For food the Mackenzie River Pizza company would be my pick. Bert & Ernies tavern and grill has also been recently renovated and has live music on weekends, it's another good option.
Another place I'd recommend is the Stein Haus on 1st Ave N - It's not much to look at but they have a pretty awesome selection of Montana micro brews (20+). Sampling the local beer is a must for any trip right?