A List of Fall Events in Owensboro

Here in Owensboro, we celebrate Fall in all the best ways. Whether it’s a festival, trick-or-treating, or a day spent among the sunflowers, we’ve got it all. And here’s a list of what you can look forward to! 


Reid’s Orchard Apple Festival 


The Apple Festival will run for two days this year on October 22 and 23 at Reid’s Orchard. You can go pumpkin picking, enjoy rides at the carnival, eat all the apple-flavored treats you can imagine, and shop from tons of vendors at this family-friendly event. The only cost to attendees is $5 for parking. 


Reidland Play Area


Also held at Reid’s Orchard, the Reidland Play Area is a great way for families and kiddos to celebrate fall in all its beautiful glory. You can enjoy a corn maze, the famous Apple Slider slide, duck races, Bella’s Barnyard, inflatables, train rides on the Apple Express and even go apple and pumpkin picking at this venue. 


Sunflower Experience


Trunnell’s Farm Market is hosting its annual Sunflower Experience for all ages through the month of September. You can graze through a field of more than one million sunflowers, pick from the pumpkin patch, enjoy over 35 different attractions, visit the animal barnyard and eat delicious apple cider donuts and slushies. You can get tickets right here for $27.99. 


Fall Farm Experience


Trunnell’s will also host its Fall Farm Experience October 1-November 4, which includes a number of events to get you right into the fall spirit. Wine Your Way Out will be held on October 1 and 7, where you and your favorite people can sip on wine as you wind your way through a corn maze, sit by the bonfire, and listen to music. 


Trunnell’s will also hold the Great Pumpkin Glow Fest on October 8, 14 and 22, and the Adults Only Fall Fest on October 15. Even more, you can bring the entire crew to Family Flashlight Night on October 21, and the adults can celebrate Halloween with Trunnell’s Hallo-Wine Bash & Brew Fest on October 29. 


Pumpkin & Pickle Festival


Held at the Cottage Farm Stand & Baking Co., the Pumpkin & Pickle Festival will be held for two days on October 1 and 2. Enjoy tons of pumpkins, delicious pickle-flavored foods, an amazing pumpkin patch and a corn maze at this fall-themed event. 


Farm-to-Table Dinner


Cecil Farms and Hill View Farms will collaborate to bring you a fantastic farm-to-table dinner with all the best meats and produce farmed and harvested here locally. Enjoy live music and a sunset dinner overlooking hundreds of acres of beautiful western Daviess County farmland. This year’s event will be held on September 22 from 6-9 p.m. and tickets can be purchased here for $75. 


Fall Farm Market


Hayden Farms will hold its annual Fall Farm Market on September 18 from 11 a.m.-4 p.m. Grab lunch or an early dinner from some of the many wonderful food vendors, and shop for pumpkins and fall decor from shopping vendors as well. Play yard games with the family and have fun on hay rides and a flower patch. Parking is $5 per car. 


Trail of Treats


Downtown Owensboro is once again kicking off Halloween the right way with its annual Trail of Treats event, hosted by the City of Owensboro. Held on October 27 at 5:30 p.m., this family-friendly event will bring you a night of trick-or-treating, character appearances and special photo opps. The event is free to the public, so be sure to bring a bag for all that candy! 




Enjoy live music all day and shop from independent artisans and businesses as you sip on brews and take in the beautiful fall weather. Events, such as a stein holding contest, can be enjoyed by the adults, and several breweries will be participating in this year’s downtown event. Bloktoberfest will be held on October 22 from 2-8 p.m. 


Holiday Market


The Owensboro Regional Farmers’ Market will hold its annual Holiday Market on November 4 from 8 a.m.-2 p.m. This is the Farmers’ Market most-attended event of the year, and you can shop from all the local farmers and vendors imaginable at this one-day event. You can also enjoy the Farmers’ Market during the month of September on Tuesdays and Saturdays from 8 a.m.-noon.