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By Leticia Silva |
February 25, 2026

Windermere Fine Art Show to take place this weekend

The 11th annual event will take place from 11 a.m. to 5 p.m. Saturday, Feb. 28, and 10 a.m. to 5 p.m. Sunday, March 1.

Arts + Entertainment
Things to Do

By Annabelle Sikes |
February 18, 2022

Windermere Lakes Cleanup Day happening this weekend

The cleanup will begin at Fernwood Park at 1:30 p.m. on Sunday, Feb. 20.

West Orange Times & Observer
News

By Steven Ryzewski |
December 7, 2016

PHOTOS: West Orange, Apopka girls soccer play to draw -- Observer Preps

Allie Wilson's goal in the second half helped the Blue Darters secure a tie with the Warriors.

Sports
Game Film

By Steven Ryzewski |
October 30, 2015

SIDELINES: Mid-Florida Pop Warner Championships set for Oct. 31

Sports

By Eric Gutierrez |
July 31, 2019

New exhibition opening in SoBo Gallery

The SoBo Gallery will be hosting a reception August 1 to celebrate the opening of the Water Works Exhibition.

West Orange Times & Observer
News

By Eric Gutierrez |
February 29, 2020

PHOTOS: Fifth annual Windermere Fine Arts Show

The annual art show took over downtown Windermere Feb. 29 to March 1.

Southwest Orange
News

By Steven Ryzewski |
January 12, 2018

PHOTOS: Windermere girls soccer takes on Apopka | Observer Preps

The Wolverines were unable to keep pace with the host Blue Darters, suffering just their third loss of the season.

Sports

By Steven Ryzewski |
April 19, 2017

Photos: Olympia tops Dr. Phillips 5-1 in rivalry game -- Observer Preps

A four-run third inning elevated the Titans to victory on their home field.

Sports
Game Film

By Michael Eng |
May 15, 2025

Toll Road Brewing to throw Family Fun Day party

The bash takes place from 1 to 4 p.m. Sunday, May 18, at the brewery, 101 W. McKey St., Ocoee.

Arts + Entertainment
Things to Do

By Michael Eng |
October 22, 2024

Winter Garden to host Health & Harvest Festival

The free event will take place from 8 a.m. to 1 p.m. Saturday, Nov. 2, at the Downtown Pavilion, 104 S. Lakeview Ave., Winter Garden.

Arts + Entertainment
Things to Do

By Liz Ramos |
December 1, 2025

Road work to take place in Windermere

Construction will occur on Butler Street and 7th Avenue from Monday, Dec. 1, through Friday, Dec. 5.

Southwest Orange
News

By Michael Eng |
October 30, 2025

Stoneybrook West Golf Club celebrates season with Fall Festival

This event takes place from 3-10 p.m. Saturday, Nov. 1, and noon to 6 p.m. Sunday, Nov. 2, at 15501 Towne Common Blvd., Winter Garden.

Arts + Entertainment
Things to Do

By Michael Eng |
January 15, 2026

Live Well in Horizon West set for Sunday

The event takes place from 9 a.m. to 1 p.m. Sunday, Jan. 18, in the Hamlin Green Space, 14111 Shoreside Way, Winter Garden.

Arts + Entertainment
Things to Do

By Leticia Silva |
March 18, 2026

Easter Egg Hunt to take place at Roper YMCA

The event will take place from noon to 1 p.m. Saturday, March 21, at 100 Windermere Road, Winter Garden.

Arts + Entertainment
Things to Do

By Observer Staff |
June 5, 2012

Grand Re-opening of The Tiffany Deli

Bobby Simmons held a grand re-opening party on Park Ave. in Winter Park for The Tiffany Deli on Friday, June 1, 2012. Free food, desserts, wine and music were enjoyed by party goers.

Winter Park - Maitland Observer
Neighborhood

By Zak Kerr |
July 16, 2015

Cops Corner 07.16.15

West Orange Times & Observer
News

By Isaac Babcock |
October 13, 2010

Wildcats still undefeated

Brandon Brown-Dukes and Sam Richardson lead Winter Park to a stunning win over Timber Creek

Winter Park - Maitland Observer
Sports

By Steven Ryzewski |
November 25, 2014

ON THE PITCH: Prep soccer news & notes for 11.26.14

Sports

By Michael Eng |
October 22, 2024

Winter Garden PAL rolls with annual Donut Dash 5K

The Winter Garden Police Athletic League’s 2024 Donut Dash is set for 8 a.m. Saturday, Nov. 2, beginning at 1 Surprise Drive, in downtown Winter Garden.

Arts + Entertainment
Things to Do

By Megan Bruinsma |
September 27, 2025

WEEK 6: Friday night football games in review

Do you need an update on high school football? Here’s an overview on how West, Southwest Orange high school football teams competed Friday.

Sports
High Schools

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