Windermere Events This Weekend (Updated Weekly)

Tree lined entrance to Windermere Town Hall in Windermere, Florida — The tree lined entrance to Windermere Town Hall. Photo: Shutterstock, licensed.

Windermere is a small town tucked among the Butler Chain of Lakes, best known for oak lined Main Street and a Friday farmers market locals plan their week around. Here is what is on this weekend, updated every week.

October 16 to 18 · 0 verified in Windermere · 0 nearby

This weekendFull calendar ★ Things to do

No listed events for this view yet. See the full Windermere calendar.

Quiet stretchWindermere has a lighter events calendar this weekend. The usual local calendars were checked this week; not much is listed in town. Start with the picks below, or browse the full things to do list.

One easy plan

MorningWindermere Town Square Walkable village green for markets and meetups
MiddayButler Chain of Lakes shoreline parks Clear-water chain famous for boating and views
AfternoonDowntown Windermere Main Street Compact historic commercial street and shops

Still want a plan? Things to do in Windermere

A taste of the evergreen picks. The full ranked list adds itineraries, local tips, and the best free options.

★Windermere Town SquareMain St at Town HallDawn to duskFreeWalkable village green for markets and meetupsvia City calendarSee details →★Butler Chain of Lakes shoreline parksPublic lake access points around WindermereDawn to duskFreeClear-water chain famous for boating and viewsvia City calendarSee details →★Downtown Windermere Main StreetMain St corridorOpen dailyFree entryCompact historic commercial street and shopsvia City calendarSee details →★See the full Windermere listTop picks ranked by source consensus and editor review, with itineraries and tips for every kind of day.All things to do in Windermere →

Every weekend in Windermere

Recurring picks that run every Friday, Saturday, or Sunday, including this one.

EVERYWEEKWindermere Farmers MarketTown Square Park, Main St WindermereEvery FridayFri 9:00 am to 1:30 pmFreeWeekly Friday market in the town squarevia EventbriteSee event details →

Nearby this weekend

Distances are straight line miles from downtown Windermere. Each town has its own calendar.

Winter Gardenabout 6 miles awaySee all Winter Garden events →

EVERYWEEKWinter Garden Farmers MarketDowntown PavilionEvery SaturdaySaturday from 8:00 a.m. to 1:00 p.m. Downtown parking is free.Free entryFamily friendlyOutdoorWeather dependentThe highest-utility Saturday anchor, especially if you arrive early and build a walkable downtown loop from itvia City of Winter Garden Farmers MarketSee event details →

Orlandoabout 10 miles away, worth the driveSee all Orlando events →

EVERYWEEKOrlando Farmers Market at Lake EolaLake Eola Park, Eola Dr and Central BlvdEvery SundaySun 10:00 am to 3:00 pmFreeEvery Sunday downtown market since 1987via City calendarSee event details →

Celebrationabout 12 miles away, worth the driveSee all Celebration events →

EVERYWEEKCelebration Farmers MarketMarket Street, Celebration Town CenterEvery SundaySun 10:00 am to 2:00 pmFreeEvery Sunday market in the Town Centervia Venue siteSee event details →

Winter Parkabout 14 miles away, worth the driveSee all Winter Park events →

EVERYWEEKSaturday Farmers MarketCentral Park West Meadow, New York Ave and Morse BlvdEvery SaturdaySat 8:00 am to 1:00 pmFreeYear-round Saturday market returned to West Meadowvia City calendarSee event details →

NearbyWinter Garden 6 miOrlando 10 miCelebration 12 miWinter Park 14 miClermont 15 mi

Need a different day? See the full Windermere calendar · Next weekend

Know about a Windermere event we should list? Submit an event. See something wrong? Send a correction. Submissions are verified against official sources before listing; inclusion is editorial and not guaranteed.

Make it a parks weekend

Pair downtown with the parks

Most of Central Florida sits an easy drive from the theme parks, so a downtown morning pairs naturally with a lighter park evening. Check hours before you commit:

Next step

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Magic Kingdom hours All six WDW parks More destinations

About this Windermere events calendar

This list is hand curated for Windermere, Florida. Every listing is checked against local calendars, venue pages, and community listings, each card names its source, and past dates drop off automatically when the week turns over.

The picks under Every week are the dependable spine of the town. Start there, then layer on the dated specials as the season brings them. The list refreshes every Thursday.

Staying over? Compare hotels for this trip at Expedia.

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Frequently asked questions

How often is this page updated?

The event list refreshes weekly, dated items expire automatically, and the recurring picks run essentially every week of the year.

Are the listed events free?

Many are. Every card shows a cost pill when the venue lists one, and the Free filter narrows the list to free picks only.