TR's Tavern, located at the back of Theodore's Dining Room in the Rough Riders Hotel, is a great option in town. It's open (in the off season) when the restaurant might not be, but it's only got about five or six tables, plus maybe a dozen seats at the bar. When we were there, we had no trouble getting a table at dinner time, but one night the bar was full of the performers from the Medora Musical, so it was a bit rowdy. Other guests at the hotel mentioned some difficulty in getting a table when the restaurant wasn't open, so it's worth it to check.
The Tavern has two local beers on tap (both of which you can taste for free), and a decent sized wine menu in addition to the bar menu (with good options from sandwiches to salads). You can also order from the full restaurant menu (which I did one night, and the fettuccine alfredo was delicious and not to overly sauced).
Tess, the server, was very helpful with hints about where to go in Theodore Roosevelt National park, in terms of getting the best views and the most animals. She also served us quickly when we needed it and let us just sit and hang out when we wanted to.
Definitely worth a stop! The only reason I didn't give it five stars is that the menu wasn't quite as varied as I would have liked.
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