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By Danielle Hendrix |
February 26, 2020

Taking root: Bloom & Grow partners with community to plant 1,000 trees

Winter Garden’s Bloom & Grow Garden Society and Cherrylake Tree Farm recently partnered with other organizations to plant 1,000 bald cypress trees at Tucker Ranch.

West Orange Times & Observer
News

By Amy Quesinberry Price |
March 4, 2020

1954-2020: Former Winter Garden fire chief Randy Dollar dies

Randy Dollar, Winter Garden fire chief from 1994 to 2002, led the city’s department during an era of growth and change.

West Orange Times & Observer
Neighborhood

By Amy Quesinberry Price |
May 16, 2018

Calendar for the Week of 5-17-18

Find out what events are taking place this week and weekend in West Orange County.

West Orange Times & Observer
Neighborhood

By Amy Quesinberry Price |
June 27, 2018

Calendar for the Week of June 28, 2018

Find out what activities are taking place in West Orange County this week and weekend.

West Orange Times & Observer
Neighborhood

By Brittany Gaines |
June 8, 2017

Summer of Love: Reflection on Pulse

In the last year, West Orange artists have created a variety of pieces in memory of the 49 people who died in the Pulse nightclub shooting

Arts + Entertainment
Arts + Culture

By Amy Quesinberry Price |
February 12, 2019

Bill Criswell, Home At Last founder, dies at age 93

Bill Criswell, longtime Windermere resident, World War II veteran and Home At Last founder, dies at age 93.

Southwest Orange
News

By Troy Herring |
August 23, 2018

Orangewood Christian Rams ready for season | Observer Preps

Despite the graduation of quarterback and leader Ian Stone, the Rams are poised for another strong season.

Winter Park - Maitland Observer
Sports

By Sam Albuquerque |
April 16, 2025

Meet the husband-and-wife duo bringing a $1 billion youth sports complex to Ocoee

Jaime and Anne-Marie Douglas are the CEO and President of the Montierre Development team behind The Dynasty|Ocoee project set to revolutionize the youth sports landscape as we know it.

West Orange Times & Observer
News

By Sam Albuquerque |
June 3, 2025

Meet the 2025 All-Orange Observer baseball teams and Player of the Year

To celebrate West, Southwest Orange County's phenomenal season on the baseball diamond, here are the best the area had to offer in 2025.

Sports
High Schools

By Liz Ramos |
September 4, 2025

Celebrate Tsaber's birthday at Bill Frederick Park at Turkey Lake

Tsaber, an Arabian horse, is turning 38 years old this month.

Arts + Entertainment
Things to Do

By Annabelle Sikes |
July 22, 2023

Winter Garden commission begins 2023-24 budget talks

The commission approved unanimously setting the proposed millage rate at the current rate of 4.5 mills at the Thursday, July 13, meeting.

West Orange Times & Observer
News

By Louis Roney |
December 1, 2010

Play On!

Obama’s thoughts and words

Winter Park - Maitland Observer
Opinion

By Kristy Vickery |
December 23, 2010

Leave it to the experts

Orange County Public Schools pilot a new program that has chefs serving up healthier cafeteria food

Winter Park - Maitland Observer
News

By Josh Garrick |
April 1, 2010

Culture worthy of your calendar

Winter Park’s dynamic duo of painting and sculpture – John and Lynn Whipple – are married, talented, and fun!

Winter Park - Maitland Observer
Neighborhood

By Kristy Vickery |
May 27, 2010

Coaching students for college

A local assistance program takes the stress out of finding and enrolling for higher education

Winter Park - Maitland Observer
News

By Observer Staff |
July 14, 2010

Our Observation

In February an American bulldog mauled a 3-year-old Ocala girl to death after she wandered into its pen.

Winter Park - Maitland Observer
Opinion

By Observer Staff |
March 28, 2012

Community Bulletin

Joseph Reece White of Winter Park High School won third place at the Shakespeare Competition.

Winter Park - Maitland Observer
News

By Observer Staff |
May 16, 2012

Community Bulletin

The Holocaust Center in Maitland held its annual Dinner of Tribute at the Rosen Plaza on April 26.

Winter Park - Maitland Observer
News

By Josh Garrick |
March 11, 2010

Culture worthy of your calendar

Free outdoor concert by the Orlando Philharmonic, All of Shakespeare — shortened — really shortened!, Richard Marx at the Plaza Theater

Winter Park - Maitland Observer
Neighborhood

By Isaac Babcock |
March 8, 2011

Sprinkel, Leary prevail

Winter Park has two new city commissioners, Steven Leary and Sarah Sprinkel.

Winter Park - Maitland Observer
News

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