Columbus Day weekend, October 9-12 this year, is one of my favorite moments in Lake Wales. The Florida summer heat finally loosens its grip, the live oaks go golden at dusk, and the whole community steps out to celebrate the start of fall. It is a long weekend built for slowing down, and I have watched this little ridge-country town throw its arms around it year after year. That is the Lake Wales I fell in love with, and the one I am proud to help people call home. Here are the verified fall events happening in and around Lake Wales this season, so you can plan your long weekend around the very best of our community.
The Columbus Day weekend lineup, October 9-12
The holiday weekend itself is packed with laid-back, family-friendly ways to get out and enjoy the ridge. These are the events we have confirmed right on and around the long weekend.
Lake Wales Downtown Farmers Market
Start your Saturday at the Lake Wales Downtown Farmers Market, held at Market Square (20 N. Market Place). It runs on the second and fourth Saturdays of the month, which lands it right on Columbus Day weekend, October 10, from 9 a.m. to 1 p.m., with a second date on Saturday, October 24. It is free to browse, with local produce, baked goods, crafts, and live local flavor in the heart of the historic downtown. See the current schedule on the Lake Wales Main Street events page.
Westgate Saturday Night Rodeo
For a true Central Florida evening, head about 30 to 40 minutes south to Westgate River Ranch Resort and Rodeo (3200 River Ranch Blvd., River Ranch, FL 33867). The rodeo runs every Saturday night, and the October 10 show goes from 7:30 to 9:30 p.m., closing with the ranch's street party and country-western fun. It is a recurring favorite that never gets old. Details are listed on Visit Central Florida.
Harvest Holler Corn Maze and Pumpkin Patch
Fall weekends call for pumpkins, and Harvest Holler Corn Maze and Pumpkin Patch at 950 Tavares Rd., Polk City, FL 33868, is a short drive from Lake Wales and worth taking. Its 2026 fall season runs September 18 through November 15, open Fridays 4 to 8 p.m., Saturdays noon to 8 p.m., and Sundays 1 to 5 p.m. (Sunday hours can vary, so confirm the day before you go). You will find a corn maze, tractor hayrides, farm animals, and pumpkin picking. Check harvestholler.com for the full fall schedule.
Bok Tower Gardens: a season of fall events
Bok Tower Gardens at 1151 Tower Blvd. is the crown jewel of Lake Wales, and this fall it has three reasons to visit again and again. Mark these on your calendar:
Stories in Stone: Primal
Through January 3, 2027, Bok Tower Gardens hosts Stories in Stone: Primal, a garden exhibit of monumental outdoor stone-balancing sculptures by artist ZOTO (Adam Conard), open daily from 8 a.m. to 5 p.m. It is included with regular garden admission: free for members, $20 for adults, $10 for ages 6 to 17, and free for children 5 and under. See the exhibit page for details.
Rootstock Fall Plant Sale
October 3, from 9 a.m. to 4 p.m. at the Visitor Center Picnic Area, opens Florida's fall gardening season with more than 30 plant vendors, hayrides, and live music. October is when Florida gardeners finally plant again, so this is the perfect kickoff, and it is included with garden admission. See Bok Tower Gardens' events page.
Boktoberfest: DeLeon Live on the Oval
Bok Tower Gardens celebrates October with Boktoberfest: DeLeon Live on the Oval, Friday, October 16 at 7 p.m. on the Oval Lawn. A three-generation German Oktoberfest band is paired with German food and brews under the garden's evening lights. Confirm tickets and details on the Boktoberfest event page.
Historic downtown: wine walks and heritage
Lake Wales' historic downtown is the soul of the community, and October brings several signature events there you will not want to miss.
Wicked Wine Walk
On Friday, October 16, at 5 p.m., Historic Downtown Lake Wales turns into a 21-plus evening of curated wine tastings, character photo ops, a scavenger hunt, and treats, with costumes enthusiastically encouraged, running until about 10 p.m. Tickets went on sale September 14 at 8 a.m., so check availability soon. Grab yours through the Wicked Wine Walk page on Lake Wales Main Street.
Lake Wales Live: Hometown Sounds
On Friday, October 23, the free Lake Wales Live concert series returns to Market Plaza (20 N. Market Place) from 5 to 8:30 p.m. featuring the band Hometown Sounds, with food and drink vendors typically on hand. The series is produced in partnership with the City of Lake Wales, Lake Wales Main Street, and the Lake Wales Arts Council. Details are on the City of Lake Wales signature events page.
50th Annual Pioneer Days Festival
One of the community's proudest traditions, the 50th Annual Pioneer Days Festival, presented by the Lake Wales History Museum, runs Saturday and Sunday, October 24 and 25, from 10 a.m. to 4 p.m. at Lake Wailes Park (33 N. Lake Shore Blvd.). It is free, with historical reenactments, pioneer camps, artisan crafts, live music, a car and tractor show, and a pumpkin patch. The kickoff, Beers with Pioneers, happens Friday, October 23. Learn more on the Lake Wales History Museum's Pioneer Days page.
Halloween Spooktacular Bash
Downtown Lake Wales closes out the month with the family-friendly Halloween Spooktacular Bash, planned once again for 2026. This free event features a Trick-or-Treat Trail, entertainment, displays, food, and vendors in a costumed, walkable downtown. The exact date is announced closer to the season, so watch the City of Lake Wales signature events page for the final lineup.
Make Lake Wales your home base
There is a reason the calendar here stays this full from October to spring: Lake Wales is a community that genuinely gathers. Whether you are visiting for the holiday weekend or daydreaming about trading a crowded suburb for the ridge, the lakes, and the oak-shaded downtown, this is a wonderful place to put down roots. If you are considering making Lake Wales home, I would love to talk. Tell me about your situation and what is important to you in a community, and we will find your place in it. Call us at 863-270-2706, email Michelle@MCCollectiveRealEstate.com, or request a consultation at mcrequest.com. Here to help whenever you're ready.
