Mark your calendars, because Light Up Windermere is returning on November 20th!
Join us for an evening of food, live performances, and holiday festivities that will get you into the spirit of the season.
Stay tuned for more details as we get closer to the event!
Join us for an evening of food, live performances, and holiday festivities that will get you into the spirit of the season.
Stay tuned for more details as we get closer to the event!
RUN AMONG THE LAKES ROAD CLOSURE:
Portions of Main Street will be closed Saturday, October 10th for the annual Run Among the Lakes. Main Street from 6th Avenue to Park Avenue will be shut down from approximately 7:25 a.m. until 8 a.m. for the race.
We appreciate your patience.
Portions of Main Street will be closed Saturday, October 10th for the annual Run Among the Lakes. Main Street from 6th Avenue to Park Avenue will be shut down from approximately 7:25 a.m. until 8 a.m. for the race.
We appreciate your patience.
🚨 IMPORTANT RUN AMONG THE LAKES UPDATES 🚨
The Run Among the Lakes 5K WILL take place tomorrow, Saturday, October 10th. However, there will not be a 10K run. All runners will start the 5K race at 7:35 a.m.
While the 10K race has been canceled, 10K runners are invited to join our 5K race. You'll keep your 10K bib, receive your 10K finisher medal, and compete in your own separate award division, including awards for top overall finishers.
VIRTUAL OPTION: Registered 10K runners who prefer not to participate in the 5K may choose a virtual option when the roads are clearer and still receive their race goodies!
Packet pickup will be available today at Town Hall from 3 - 6 p.m. Anyone signed up for the run is encouraged to check their email for additional information from race organizers, or visit https://runsignup.com/Race/FL/Windermere/Windermere5KRunAmongtheLakes to receive updates as they become available.
Weather, Weather, Weather! ☔
It's raining in Windermere, and after days of gray skies and seemingly endless rain, we know everyone is wondering the same thing: Will we be running on Saturday?
One of the things that makes our little town so special is its beautiful canopy of old oak trees and charming dirt roads. We love them! But as you can imagine, those same dirt roads present some challenges when Mother Nature decides to send us days and days of rain.
As of today, our race is still scheduled to take place on Saturday, October 10. However, we are actively assessing the conditions and exploring every option available.
IMPORTANT: An official decision regarding Saturday's race will be announced tomorrow, Friday, October 9, at 11:00 a.m.
Our biggest concern isn't simply whether it will be raining on race morning. It's whether our dirt roads will be safe and suitable for runners. Standing water, puddles, uneven surfaces, and saturated roads are all factors we must carefully consider. Unlike many races, a significant portion of our course is not paved.
Please know that our Public Works Department, Town Administration, Windermere Police Department, Sommer Sports, and Parks and Recreation Committee are all working together to evaluate the situation.
We want nothing more than to celebrate our 25th Anniversary Run Among the Lakes with all of you this Saturday! We've worked so hard to make this a special year, and we know so many of you are looking forward to being part of it.
A note about packet pickup:
Packet pickup is still available today as scheduled. However, if your schedule allows, we kindly encourage you to hold off until after tomorrow's announcement, when we will have a clearer picture of our plans.
We know this uncertainty isn't ideal, especially for those of you making travel arrangements or planning your weekend around the race. We truly appreciate your patience, flexibility, and understanding as we work through a situation that is largely out of our control.
Our priority is, and always will be, the safety of our runners, volunteers, and community.
Thank you for loving this little race as much as we do. We're keeping our fingers crossed, watching the skies, and doing everything we can to make our 25th anniversary celebration happen.
Stay tuned, stay dry, and thank you for your support!
Our annual Sleep in Heavenly Peace bunk bed build is fast approaching, and now you have another location to drop off your donations!
New, twin-sized bedding can be dropped off at Flippers Pizza Co. on Old Brick Road, or you can bring your donation to the Windermere PD lobby. The Windermere Police Department Foundation would like to thank Flippers for their partnership and support of this great cause!
As a reminder, the bunk bed build is coming up on Saturday, October 31st from 8 a.m. till noon at Town Square Park. If you would like to volunteer, click here to sign up: https://volunteer.shpbeds.org/opportunities/xBWeggpNcc
New, twin-sized bedding can be dropped off at Flippers Pizza Co. on Old Brick Road, or you can bring your donation to the Windermere PD lobby. The Windermere Police Department Foundation would like to thank Flippers for their partnership and support of this great cause!
As a reminder, the bunk bed build is coming up on Saturday, October 31st from 8 a.m. till noon at Town Square Park. If you would like to volunteer, click here to sign up: https://volunteer.shpbeds.org/opportunities/xBWeggpNcc
UPDATE: Due to the high volume of responses, we are no longer accepting applications for the role of Administrative Assistant.
The Town of Windermere is now hiring an Administrative Assistant!
