Best events in

Jamestown

For events and things to do in Jamestown, KY, the local scene is defined by the seasons and life on Lake Cumberland. In warmer months, the energy revolves around boating and lakeside entertainment, while a quieter, small-town community spirit characterizes the rest of the year. Social life flows between the historic Jamestown Square, which hosts civic gatherings, and the bustling marinas that come alive with visitors.

• During peak season, an evening can start with lakeside dining at a marina before moving on to live music or a more relaxed community gathering on the town square.
• Family-friendly traditions are centered around Monument Square, home to annual celebrations like Lakefest and Christmas on the Square.
• The region's boating culture is on full display at major annual meetups like the Lake Cumberland Poker Run, which draws crowds to State Dock.