There are lots of good winery's and breweries there although they cannot touch our Montana IPAs. Prarie Berry is in there and has a big parking lot. Get a cheese plate and sit on the porch. Just about a mile down from it is another place with a big parking lot and I can't remember the name but the wines have a motorcycle theme on wine naming. Then Naked winery. They are all decent wines a few odd ones. We do love Naked's Ramblin Red in the plastic bottle for "roughing it." I believe all three of those wineries and a couple of breweries are right in that stretch of road. Camp close and have fun...
Prarie Berry has some oddballs but fun to taste, three rednecks my fav. Their premiums are distinctly better. Naked's Vixen pretty good for fun. None of these are fantastic but are fun to drink wines and a great little wine tour. We bought land about five miles out of Custer for retirement. It is still relatively inexpensive but be sure there is proven water on any land you might consider in the area. We usually hit the Custer Naked Winery.
We either stay at the Big Pine Campground (nice wooded decent sites) when camping or the Super 8 (they take dogs) when just driving http://www.bigpinecampground.com/