"We would rather make the difficult decision to cancel than to compromise for sub-par." The volunteers behind the Windermere Craft Beer Fest wrote that line in their September letter, which pulled the October 17 festival off the town's fall schedule.
Nine days later, Windermere Brewing Co. announced its own beer fest for that same Saturday at the brewery, 111 W. Fifth Ave. The rest of the month follows the same pattern. Each October Saturday in Windermere is held up by someone already based downtown: a town committee, the Public Works crew, the Main Street storefronts, or a brewery on Fifth Avenue. Knowing who runs each event tells you what to expect from it.
The Month at a Glance
- Saturday, October 10. The 25th Run Among the Lakes 5K and 10K at Windermere Town Hall, 520 Main Street.
- Saturday, October 17. Windermere Brewing Co.'s Backup Beer Fest, noon to 4 p.m., 111 W. Fifth Ave.
- Saturday, October 24. The Halloween Costume Parade & Hayride at Town Hall, starting at 9:30 a.m.
- Saturday, October 31. The annual Sleep in Heavenly Peace bunk-bed build, sponsored by the Windermere Police Department Foundation.
Two of the four start at Town Hall, one is at a downtown brewery, and the fourth is sponsored by a foundation tied to the town's own police department.
October 10: A Run That Pays for the Parks It Passes
The Run Among the Lakes started in the fall of 2001, after 9/11, as a way to bring the community together. The Windermere Parks & Recreation Committee hosts it, and the town says proceeds go directly to preserving and improving Windermere's public parks. So the course down the town's dirt roads, under old oaks and along the lakes, helps pay for the parks it runs past.
Most of this year's field is already set. Registration is capped at 1,200 runners and walkers. As of October 4, 2026, the RunSignup page showed the 5K sold out and six spots left in the 10K. The 10K is run-only, with a one hour and forty-five minute time limit. The 5K is open to runners and walkers. The Kids Run is free for children 7 and younger, and they don't need to register. Kids Run participants don't get an event T-shirt.
The morning schedule is tight:
- Event welcome at 7:00 a.m.
- 10K start at 7:10 a.m.
- 5K start at 7:35 a.m.
- Awards at 8:15 a.m.
- Kids Run at 8:45 a.m.
The town's parking graphic asks everyone to arrive by 6:40 a.m. and warns that roads will close once the race starts. It suggests four places to park:
- Family Church, 300 Main St.
- The Town Square lot, 119 W. 5th Ave.
- The Central Park dirt lot, 406 Oakdale St., between 4th and 5th
- The side lot at the Town Admin Building, 680 Main St., near Main and 7th Ave.
This year's course is new. The town posted the 2026 route as a map image. It hasn't published a written list of streets or closures. If you're driving out of downtown that Saturday morning and not running, check the map before you leave, or plan to be out before the 10K starts.
Packet pickup is Thursday, October 8, and Friday, October 9, from 3 to 6 p.m. at Town Hall. Race-day pickup is 6 to 7:10 a.m. Packets, medals and awards not picked up by race day can be collected the following week at the Windermere Administration Office, 614 Main Street. Dena O'Malley, chair of the Parks & Recreation Committee, is the contact for sponsorships.
The sponsor list leads into the next Saturday. Orlando Health is the title sponsor. Windermere Brewing is one of the Exclusive 25th Anniversary Signature Sponsors. The same brewery that helps fund the run on the 10th is hosting its own event a week later.
October 17: The Date Fifth Avenue Kept
The Windermere Craft Beer Fest has a longer history than most people realize. Its volunteers say it began in 2014 and grew into one of Central Florida's leading craft beer events. The Orange Observer reported that it came back in 2025 for the first time in six years. On September 22, 2026, the town announced that this year's festival was canceled and that ticket holders and sponsors would get full refunds.
The organizers' letter explains why. They had faced "challenges that have made it difficult to assemble the type of brewery participation necessary to deliver the festival at the level we believe it deserves." They also wrote that the beer industry, and how people experience beer and social events, has changed a lot since the festival began. The letter frames the cancellation as temporary:
This isn't goodbye. It's a pause while we figure out what's next. We hope to raise a glass with you again when the time is right.
A festival that depends on bringing in outside breweries had trouble bringing them in. A brewery that's already in town didn't have that problem. Windermere Brewing Co. said, "We were so sorry to hear this year's beer fest was canceled, so we decided to keep the beer flowing!" It scheduled its first Backup Beer Fest for the same Saturday, from noon to 4 p.m. at 111 W. Fifth Ave.
Tickets are $50 and include an official Backup Beer Fest T-shirt, a souvenir tasting cup, samples from every participating brewery, and 15% off draft beers. Three food trucks will be there: Lee's Famous Cheesesteaks, Tao Te Cheese and Bien Fuego. Tickets are on Ticketleap, linked from the Orange Observer's coverage.
One thing could confuse people. The town's online events calendar still listed "Windermere Beer Fest" on October 17, even after the cancellation notice ran on the town's live feed. Those are two separate events. The town-listed festival is canceled. The brewery's Backup Beer Fest is going ahead, and it's the one you need tickets for.
October 24: Public Works Drives the Hayride
The Halloween Costume Parade & Hayride runs on town staff. Parks & Recreation organizes it, Windermere Public Works provides the hayride, there are bounce houses, and the downtown businesses along Main Street hand out treats. It starts at 9:30 a.m. on Saturday, October 24, at Town Hall, 520 Main Street.
Local businesses have helped with this one before. When the town recapped the 2021 event, it thanked Main Street Mower for donating the trailers used for the hayride. This year's page names Public Works as the hayride provider.
The trick-or-treat stops are the shops along Main Street. Soon those may include Penelope's Coffee at 507 Main St. The Orange Observer reported on October 2 that renovations were nearly done and the shop was "expected to open this fall." Its owners, Leti Freitas and Joe Harris, live in Windermere. No opening date has been announced. Don't count on it being open by the 24th.
October 31, and a Monday Worth Knowing
The last Saturday of the month is a volunteer build. The annual Sleep in Heavenly Peace bunk-bed build, sponsored by the Windermere Police Department Foundation, is scheduled for October 31. The town is asking for volunteers and bedding donations. The post doesn't give a location or start time yet, so check the town's live feed before you go.
One weekday event fits in between. The Windermere Branch Library's StoryWalk and Fall Festival is Monday, October 12, from 10:30 a.m. to noon. It's for ages 6 to 12 and doesn't require registration. The branch is at 530 Main St.
Who runs each event matters for planning:
- Town-run events have firm details. The run and the hayride have posted start times, parking instructions and a pickup office for leftover packets and medals.
- Volunteer- and business-run events may still be filling in details. The bunk-bed build has no listed venue yet. The beer fest was canceled and replaced by a brewery event at a different address.
The town's live feed is the most up-to-date place to check, and in September it posted the cancellation before the events calendar was updated.
A lot of October in Windermere happens downtown: the run's start and finish, the brewery on Fifth Avenue, the hayride, and the shops handing out candy. If you live near downtown and want to know how your home compares in today's market, Abe Mendez offers a free home valuation and can walk you through the numbers in English or Spanish.
