Things to Do | Arts + Entertainment

Arts + Entertainment | Things to Do

Justice Covert
May 20, 2026

Comedian Brad Stine to perform in Windermere

Three men’s ministries are trading their annual picnic for a night of stand-up comedy, bringing in the conservative Christian comedian Friday, May 29, at Family Church.

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Michael Eng
May 19, 2026

Woodlawn to honor fallen heroes at 76th Memorial Day Service

This year’s service takes place at 10 a.m. Monday, May 25, at the cemetery, 400 Woodlawn Cemetery Road, Gotha.

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Michael Eng
May 19, 2026

Winter Garden to remember fallen heroes

Winter Garden will host its Memorial Day Community Celebration 2026 from 8:30 to 9:30 a.m. Monday, May 25, at Veterans Memorial Park, 420 S. Park Ave., Winter Garden.

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Michael Eng
May 19, 2026

Ocoee’s Memorial Day Ceremony set for May 21

The event begins at 11 a.m. at Ocoee Lakeshore Center, 125 N. Lakeshore Drive, Ocoee.

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Michael Eng
May 19, 2026

Town of Windermere, Rotary to honor war dead

The Windermere Memorial Day Observance will take place at 10 a.m. Monday, May 25, at Town Hall, 520 Main St. Windermere.

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Leticia Silva
May 13, 2026

West Orange ready to celebrate America's 250th anniversary

As the United States turns 250, cities and towns around the nation are celebrating this milestone. Winter Garden and Hamlin are getting ready for the celebrations with lots of festivities already planned.

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By Observer Staff
May 12, 2026

Oakland Nature Preserve to offer Meditative Hike and Yoga at the Lake

This event takes place from 9 to 11 a.m. Sunday, May 17, at the preserve 747 Machete Trail, Oakland.

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Michael Eng
May 12, 2026

State Rep. Eskamani to host supply drive for former Spirit Airlines employees

The drive takes place from 9 a.m. to 5 p.m. Friday, May 15, at Eskamini’s office, 1507 E. Concord St., Orlando.

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Michael Eng
May 12, 2026

Town of Windermere to host Armed Forces Day 2026

The event will take place at 10 a.m. Saturday, May 16, at Town Hall, 520 Main St., Windermere.

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Michael Eng
May 12, 2026

Ocoee to host 2026 Asian Cultural Festival this weekend

This year’s event will take place from 3 to 8 p.m. Sunday, May 17, at the Ocoee Lakeshore Center, 125 N. Lakeshore Drive.

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Leticia Silva
May 8, 2026

Young Star Musical Theatre presents 'Joseph and the Amazing Technicolor Dreamcoat'

The musical performance will take place Friday, May 8, Saturday, May 9, Friday, May 15, and Saturday, May 16.

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By Observer Staff
May 6, 2026

Winter Garden Heritage Foundation to host Heritage Happy Hour

The event will take place from 5 to 7:30 p.m. Wednesday, May 13, at Heller Hall, 21 E. Plant St., Winter Garden.

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By Observer Staff
May 6, 2026

Opera Orlando celebrates end of 10th season with concert

This one-night-only concert will have you singing along with selections from Rigoletto, The Magic Flute, La Traviata, Carousel, Les Miserables, and much, much more.

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By Observer Staff
May 6, 2026

Hamlin saddles up for 2026 Hoedown

The Hamlin Hoedown will take place from 10 a.m. to 2 p.m. Saturday, May 16, in the Hamlin Green Space, 14111 Shoreside Way, Winter Garden.

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By Observer Staff
May 6, 2026

Treat your mom to a Wine Walk this weekend

This event will take place from 5:30 to 7:30 p.m. Saturday, May 9, at Southern Hill Farms, 16651 Schofield Road, Clermont.

Arts + Entertainment
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