Your Town | Orange Observer

Orange Observer | Your Town

Michael Eng
September 10, 2025

Windermere to host 9/11 sunset service

The town will honor the families and first responders whose lives were forever changed that day.

Arts + Entertainment
Things to Do

Michael Eng
September 3, 2025

Celebrate 120 years of the West Orange Times & Observer

The anniversary bash takes place from 5:30 to 7 p.m. Thursday, Sept. 11, at our office, 661 Garden Commerce Parkway, Suite 180, Winter Garden.

West Orange Times & Observer
News

Michael Eng
September 2, 2025

West Orange Junior Service League member spearheads hygiene kit drive for local middle schools

The West Orange Junior Service League is proud to celebrate the compassion and leadership of one of its own.

Observer School Zone

Michael Eng
August 26, 2025

Win tickets to Chris Brown, Andrea Bocelli

You can score tickets to two of the hottest upcoming shows and support the Winter Garden Art Association and SOBO Art Gallery at the same time.

Arts + Entertainment
Things to Do

Michael Eng
August 26, 2025

SAVE THE DATE: Windermere High Fall Bash set for Sept. 17

Attendees will enjoy drinks, food, music and a silent auction — all to raise funds for faculty and club grants for the school.

Arts + Entertainment
Things to Do

Michael Eng
August 5, 2025

Observer wins awards for journalism, advertising

The West Orange Times & Observer and Southwest Orange Observer won awards for its journalism, design and advertising at the 2025 Florida Media Conference.

West Orange Times & Observer
Your Town

Sam Albuquerque
July 24, 2025

Match play magic: Fundraiser pits golfers against NBA legends

Headlined by Hall-of-Fame basketball player Vince Carter, Windermere Elementary’s first fundraising tournament offers golfers the chance to play 18 holes against former Orlando Magic players.

Arts + Entertainment
Things to Do

Leticia Silva
June 21, 2025

PHOTOS: Juneteenth celebration in Winter Garden

The city of Winter Garden celebrated Juneteenth on Saturday, June 21.

West Orange Times & Observer

Sam Albuquerque
June 19, 2025

Winter Garden Squeeze announces free tickets for kids for remainder of 2025

In partnership with local preschool The Learning Experience, all kids 12 and under get in free to the Squeeze’s remaining home games.

Sports

By None
June 11, 2025

Winter Garden to celebrate Juneteenth at Charlie Mae Wilder Park

The annual event honors legacy and community with music, speakers and family activities.

Arts + Entertainment
Things to Do

Sam Albuquerque
May 30, 2025

Florida League of Cities recognizes Ocoee Youth Council

As part of the Florida League of Cities’ Youth Council Excellence Project contest, the Ocoee chapter’s project to clean and beautify the Ocoee Cemetery was selected as one of three winners.