The Administrative Assistant is responsible for greeting citizens, directing the general public to appropriate departments for assistance, and answering citizen's questions regarding facility rentals, special events, and more.
If you're interested in applying, email your resume to Theresa Syphers at tsyphers@windermere.gov.
To view a full job description, or to see other employment opportunities, click here: https://www.town.windermere.fl.us/page/employment-opportunities
FREE ASL classes are starting soon! Join us starting Friday, October 9th for FREE American Sign Language classes!
The Town of Windermere, in partnership with Council Member Mandy David, is offering ASL classes for adults and teens. The 8-week course builds week to week, so consistent attendance is encouraged.
Details:
📍 Community Conference Room
Town of Windermere Administrative and Police Complex
614 Main Street, Building 100
🗓 Fridays
• ASL 1 (Beginner): 1:00–2:00 p.m.
• ASL 2 (Intermediate): 2:00–3:00 p.m.
There is no need to register in advance for this class. Please note, there will be no classes held on Friday, November 27th in observance of the Thanksgiving holiday.
The Town of Windermere, in partnership with Council Member Mandy David, is offering ASL classes for adults and teens. The 8-week course builds week to week, so consistent attendance is encouraged.
Details:
📍 Community Conference Room
Town of Windermere Administrative and Police Complex
614 Main Street, Building 100
🗓 Fridays
• ASL 1 (Beginner): 1:00–2:00 p.m.
• ASL 2 (Intermediate): 2:00–3:00 p.m.
There is no need to register in advance for this class. Please note, there will be no classes held on Friday, November 27th in observance of the Thanksgiving holiday.
Please join us in wishing a very happy birthday to our very own Mayor Andy Williams! 🎉
Thank you, Mayor Williams, for your ongoing service to the Town of Windermere and your dedication to making our community a more vibrant place for residents and visitors.
Thank you, Mayor Williams, for your ongoing service to the Town of Windermere and your dedication to making our community a more vibrant place for residents and visitors.
Planning to carve some pumpkins this Halloween season? Why not join your neighbors for a fun community gathering at the same time! 🎃
The Windermere Historic Preservation Board is hosting their 2nd Annual Pumpkin Carving Potluck on Sunday October 25th, from 4 to 6 p.m. for Town residents and their guests.
Bring your own pumpkin, carving tools, and a dish to share as we celebrate fall together. The event is free, but residents are asked to reserve their spot.
RSVP here: https://www.eventbrite.com/e/2nd-annual-pumpkin-carving-potluck-tickets-2002803231379
The Windermere Historic Preservation Board is hosting their 2nd Annual Pumpkin Carving Potluck on Sunday October 25th, from 4 to 6 p.m. for Town residents and their guests.
Bring your own pumpkin, carving tools, and a dish to share as we celebrate fall together. The event is free, but residents are asked to reserve their spot.
RSVP here: https://www.eventbrite.com/e/2nd-annual-pumpkin-carving-potluck-tickets-2002803231379
Looking for some fun fall activities to do with your little ones?
The Windermere Branch Library is hosting a StoryWalk and Fall Festival on Monday, October 12th! Stop by from 10:30 a.m. till noon to enjoy some fall-themed fun.
Recommended for ages 6-12. No registration required.
The Windermere Branch Library is hosting a StoryWalk and Fall Festival on Monday, October 12th! Stop by from 10:30 a.m. till noon to enjoy some fall-themed fun.
Recommended for ages 6-12. No registration required.
DISCUSSION TONIGHT: In case you missed our first Amendment 3 discussion with Windermere Town Manager Robert Smith, you have another chance to be part of the conversation!
Join us TONIGHT, October 1st at 6 p.m. to learn more about Amendment 3 and what it could mean for the Town and the services we provide to our residents.
Attend via Zoom:
https://us06web.zoom.us/j/85413920537?pwd=DUsMNRsxgfSh8LsnedEOtk0yEcBlak.1
Meeting chat link
https://us06web.zoom.us/launch/jc/85413920537
Meeting ID: 854 1392 0537
Passcode: 294911
“Pool Water Disposal”
Never drain pool or spa water into storm drains—it’s harmful to aquatic life.
Always drain onto grass or follow proper disposal guidelines.
For more information, visit our Stormwater Page: https://www.town.windermere.fl.us/page/stormwater
#NPDES #CleanLakes #IllicitDischarge
MAIN STREET CLOSURE TODAY:
A section of Main Street, from 2nd to 7th Avenue, will be closed this afternoon between 4:30 and 5:30 p.m.
Expect detours and delays in the area during this time, and please drive with caution.
A section of Main Street, from 2nd to 7th Avenue, will be closed this afternoon between 4:30 and 5:30 p.m.
Expect detours and delays in the area during this time, and please drive with caution.
COMMUNITY DISCUSSION TONIGHT: Amendment 3 could have a lasting impact on our local communities. Do you know what it could mean for yours?
