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By Leticia Silva |
October 31, 2025

Healthy West Orange to host annual Health & Harvest Festival

The event will take place from 8 a.m. to 1 p.m. Saturday, Nov. 8, at Winter Garden’s farmers market.

West Orange Times & Observer
Neighborhood

By Megan Bruinsma |
February 11, 2026

Ocoee girls basketball team wins 2026 District Championship

For the fourth consecutive season, the Knights won the district championship.

Sports
High Schools

By Leticia Silva |
March 9, 2026

New support group at AdventHealth Winter Garden

The "Baby Bunch" breastfeeding support group is designated for postpartum moms to connect on a weekly basis.

West Orange Times & Observer
News

By Megan Bruinsma |
March 20, 2026

Foundation Academy’s Charlie Capozzoli committs to Eckerd

The senior baseball player will take his talents to Eckerd College.

Sports
High Schools

By Michael Eng |
April 2, 2026

Crossline Community Church rolls with annual Easter Egg Hunt

The event will take place from 1 to 3 p.m. Saturday, April 4, at Crossline Park, 17922 Old YMCA Road, Winter Garden.

Arts + Entertainment
Things to Do

By Annabelle Sikes |
January 14, 2022

Dr. Phillips High community remembers Bill Spoone

Spoone was the first principal at Dr. Phillips High School and an influential member of the community.

West Orange Times & Observer
News

By Annabelle Sikes |
January 7, 2022

FORECAST: AdventHealth makes progress in the Winter Garden community

Notable recent developments at AdventHealth Winter Garden include the upcoming opening of the inpatient tower, new services being offered and new leadership.

West Orange Times & Observer
News

By Anita Lohman |
July 3, 2012

Women and retirement savings

Women have made great strides as professionally, yet one unfortunate fact remains: women are lagging behind men on retirement planning and saving.

Winter Park - Maitland Observer
Opinion

By Amy Quesinberry Price |
June 30, 2022

This week in West Orange County history: June 30, 2022

These are the people and events that shaped the West Orange County of today.

West Orange Times & Observer
News

By Isaac Babcock |
February 18, 2016

UCF Knights in trouble, Winter Park Wildcats claw way into regional final

It was a rough night in Texas as the Knights met Houston for the first time and fell 82-58 on a slew of late-game turnovers.

Winter Park - Maitland Observer
Sports

By Randy Knight |
September 8, 2016

Winter Park City Talk

CoffeeTalk featuring Commissioner Cooper will be held Thursday, Sept. 15, at 8 a.m., at the Winter Park Welcome Center located at 151 W. Lyman Ave.

Winter Park - Maitland Observer
News

By Isaac Babcock |
July 21, 2016

Despite blowouts, Winter Park Diamond Dawgs still have a shot

The Winter Park Diamond Dawgs fell deeper into a hole last weekend, though not far enough to drop below the Leesburg Lightning in the Florida Collegiate Summer League standings.

Winter Park - Maitland Observer
Sports

By Isaac Babcock |
May 4, 2016

Wildcats, Eagles knocked out of postseason

Winter Park High School and Edgewater High School baseball teams both saw their seasons come to an end last Wednesday.

Winter Park - Maitland Observer
Sports

By Josh Garrick |
May 1, 2013

Josh Garrick: Culture Worthy of Your Calendar

May is one of the best months for travelers to get more out of their time here.

Winter Park - Maitland Observer
Neighborhood

By Observer Staff |
December 4, 2013

Family Calendar

On Thursday, Dec. 5, the Charles Hosmer Morse Museum of American Art presents its free annual Christmas in the Park event for the 35th year in downtown Winter Park.

Winter Park - Maitland Observer
Neighborhood

By Annabelle Sikes |
May 1, 2023

Students speak out against Innovation Montessori High School

The school has announced it will be cutting back the high school to merge it with middle school.

Observer School Zone
News

By Sarah Wilson |
October 26, 2011

Rollins student sets up bakery in South Africa

Rollins College student combines her education, passion to help women in South Africa.

Winter Park - Maitland Observer
Neighborhood

By Gabby Baquero |
February 1, 2017

Coil conundrum: Faulty Lennox AC units anger homeowners

A manufacturing design with Lennox-brand AC units has caused new homeowners much grief as they fork over hundreds of dollars for unexpected repair expenses.

West Orange Times & Observer
News

By Amy Quesinberry Price |
April 23, 2015

'Dolly' to say hello on West Orange High School stage

Arts + Entertainment
Arts + Culture

By Danielle Hendrix |
January 12, 2018

BLACK TIE: Windermere Wine & Dine celebrates 5 years with new grant

Now in its fifth year, the Windermere Wine & Dine continues to see more success than ever — thanks to organizers and the town’s embrace.

Black Tie

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