- Bridal Fair: Second Saturday in April Annually at the Village Barn
- Fairy Garden Tours, Annually, Saturday before Mother’s Day, throughout the Village
- Secret Garden Plant & Art Sale, 10:00AM to 3:00PM, Saturday before Mother’s Day, at The Chocolate Garage
- Vintage Market & Antique Shoe, Annually, Saturday after Mother’s Day in the Village Barn and Park
- Car Cruize & Porch Pickin’ Music on Main Street, Saturday BEFORE Father’s Day.
- Picker’s Rendezvous – Last Saturday in June at Pattie’s Pickens, South end of Caledonia on Hwy 21
- Blackberry Festival, last Saturday of July at Caledonia Vineyard off Webster Road
- Porch Pickin Music on Main Street, The Saturday after the third full week in August
- Caledonia United Methodist Church annual Church Auction, Third Saturday in September
- Junk-A-Rama + Porch Pickin music on Main Street, third Saturday in September.
- Rowe Crop Farm’s Pumpkin Patch & Corn Maze Opening Day, third Saturday in September.
- Pumpkin Fest, annually, second Saturday in October, Starting with a parade down Main Street at 10:AM, Main event in Village Park and barn, many free things for children to do, events throughout the Village 10:00AM to 4:00PM, Come join us for a day of fun.
- Caledonia United Methodist Church annual Chicken and Dumpling Dinner, third Saturday in October.
- Witches Day 3rd Saturday in October in the Chocolate Garage at 400 S. State Hwy 21, call 573-315-0257 for reservations and more information.
- Hocus Pocus – 4th Saturday in October through the Village
- Witches Drinks at The Twelve Mile Creek Emporium 4PM to 8PM.
- 5K Pumpkin Run/Walk – First Saturday in October
- Last Day of Corn Maze & Pumpkin Patch – First Saturday in November
- Christmas Open House & Chocolate Walk – Friday and Saturday BEFORE Thanksgiving AT ALL PARTICIPATING BUSINESSES.
- Goose Creek Farm’s Christmas Trees Opening Day – Friday after Thanksgiving
- Village Christmas Market & Cookie Walk – First Saturday in December Throughout the Village.