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By Troy Herring |
March 3, 2021

Bo's Boys BBQ continues a family tradition

Brothers Jimmie and Jeremy Smith keep their father’s legacy of barbecue alive and well in Winter Garden.

West Orange Times & Observer
News

By Danielle Hendrix |
July 29, 2020

Meet Orange County School Board District 4 Candidate Dayna Gaut

Read our exclusive Q&A with Orange County School Board District 4 candidate Dayna Gaut.

West Orange Times & Observer
News

By Danielle Hendrix |
August 19, 2020

Horizon West to welcome new retailers, restaurants

Soon, residents in Hamlin, Summerport Village and Lakeside Village will have a larger selection of shops and other businesses to visit.

Southwest Orange
News

By Troy Herring |
August 26, 2020

Private schools create new athletic leagues

While Orange County Public Schools has suspended sports, private schools such as The First Academy, Foundation Academy and Windermere Prep will play as part of new leagues this fall.

Sports

By Troy Herring |
October 21, 2020

A legacy of Work: Natalie Work's volleyball career comes to an end

After six record-breaking years, Natalie Work’s time on the court for the Windermere Prep Volleyball team is over, and the senior is preparing for the future.

Sports

By Gabby Baquero |
December 12, 2018

Windermere Mayor Gary Bruhn to retire after 15 years of public service

Longtime Windermere Mayor Gary Bruhn led the town through some of its darkest days. Now, after 15 years, he is resigning from the post.

West Orange Times & Observer
News

By Tim Freed |
January 4, 2019

Trinity Prep eyes playoffs after postseason ban appeal

Trinity Preparatory School is once again eligible for football playoffs – and hopes to chase school history.

Winter Park - Maitland Observer
News

By Danielle Hendrix |
February 20, 2019

Windermere Prep senior receives appointment to West Point

Windermere Prep senior Grace Bennett is the first Laker in school history to be appointed to the U.S. Military Academy at West Point.

Southwest Orange
News

By Amy Quesinberry Price |
November 29, 2017

Powers Drive Baptist merges with Beulah Baptist Church

The two churches were experiencing dwindling congregation numbers but are now thriving as one.

West Orange Times & Observer
Neighborhood

By Observer Staff |
September 12, 2017

PHOTOS: Hurricane Irma rips through West Orange

A late turn in its path pushed the eye of Hurricane Irma closer to West Orange County.

West Orange Times & Observer
News

By Gabby Baquero |
October 4, 2017

Father-son duo trek 2,189-mile Appalachian trail

A father and son from Ocoee recently spent 177 days hiking the Appalachian Trail — the world’s longest continuously marked footpath that extends from Georgia to Maine.

West Orange Times & Observer
News

By Annabelle Sikes |
January 28, 2025

Orlando College of Osteopathic Medicine launches podcast

OCOM’s new podcast dives into the latest trends, challenges and insights in osteopathic medicine.

Observer School Zone

By Sam Albuquerque |
June 11, 2025

Athlete of the Week: Jozef Miesak, Windermere High

To close his Windermere High track career, Jozef Miesak added a state title to his 13 other first-place finishes in 2025 before hitting the track for the Yale Bulldogs.

Sports
Athlete of the Week

By Annabelle Sikes |
June 24, 2023

Town of Windermere closes in on permanent traffic solution

The Windermere Town Council moved forward with the first reading of an ordinance to implement a traffic-calming program on Oakdale Street by installing a diversion barrier.

Southwest Orange
News

By Sarah Wilson |
June 26, 2012

Anniversary of helicopter crash in Winter Park

Do you remember where you were when the helicopter crashed 15 years ago in Winter Park? Relive the accident with two men who will never forget.

Winter Park - Maitland Observer
Neighborhood

By Observer Staff |
November 2, 2011

Community Bulletin and Business Briefs

Winter Park resident Bonnie Jackson’s USTA Team, the “No Drama Mommas,” came in second in the nation.

Winter Park - Maitland Observer
News

By Annabelle Sikes |
January 28, 2023

Listening session: Windermere residents sound off on pavilion

A project between Windermere Rotary Inc. and the West Orange Healthcare District may bring an outdoor pavilion to the northwest corner of Town Square Park.

Southwest Orange

By Annabelle Sikes |
June 17, 2022

Orange County mayor delivers 2022 State of the County

Jerry L. Demings highlighted the accomplishments and discussed the future of the county on Friday, June 10, at the Orange County Convention Center.

West Orange Times & Observer
News

By Amy Quesinberry Price |
August 31, 2016

Herman R. Gebert Jr. : Career military man served during three wars

Hebert served during World War II and the Korean and Vietnam wars.

Southwest Orange
Neighborhood

By Jennifer Nesslar |
February 25, 2016

Club seeks to make backyard chickens legal in Winter Garden

The Winter Garden Chicken Club wants to make backyard chickens legal in Winter Garden and hopes to dispel foul perceptions of the egg-producing birds.

West Orange Times & Observer
News

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