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By Troy Herring |
November 1, 2020

PHOTOS: Windermere Halloween Parade

Children in Windermere filled their Halloween bags with candy early on Saturday, as the town held its Halloween Parade.

Southwest Orange
News

By Danielle Hendrix |
May 6, 2019

BLACK TIE: West Orange Junior Service League’s Run for the Roses 2019

Outlandish hats, colorful outfits and some casino-style games marked a celebration in Windermere of the 145th Kentucky Derby.

Southwest Orange
Neighborhood

By Harry Sayer |
December 3, 2017

Black Tie: Orlando REP's Holiday Family Gala

The Orlando theatre hosted its fifth annual gala with some help from Mr. and Ms. Claus.

Winter Park - Maitland Observer
News

By Harry Sayer |
February 7, 2018

BLACK TIE: Weekend of the Arts VIP Reception

Winter Park’s arts scene gathered at Cornell Fine Arts museum for the official announcement of the upcoming arts weekend.

Winter Park - Maitland Observer
News

By Danielle Hendrix |
September 24, 2018

PHOTOS: Kugel Kook-Off at Rosen JCC

Cook-off attendees sampled nearly a dozen varieties of kugel, both sweet and savory, and voted for their favorites.

Southwest Orange
Neighborhood

By Danielle Hendrix |
October 30, 2018

PHOTOS: Whispering Oak Elementary Trunk-or-Treat

Students showed off their cool costumes as they roamed around and gathered treats from parents and volunteers.

West Orange Times & Observer
Neighborhood

By Sam Albuquerque |
August 4, 2024

West Orange High alum, swimmer Victor Wright wins 50-meter breaststroke at Special Olympics Florida event

Wright won the Special Olympics Florida Area 6 swimming competition and will move on to regionals.

Sports

By Amy Quesinberry Price |
March 10, 2024

PHOTOS: Windermere Fine Art Show

Gorgeous weekend weather enticed residents outside to mingle among the artists in downtown Windermere.

West Orange Times & Observer
News

By Sam Albuquerque |
July 2, 2025

Winter Garden to host annual Party in the Park

The event is from 6 to 10 p.m. at Newton Park on Lake Apopka, 31 W. Garden Ave.

Arts + Entertainment
Things to Do

By Amy Quesinberry Price |
October 30, 2024

Rotary foundation hosting 'A Taste of Dr. Phillips'

The club's foundation is holding its annual event that features delectable bites and cocktails from the area's top restaurants.

West Orange Times & Observer
News

By Leticia Silva |
December 11, 2025

Oakland to host free golf cart parade

The parade will start at 5 p.m. Saturday, Dec. 13, at Speer Park.

West Orange Times & Observer
News

By Megan Bruinsma |
March 11, 2026

Windermere Prep boys track and field athlete breaks school record

The junior Akai Tonge broke the school record in the 400-meter hurdles.

Sports
High Schools

By Sam Albuquerque |
January 11, 2024

Meet the Forecast 14: The group of players, coaches and sports people that'll define West, Southwest Orange County sports

Whether it be on the field, court, sidelines or classroom, these 14 individuals are going to make impacts felt this year.

Sports
High Schools

By Clyde Moore |
May 21, 2012

Peacocks

What's more popular in Winter Park than peacocks? Today's open season and I go hunting for them on North Park Ave!

Winter Park - Maitland Observer
Opinion

By Troy Herring |
April 29, 2020

Observer All-Area teams: Boys lacrosse

The top boys lacrosse players from around the area make up our All-Area teams.

Sports

By Zena Sulkes, president of the Jewish Pavilion |
March 2, 2011

Supporting your loved ones as they age

How do I know when it is time for my loved one to need additional care?

Winter Park - Maitland Observer
Neighborhood

By Steven Ryzewski |
January 12, 2016

Lions land record All-State recognition

Foundation Academy had two first team honorees and two honorable mentions in Class 2A — a program best.

Sports

By Tim Freed |
January 21, 2016

Winter Park board considers vacating Palmetto Avenue

Winter Park might cut a road down to size if it means making a city property easier to sell.

Winter Park - Maitland Observer
News

By Steven Ryzewski |
December 8, 2016

Youth football: Pair of Bobcats teams prep for nationals

The West Orange 14U and 8U teams will compete against some of the best teams around the country next weekend in Davenport.

Sports
Youth Sports

By Steven Ryzewski |
July 10, 2014

Synchronized in Seattle: Local team returns from national competition

Sports

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