About

Happy Jack's Winery is a small farm winery located in Breckinridge County at Rough River Lake, owned and operated by Jack and Tee Pleasant, a retired police officer and nurse originally from Louisville who turned their hobby into a business after moving there in 2021. They specialize in small batch wines, including fresh fruit wines, catering to all levels of wine drinkers from novices to experts. The winery offers on-site tastings, private events, farmers markets, and participates in local events with a focus on community and serene country settings.

Small batch wines Fresh fruit wines
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Photos
Winery scene Exterior view Award nomination pic Owners or people Event or venue Winery activity
Awards
Nominated as one of Kentucky’s top 3 Wineries
Upcoming Events
Hardin County Farmer’s Market
Saturday, April 11, 8am-12pm EST
Elizabethtown, KY, 200 Peterson Dr.
Wine Tastings at Big Mouth’s Restaurant
Sunday, April 12, 12-4pm CDT
14033 Falls of Rough Rd
Spring on the Square
Saturday, April 25, 9am-2pm CDT
Main St in Hardinsburg with vendors, food trucks, live music
Live Music at Happy Jack’s Winery
Saturday, April 25, 5-8pm CDT
Michael Keys, part of Sippin’ & Songs Series
HJW 3rd Annual Cruise In
Saturday, June 6, 12pm-close CDT
Vintage cars, vendor booths, food trucks, live music
Latest News

Nominated as one of Kentucky’s top 3 Wineries by Kentucky Living; new Sippin’ and Song Series for 2026; upcoming events including Cruise In and Wisdom, Women and Wine.