Monterey Fair | Fifty Years of Memories

By Vanessa New Willhoite

Sweet Owen Contributor

Noel Red True

It’s hard to believe that the first Monterey Fair was fifty years ago!  What began in 1976 as a gathering of local artists and craftspeople has grown into a celebration of community, history and hometown pride. The original vision was simple: invite people to Monterey to experience handcrafted art, good food, live music and fellowship while showcasing the unique character of  the town.  Nearly fifty years later, that spirit remains at the heart of the fair.

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As the sun rises over the river hills, vendors begin filling the town with handcrafted  treasures, homemade treats and familiar smiles. Before  long, the aroma of burgoo drifts through town, music fills the air and old friends who haven’t seen one another in years stop in the middle of the street to catch up. Children laugh as they play old-fashioned games while grandparents watch with memories of doing the very same thing decades ago.

This year’s fair will be held Saturday, October 3, beginning at 10:00 a.m. Visitors can spend the day browsing handcrafted vendors, enjoying delicious foods, listening to talented local musicians and visiting with friends and neighbors.  The parade starts at noon. The ever-popular cornhole tournament begins at 1:00 p.m.  The traditional burgoo will be ready around  2:00 p.m.  Children can enjoy the playground, field games, the corn pit and other activities.  Don’t forget to stop by the silent auction before bidding closes at 4:00 p.m. As evening settles over Monterey, the celebration continues with the beloved street dance from 7:00–11:00 p.m. featuring The Killin Time Band.

If you were fortunate to experience some of the early fairs, you may remember decorating your bicycle for the parade, cheering on turtle races, watching the frontiermen co

me through town firing their long-rifles or dancing in the street long after sunset. Perhaps you remember Red True’s amphibious duckboat. If you visited Monterey at other times, you may remember playing croquet in the park during the 1970s, or spending summer afternoons at the old Monterey beach before the river eventually reclaimed it. Others remember basketball and volleyball games in the park, browsing candle shops and pottery studios, or simply sitting on a porch visiting with neighbors.

While the town itself has changed over the past fifty years, the purpose of the fair has never really changed. It’s still about celebrating handmade craftsmanship, preserving local traditions and creating new memories for the next generation. The faces may be different, but the welcoming spirit that inspired those first organizers in 1976 still greets every visitor who comes into Monterey.

Whether you’ve attended every fair since the beginning, grew up in Monterey, or are planning your very first visit, we invite you to spend the day with us. Slow down, reconnect with old friends, meet new ones, enjoy the music, taste the burgoo, browse the handmade crafts and experience a piece of Kentucky that still feels wonderfully unchanged.

Join us this October as we celebrate 50 years of memories—and begin making the next fifty.

For additional information, visit the Monterey Fair Facebook page and look for the 2026 Monterey Homecoming Fair event. We’ll see you in Monterey!