Your Town | Southwest Orange

Southwest Orange | Your Town

Michael Eng
June 9, 2026

Observer wins state awards for advertising, journalism

The West Orange Times & Observer and Southwest Orange Observer won 14 state awards at the 2026 Florida Media Conference.

West Orange Times & Observer
Your Town

Michael Eng
April 29, 2026

Ocoee Police to serve up annual picnic

This event will take place from 11 a.m. to 2 p.m. Saturday, May 2, at Vignetti Park, 1910 Adair St., Ocoee.

Arts + Entertainment
Things to Do

Michael Eng
April 29, 2026

West Orange Junior Service League rides with annual Run of the Roses

This year’s event will take place from 5 to 10 p.m. Saturday, May 2, at Clermont Arts and Recreation Center, 3700 S. U.S. 27, Clermont.

Arts + Entertainment
Things to Do

Michael Eng
March 13, 2026

Here's how to celebrate St. Patrick's Day in Winter Garden, Windermere, Ocoee and Horizon West

As luck would have it, there are five ways to celebrate St. Patrick’s Day this weekend.

Arts + Entertainment
Things to Do

Megan Bruinsma
March 3, 2026

The 2026 Arnold Palmer Invitational kicks off at Bay Hill

The PGA has made its way back to Southwest Orange for competition play from Thursday, March 5, to Sunday, March 8.

Sports

Michael Eng
February 24, 2026

Attention students: Win a $5,000 scholarship from new nonprofit

The Freedom to Think Project currently is accepting submissions for its First Amendment Essay Contest.

West Orange Times & Observer
Your Town

Michael Eng
February 24, 2026

West Orange High charter class to host celebrations

The class will host a Meet and Greet Friday, April 10, at the Winter Garden Heritage Foundation, and a dinner Saturday, April 11, at the West Orange Country Club.

West Orange Times & Observer
Your Town

Michael Eng
February 19, 2026

Three Birds Café supporters plan demonstration

The demonstration is planned for 10:30 a.m. Friday, Feb. 20, outside the cafe, 2 W. Plant St., Winter Garden.

Arts + Entertainment
Things to Do

Michael Eng
February 12, 2026

Windermere rolls out red carpet for Night to Shine

Night to Shine 2026 will take place from 6 to 9 p.m. Friday, Feb. 13, at the church’s Windermere campus, 300 Main St., Windermere.

Arts + Entertainment
Things to Do

Michael Eng
February 5, 2026

Central Florida Chili Cookoff heats up this weekend

This year’s event takes place from noon to 4 p.m. Saturday, Feb. 7, in the Hamlin Green Space, 14111 Shoreside Way, Winter Garden.

Arts + Entertainment
Things to Do

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

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