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, plus a few more fall favorites beyond it.
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 Saturday Night Rodeo runs every Saturday night, and the October 10 show goes from 7:30 to 9:30 p.m., with bronc riding, barrel racing, and calf roping on the program. Tickets for resort guests run about $35 for adults and $30 for children, with lower pricing for resort owners, and the season continues every Saturday through the fall. Details are listed on Visit Central Florida.
LEGOLAND Brick-or-Treat
About 25 minutes northeast in Winter Haven, LEGOLAND Florida Resort (1 Legoland Way) turns into a Halloween wonderland each fall. Brick-or-Treat is on the calendar for Columbus Day weekend, Friday through Sunday, October 9-11, plus the weekends of October 3-4, 16-18, 23-25, and 30-31, with trick-or-treating, costume fun, and Halloween shows included with regular park admission. The 2026 season runs on select dates from September 5 through October 31. See the Brick-or-Treat event page for the full lineup.
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 noon to 5 p.m. (some pages list 1 to 5 p.m. on Sundays, 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
From October 2, 2026 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, a hayride through the Pine Ridge Preserve from 10 a.m. to 1 p.m., and live music on the Terrace. 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: arts, 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.
Florida Narratives: Stories in Folk Art
Thursday, October 1, the Lake Wales Arts Center (1099 State Road 60 E) opens a major exhibition, Florida Narratives: Stories in Folk Art, with a reception that evening. The show explores the diverse stories, traditions, and lived experiences that have shaped Florida through the work of folk and self-taught artists. See the Lake Wales Arts Council exhibitions page for hours and the closing date.
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 at roughly 20 downtown locations, character photo ops, a scavenger hunt, and treats, with costumes enthusiastically encouraged. The evening runs 5 to 9 p.m., and only 200 tickets are sold, so check availability soon. Tickets went on sale September 14 at 8 a.m. Grab yours through the Wicked Wine Walk page on Lake Wales Main Street.
Lake Wales Live
The free Lake Wales Live concert series brings live bands to Market Plaza (20 N. Market Place) on select Friday evenings in the fall, 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, and the fall 2026 dates and performers are being announced now. 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, set for Friday, October 30, from 5 to 9 p.m. at Downtown Market Plaza (20 N. Market Place). This free event features a Trick-or-Treat Trail, entertainment, displays, food, and vendors in a costumed, walkable downtown. It is organized by Lake Wales Main Street and listed on the City of Lake Wales calendar, so watch the Lake Wales Main Street events page and the City of Lake Wales calendar for the final lineup.
Spooky season at the ranch
Our resort communities know how to do fall too, and Westgate River Ranch goes all in. The Haunting of River Ranch runs Friday and Saturday nights from October 2 through October 31 (October 2, 3, 9, 10, 16, 17, 23, 24, 30, and 31), with a final night on Friday, November 6, at Westgate River Ranch Resort and Rodeo. Expect the Haunted Stables Experience, a haunted hayride, a haunted playground, spooky games, scare zones, and Halloween-themed food and drink. Recent seasons have priced entry around $10 for the public and resort guests, with the hayride ticketed separately; confirm current hours and pricing on the Haunting of River Ranch page.
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.
