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Arts + Entertainment

    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
    By
  • Michael Eng
  • April 29, 2026
Arts at the J to boogie with AARP Orlando Salsa Celebration

This event takes place from 2 to 4:30 p.m. Sunday, May 3, at the Pargh Event Center at the Rosen JCC, 11184 S. Apopka-Vineland Road, Orlando.

  • Arts + Entertainment
  • Things to Do
    By
  • 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
    By
  • 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
    By
  • Leticia Silva
  • April 27, 2026
West Orange High to present 'Newsies'

Performances will take place from Thursday, April 30, to Sunday, May 3, at 1625 Beulah Road, Winter Garden.

  • Observer School Zone
  • News
    By
  • Michael Eng
  • April 23, 2026
Rosen JCC to present Israel North to South

The event takes place from 3:30 to 6:30 p.m. Sunday, April 26, at the Rosen JCC, 11184 S. Apopka-Vineland Road, Orlando.

  • Arts + Entertainment
  • Things to Do
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Latest News Arts + Entertainment

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Pure Barre opens in Downtown Winter Garden
2
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Registration extended for Ocoee PD's Senior Scam Prevention event
3
  • May 8, 2026
District 1 Youth Leadership Council accepting applications
4
  • May 8, 2026
Pedestrian bridge in Windermere to close temporarily
5
  • May 7, 2026
Winter Garden seeks input on Comprehensive Plan update

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