Join the West Orange Chamber of Commerce for a Community Conversation with West Orange Mayors & Managers to hear directly from the local leaders who serve our communities.
We’ll discuss Amendment 3 and what it could mean for local services, our communities, and quality of life — while giving you the opportunity to ask questions and become a more informed voter.
September 30, 2026
6:00 PM
Ocoee Lakeshore Center
REGISTER HERE: https://biz.wochamber.com/.../amendment-3-town-hall-3213
Participating Municipalities: Apopka • Oakland • Ocoee • Windermere • Winter Garden
Moderator: Mike Eng, Editor & Publisher, Observer Media Group
Have a question you’d like addressed? Submit it in advance to info@wochamber.com.
Join the West Orange Chamber of Commerce for a Community Conversation with West Orange Mayors & Managers to hear directly from the local leaders who serve our communities.
We’ll discuss Amendment 3 and what it could mean for local services, our communities, and quality of life — while giving you the opportunity to ask questions and become a more informed voter.
September 30, 2026
6:00 PM
Ocoee Lakeshore Center
REGISTER HERE: https://biz.wochamber.com/.../amendment-3-town-hall-3213
Participating Municipalities: Apopka • Oakland • Ocoee • Windermere • Winter Garden
Moderator: Mike Eng, Editor & Publisher, Observer Media Group
Have a question you’d like addressed? Submit it in advance to info@wochamber.com.
Looking for a chance to give back in our community? Join us for the annual Sleep in Heavenly Peace bunk bed build on October 31st! 😴
Click here to sign up as a volunteer: https://volunteer.shpbeds.org/opportunities/xBWeggpNcc
This event, sponsored by the Windermere Police Department Foundation, helps provide safe, comfortable beds for children in our area.
Not able to volunteer? You can drop off new, twin-sized bedding at the Windermere Police lobby, or click the link to donate online: https://shpbeds.org/?form=FUNUMTJEYWB&CId=0014x000016wQq8
Click here to sign up as a volunteer: https://volunteer.shpbeds.org/opportunities/xBWeggpNcc
This event, sponsored by the Windermere Police Department Foundation, helps provide safe, comfortable beds for children in our area.
Not able to volunteer? You can drop off new, twin-sized bedding at the Windermere Police lobby, or click the link to donate online: https://shpbeds.org/?form=FUNUMTJEYWB&CId=0014x000016wQq8
Attention, drivers! ⚠
The Town of Windermere Public Works team will be out starting at 7 a.m. tomorrow, Tuesday, September 29th, performing landscaping work at the 5th and 6th Avenue roundabouts. The work is expected to last the remainder of the week.
Please allow extra travel time, and be cautious when driving through the area.
ATTENTION: MAIN STREET CLOSURE
A section of Main Street, from 2nd to 7th Avenue, will be closed on Wednesday, September 30th between 4:30 and 5:30 p.m.
Expect detours and delays in the area during this time, and please drive with caution.
A section of Main Street, from 2nd to 7th Avenue, will be closed on Wednesday, September 30th between 4:30 and 5:30 p.m.
Expect detours and delays in the area during this time, and please drive with caution.
Amendment 3 could have a lasting impact on our local communities. Do you know what it could mean for yours?
Join the West Orange Chamber of Commerce for a Community Conversation with West Orange Mayors & Managers to hear directly from the local leaders who serve our communities.
We’ll discuss Amendment 3 and what it could mean for local services, our communities, and quality of life — while giving you the opportunity to ask questions and become a more informed voter.
September 30, 2026
6:00 PM
Ocoee Lakeshore Center
REGISTER HERE: https://biz.wochamber.com/.../amendment-3-town-hall-3213
Participating Municipalities: Apopka • Oakland • Ocoee • Windermere • Winter Garden
Moderator: Mike Eng, Editor & Publisher, Observer Media Group
Have a question you’d like addressed? Submit it in advance to info@wochamber.com.
Attention, drivers! ⚠
The Town of Windermere Public Works team will be out tomorrow, Monday, September 28th, from 7:00 a.m. to 4:00 p.m. performing landscaping work at the Park Avenue roundabout.
Please allow extra travel time, and be cautious when driving through the area.
The Town of Windermere Public Works team will be out tomorrow, Monday, September 28th, from 7:00 a.m. to 4:00 p.m. performing landscaping work at the Park Avenue roundabout.
Please allow extra travel time, and be cautious when driving through the area.
ATTENTION: We are experiencing technical issues with gates that require a code to access Town of Windermere parks and amenities.
Residents may not have access using their codes through the weekend, but we are working to resolve the issue.
The Town of Windermere apologizes for the inconvenience, and we thank you for your patience.
Residents may not have access using their codes through the weekend, but we are working to resolve the issue.
The Town of Windermere apologizes for the inconvenience, and we thank you for your patience.
