Hermann, MO has quite a few wineries, a few distilleries, restaurants and places to stay. New Haven, MO isn't too far from there - Pickney Bend distillery is located there and they have a glassblower. Though with covid and winter I'm not sure what is open. During the summer you can buy a trolley pass to go wherever you want.
Traverse City would be great - not so much in winter.
The Twin Cities & KC - plenty of places to fit the drink/food criteria
Bentonville & Rogers, Arkansas might be an area to try. At least it should be warmer there. LOL.
This is one way I help figure out where to go for weekend trips, etc:
https://www.oalley.net/app/. You put in your location and how long of a drive you'd like to do.
Here's a website I found with ideas for breweries and wineries:
http://www.winecompass.com