, love those baked stuffed shrimp.
Definitely first SEARCH what you're seeking on the board before asking a question. I myself just asked about food around okemo a few weeks ago....here's what I got (some promising sounding places):
p.s. make sure to hit the Waffle Haus (I think that's what it's called) right on the mountain for a fresh waffle. I saw them on the Travel Channel and being the Chowhound that I am, that was partly what motivated us to select Okemo for a trip we're taking in a few weeks.