Little Bear Inn

Jordan Cabernet Sauvignon — $100 bottle (half-price on Wednesdays)

Jordan normally hits the list at the top of the bottle range, but on Wednesday half-price nights it becomes one of the better steakhouse Cab deals in Cheyenne. A wine this recognizable at half its menu price next to a proper cut of beef is hard to argue with.

Washington State selections

Most tables reach straight for the Caymus and call it a night, but whatever Washington bottles are hiding on this list tend to fly under the radar. Walla Walla and Columbia Valley producers often deliver serious red fruit and structure at a fraction of the Napa hype tax — worth asking the server what's pouring from the Pacific Northwest.

Meiomi Pinot Noir

Meiomi is a fine grocery store Pinot, but you're paying restaurant markup on a wine that retails for $15–$18 anywhere. Unless it shows up on a Wednesday deal, there's no reason to order it here when the red meat on your plate is calling for something with more backbone.

Caymus Cabernet Sauvignon + Surf and Turf

Caymus is ripe, bold, and unsubtle — which is exactly what you want sitting next to a slab of steak. The surf element softens the pairing just enough that the wine's fruit doesn't steamroll everything on the plate. It's not a sophisticated match, but it's a satisfying one.