Windermere Fall Events That Have Become Local Traditions
When fall comes around, the events around Orlando start ramping up, and Windermere is no exception. Windermere's fall events calendar for 2026 includes the Windermere Garden Club Flower Show, Run Among the Lakes 5K/10K, Windermere Oktoberfest, and the Halloween Costume Parade & Hayride. These local events have become annual traditions for residents and visitors to celebrate the change of seasons.
What's Happening this Fall in Windermere, FL?
Windermere Garden Club Flower Show
This "Just for Fun" flower show will be celebrates National Constitution Day. The public is invited to see creativity through flowers and plants.
- Location: Windermere Town Hall at 520 Main Street.
- Date: Thursday, September 17 from 2:00 pm to 8:00 pm & Friday, September 18 from 9:00 am to 7:30 pm
- Free to the public
Pictured here is from the Fall 2025 Flower Show.
Windermere Run Among the Lakes 5K/10K | October 10, 2026
Windermere's 25th annual Run Among the Lakes takes place Saturday, October 10, 2026, beginning at Windermere Town Hall. The 10K starts at 7:10 a.m., followed by the 5K at 7:35 a.m.
The 5K is a run-or-walk option, and the 10K is a run-only event. Kids 7 and under can participate in the Kids Run. The routes extend throughout downtown and run along the lakes, as participants will pass three of the Butler Chain of Lakes: Lake Down, Lake Butler, and Lake Bessie.
- Location: The start and finish are located at the Windermere Town Hall on Main Street
- Date: Race Day is Saturday, October 10th
- Times: 10K Race begins at 7:10 am, and the 5K Walk/Run begins at 7:35 am
- Race Packet Pickup: Thurs & Fri, Oct 8 & 9 from 3:00 pm - 6:00 pm and Sat, Oct 10 from 6:00 am - 7:10 am
Register for the 2026 Windermere Run Among the Lakes.
Windermere Oktoberfest | October 2-4, 2026
Join Windermere Brewing Company for their 2026 Oktoberfest. Located at 111 W 5th Ave in Downtown Windermere, this event will feature German food and craft brews. This year's event will feature live music on Friday & Saturday, a stein-holding competition on Saturday, food trucks and more.
- Location: Windermere Brewing Company
- Dates: Friday, October 2 (4-9pm), Saturday, October 3 (1-9pm), Sunday, October 4 (2-7pm)
Windermere Craft Beer Fest | Canceled
The 2026 Windermere Craft Beer Fest has been canceled. This guide has been updated as of September 22, 2026.
Windermere Spook-Tacular Hayride & Costume Parade | October 24, 2026
Bring the family for the annual Halloween Costume Parade and Hayride. Kiddos will enjoy trick-or-treating at local downtown businesses along Main Street, join the costume parade, and play in bounce houses.
- Location: Downtown Windermere at the Town Hall
- Date & Time: Saturday, October 24 beginning at 9:30 am
Local Resident Pumpkin Carving & Potluck | October 25, 2026
A unique local experience for Windermere Town residents and their guests. Hosted by the Windermere Historic Preservation Board, join neighbors to carve pumpkins as a "BYOP" event (bring your own pumpkin & carving tools). In addition, enjoy a family-style potluck.
- Location: Windermere Town Hall
- Date & Time: Sunday, October 25 from 4:00 pm - 7:00 pm
What is Community Life Like In Windermere?
The surrounding community is just as important as the home itself. Is it active? Are there shops and services nearby? What is the vibe of the downtown? How would a local describe living in Windermere to a friend?
Windermere has a small-lake-town feel with brick-lined streets, towering Oaks with dripping moss, and a main street with cozy shops and dining options. That downtown experience also extends to the Windermere Golf Cart District, which connects the residents with local parks, businesses, and community events by golf cart. But what makes a town more than just a town? It's the people, places and events combined that make it special. Windermere is home to many weekly, seasonal, and annual events, and fall is a prime time for annual events.
Curious About Moving to Windermere?
Working with a local expert like Jeffrey Funk, who lives and works in Windermere, gives an insider perspective on the communities, homes, and lifestyle the area offers. For sellers, he knows the local market inside and out and believes that educated sellers = smart sellers.
Jeffrey & Renee Funk, co-founders of The Funk Collection, brokered by eXp Realty, have proudly called Windermere home since 2008 and have raised their family here. The team has over 25 years of experience serving buyers and sellers in Southwest Orlando with more than 500 5-Star reviews.
Jeff built RealtyInOrlando.com as THE source for living in Windermere. See available homes, explore 85 of Windermere's neighborhoods, find hyper-local market data, and see sold homes in each community.
If you're ready to start a conversation about buying or selling your Windermere home, schedule a call with Jeff.
Windermere Fall Event FAQ
What events are happening in Windermere in October 2026?
Windermere's October 2026 events include the Run Among the Lakes 5K/10K on October 10 and the annual Halloween Costume Parade & Hayride on October 24. Additional local events may be added throughout the season, so event details should be confirmed with the Town of Windermere or event organizer before attending.
When is Oktoberfest in Windermere in 2026?
Windermere Brewing Company's 2026 Oktoberfest takes place Friday, October 2 through Sunday, October 4 at 111 W 5th Ave in Downtown Windermere. Hours are Friday from 4–9 p.m., Saturday from 1–9 p.m., and Sunday from 2–7 p.m. The weekend will feature German food, craft brews, food trucks, live music on Friday and Saturday, and a stein-holding competition on Saturday.
When is the Windermere Run Among the Lakes in 2026?
The 2026 Run Among the Lakes 5K/10K takes place Saturday, October 10, at Windermere Town Hall. The 10K begins at 7:10 a.m., followed by the 5K at 7:35 a.m. and the Kids Run at 8:45 a.m. The event is celebrating its 25th year in 2026.
When is the Windermere Halloween Hayride in 2026?
The annual Windermere Halloween Costume Parade & Hayride is scheduled for Saturday, October 24, 2026, beginning at 9:30 a.m. at Windermere Town Hall.
Is the Windermere Craft Beer Fest happening in 2026?
No. The Windermere Craft Beer Fest scheduled for fall 2026 has been canceled.
Where are Windermere community events held?
Many Town of Windermere events are held around Windermere Town Hall and the downtown area, including annual traditions such as Run Among the Lakes and the Halloween Costume Parade & Hayride. Locations vary by event, so individual event details should be checked before attending.
Posted by Jen Durben on
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