Arts + Entertainment

November 28, 2025

Williams Holiday House opens for Christmas

People can begin touring the front yard of the house to see the annual holiday displays at 6 p.m. Friday, Nov. 28.

November 25, 2025

Winter Garden, Ocoee fire departments help Santa come to town

Winter Garden’s Santa Run and Ocoee’s Operation Santa bring joy to the community.

November 17, 2025

VFW Post 4305 to host annual turkey shoot

The turkey shoot will be from 10 a.m. to 2 p.m. Sunday, Nov. 23, at 1170 E. Plant St., Winter Garden.

November 6, 2025

SOBO Art Gallery presents "Home for the Holidays"

The opening reception is 5:30 to 8 p.m. Thursday, Nov. 6, at SOBO Art Gallery.

November 6, 2025

SAVE THE DATE: Ocoee Music Fest returns Nov. 14 and 15

This year’s festival includes performances by The Romantics, John Cafferty and the Beaver Brown Band, Brothers Osborne Dillon Carmichael and more.

November 2, 2025

West Orange, Southwest Orange bands perform at Florida Bandmasters Association 2025 District 8 MPA

All public school marching bands from West Orange and Southwest Orange showcased their 2025 field shows at the event.

October 23, 2025

PHOTOS: Windermere High competes at 2025 Bands of America Orlando Regional Championship

The Fightin’ Wolverine Band and Guard competed against some of the best bands in the country.

October 23, 2025

Windermere Wine & Dine under new leadership

West Orange Foundation takes over Windermere Wine & Dine to elevate the event while maintaining its quality and mission.

October 8, 2025

Oakland Nature Preserve carves out Halloween tradition

Oakland Nature Preserve’s popular Pumpkin Glow is set for later this month. There still is time to carve your own entry for this year’s event.

October 7, 2025

Warriors on Water plans Wellness Day

The second Paddling Through Healing Waters will be from 10 a.m. to 2 p.m. Saturday, Oct. 11, at the Dr. P. Phillips YMCA Family Center.

October 2, 2025

West Orange High School band to host Westside Showcase

The marching band show will take place Saturday, Oct. 18, at Raymond Screws Stadium, 1625 Beulah Road, Winter Garden.

October 2, 2025

Oakland to host Music Under the Oaks event

The town of Oakland will host an '80s and '90s themed event from 6 to 8 p.m. Saturday, Oct. 11, at VanderLey Park, 117 E. Gulley Ave., Oakland.

October 2, 2025

Windermere Brewing Company to celebrate Oktoberfest

The event takes place Oct. 3-5 at the brewery, 111 W. Fifth Ave., Windermere.

September 24, 2025

Peace on Earth: Winter Garden Heritage Foundation, Opera Orlando partner for 'All is Calm' performance

The Winter Garden Heritage Foundation and Opera Orlando will present “All is Calm: The Christmas Truce of 1914,” in December.

September 23, 2025

Season Fall/Winter 2025-2026

Welcome to the Observer's guide to arts and society in Central Florida.

September 19, 2025

Opera’s greatest love story comes to Steinmetz Hall

LA BOHÈME is the definitive depiction of the joys and sorrows of love and loss, and this production transports this beloved story from Paris, France, to the “Paris of the East,” 1930s Shanghai.

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.

August 21, 2025

Sisaundra Lewis to perform at Judson’s Live

The Central Florida native — and one-time Winter Garden resident — was a contestant on ‘The Voice.’

August 20, 2025

Magical Dining 2025: All you need to know

West Orange and Southwest Orange foodies have a plethora of local options in this year’s Magical Dining.

August 7, 2025

Dance community swings into Winter Garden

The West Orlando Westies is dedicated to teaching swing dancing in a community-based environment.

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