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Arts + Entertainment | Things to Do

    By
  • 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.

  • Southwest Orange
  • 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.

  • Arts + Entertainment
  • Things to Do
    By
  • 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.

  • Arts + Entertainment
  • Things to Do
    By
  • 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.

  • Arts + Entertainment
  • Things to Do
    By
  • 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.

  • Arts + Entertainment
  • Things to Do
    By
  • 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.

  • Arts + Entertainment
  • Things to Do
  • 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.

  • Arts + Entertainment
  • Things to Do
  • 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.

  • Arts + Entertainment
  • Things to Do
  • 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.

  • Arts + Entertainment
  • Things to Do
  • 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
  • Things to Do
  • By Observer Staff
  • May 6, 2026
FIT 407 to jumpstart Mother’s Day weekend with pop-up event

The event takes place from 8:30 a.m. to 1 p.m. Saturday, May 9, at Fit 407, 16406 New Independence Parkway, Winter Garden.

  • Arts + Entertainment
  • Things to Do
  • By Observer Staff
  • May 6, 2026
Latin-themed fiesta will heat up Flamingo Crossings

The event takes place from 6 to 9 p.m. Friday, May 8, at Flamingo Crossings in Horizon West.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • April 29, 2026
Winter Garden VFW saddles up for Derby Day

The event will take place from 5 to 9 p.m. Saturday, May 2, at the post, 1170 E. Plant St., Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • April 29, 2026
Ocoee plans Cinco de Mayo fiesta

The city’s Cinco De Mayo Block Party takes place from 6 to 9 p.m. Friday, May 1, in downtown Ocoee.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • April 29, 2026
Shop ’til you drop this weekend in Winter Garden

Downtown Winter Garden will host its Shop, Dine and Stroll event from 9 a.m. to 10 p.m. Saturday, May 2, in downtown Winter Garden.

  • Arts + Entertainment
  • Things to Do
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