Your Town | Southwest Orange

Southwest Orange | Your Town

Megan Bruinsma
November 19, 2025

Orlando Ballet School debuting for the Arts at the J

Orlando Ballet School trainees are bringing their talents to the community in the inaugural opening at JCC.

Southwest Orange
Your Town

Michael Eng
November 11, 2025

Challenge 22’s ninth annual Ruck Walk is Saturday

The annual event takes place from 9 a.m. to 1 p.m. Saturday, Nov. 11, beginning at 8 N. Highland Ave., Winter Garden.

Arts + Entertainment
Things to Do

Michael Eng
November 11, 2025

West Orange Habitat for Humanity sets stage for 2025 Rock the House

Rock the House: An Evening Among the Groves takes place from 6-9 p.m. Saturday, Nov. 15, at the McKinnon Grove Family Farm, 1401 Williams Road, Winter Garden.

Arts + Entertainment
Things to Do

Michael Eng
September 23, 2025

West Orange High School's Class of 1976 plans football party

Reservations are required; please contact Mari Underwood Van Dyke before Oct. 4 at (407) 227-8361.

Arts + Entertainment
Things to Do

Michael Eng
September 17, 2025

West Orange High School Class of 1990 plans reunion

In keeping with good school spirit, the class also is welcoming members of the classes of 1989 and 1991 to join the fun.

West Orange Times & Observer
Your Town

Michael Eng
September 10, 2025

Windermere to host 9/11 sunset service

The town will honor the families and first responders whose lives were forever changed that day.

Arts + Entertainment
Things to Do

Michael Eng
September 2, 2025

West Orange Junior Service League member spearheads hygiene kit drive for local middle schools

The West Orange Junior Service League is proud to celebrate the compassion and leadership of one of its own.

Observer School Zone

Michael Eng
August 26, 2025

Win tickets to Chris Brown, Andrea Bocelli

You can score tickets to two of the hottest upcoming shows and support the Winter Garden Art Association and SOBO Art Gallery at the same time.

Arts + Entertainment
Things to Do

Michael Eng
August 26, 2025

SAVE THE DATE: Windermere High Fall Bash set for Sept. 17

Attendees will enjoy drinks, food, music and a silent auction — all to raise funds for faculty and club grants for the school.

Arts + Entertainment
Things to Do

Michael Eng
August 5, 2025

Observer wins awards for journalism, advertising

The West Orange Times & Observer and Southwest Orange Observer won awards for its journalism, design and advertising at the 2025 Florida Media Conference.

West Orange Times & Observer
Your Town

Sam Albuquerque
July 24, 2025

Match play magic: Fundraiser pits golfers against NBA legends

Headlined by Hall-of-Fame basketball player Vince Carter, Windermere Elementary’s first fundraising tournament offers golfers the chance to play 18 holes against former Orlando Magic players.