A hidden gem right down the road from the Litchfield Inn. They give a great tour/tasting. The black label bourbon is a favorite of James and "Papa K" (Dana's dad)!
A beautiful short hike can be had here! There is a parking fee on weekends for CT non-residents.
The closest major casino is MGM Springfield (MA). Others in CT at more of a distance are Foxwoods and Mohegan Sun.