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By Danielle Hendrix |
March 17, 2019

PHOTOS: 2019 Windermere St. Patrick's Day Celebration

The town of Windermere celebrated St. Patrick’s Day with family-friendly festivities while raising money for its police foundation.

Southwest Orange
Neighborhood

By Troy Herring |
April 16, 2018

PHOTOS: Earth Day in the Park

Locals and visitors alike enjoyed a day of festivities as they learned about how to better take care of their environment.

Winter Park - Maitland Observer
News

By Liz Ramos |
April 17, 2025

Bloom & Grow Garden Society to celebrate Earth Day in Winter Garden

For Earth Day, Bloom & Grow will kick off its "100 Trees for 100 Years" project.

West Orange Times & Observer
News

By Amy Quesinberry Price |
January 26, 2025

PHOTOS: Town celebrates Oakland Heritage Day

Attendees enjoyed the cool weather while learning about Oakland's history and enjoying a day of music and vendors.

West Orange Times & Observer
News

By Michael Eng |
April 1, 2021

OBSERVED: Do you really want to #StopAsianHate?

For the first time in my life, people are paying attention to the plight of Asian Americans. I believe that’s a good thing. But the conversation needs to be redirected. 

West Orange Times & Observer
Opinion

By Andrea Mujica |
April 28, 2023

PHOTOS: Windermere High baseball ready for districts play

The Wolverines defeated the Bulldogs 9-0 during their last game of the 2022-23 regular season Thursday, April 27.

Sports
Game Film

By Amy Quesinberry Price |
August 11, 2016

TBT: Winter Garden, Ocoee compete in Dog and Cat Bowl

The annual competition was named for the teams facing each other in Ocoee and Winter Garden, the Bulldogs and the Wildcats.

West Orange Times & Observer
Neighborhood

By Andrea Mujica |
August 27, 2022

PHOTOS: Ocoee falls 13-12 to Apopka

Even though both teams displayed strong defense skills, the Knights fell to the Blue Darters during their first game of the season.

West Orange Times & Observer
News

By Steven Ryzewski |
February 25, 2015

No. 4 Olympia girls lacrosse tops Winter Park to stay undefeated

West Orange Times & Observer
News

By Steven Ryzewski |
March 19, 2015

Southwest Middle wins OCPS hoops title

West Orange Times & Observer
News

By Isaac Babcock |
March 6, 2013

Knights hit the road before C-USA tournament

Keith Clanton tried to give fans something to remember in the men’s basketball team’s last night on their home court this season.

Winter Park - Maitland Observer
Sports

By Troy Herring |
September 3, 2020

PHOTOS: Students, parents rally for groups left out of upcoming football season

The rally was in response to OCPS' recent announcement that it was partly limiting attendance at football games by not allowing cheer, dance, band and JROTC to participate on Friday nights.

West Orange Times & Observer
News

By Chris Martucci |
October 15, 2021

Week 8 Football Schedule

Olympia-Windermere and Lake Buena Vista–Horizon are the only two home games on the schedule.

West Orange Times & Observer
News

By Sam Albuquerque |
July 5, 2024

Windermere High has announced Nicole Vinas as its next girls indoor volleyball coach

Vinas will take over a Wolverines team that finished 16-7 last season and should return its top hitter and setter.

Sports
High Schools

By Sam Albuquerque |
March 8, 2025

Horizon football's Evan Reinhart commits to Stetson

The Hawks' 6-foot-6, 320-pound versatile offensive lineman will be playing his college ball down the road in the DeLand next season.

Sports
High Schools

By Andrea Mujica |
September 21, 2023

PHOTOS: West Orange High swim defeats Olympia

The Warriors’ swim teams brought home wins on both, the boys and girls side, after competing at a dual meet against the Titans Wednesday, Sept. 20.

Sports
Game Film

By Sam Albuquerque |
October 17, 2024

Windermere High boys golf ties for second at Birdies for the Brain Invitational

The Wolverines shot 295 in Winter Park High’s tournament and fundraiser at Rio Pinar Golf Club. The First Academy finished fourth with a score of 297.

Sports
High Schools

By Megan Bruinsma |
February 18, 2026

Dr. Phillips’ Caleb Walls takes the helm of football team

At 27 years old Caleb Walls begins his first head coach position.

Sports
High Schools

By Megan Bruinsma |
April 17, 2026

Dr. Phillips High baseball team celebrates seven Class of 2026 commitments

The Panthers will graduate seven seniors who will go on to the next level.

Sports
High Schools

By Observer Staff |
May 18, 2016

Calendar

The fifth annual Maitland Public Library 5K will be held on Saturday, May 21 at 7:30 a.m.

Winter Park - Maitland Observer
Neighborhood

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