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Arts + Entertainment | Things to Do

    By
  • Michael Eng
  • January 29, 2026
City Lights Open Mic set for Friday

The event will take place at 9:45 p.m. Friday, Jan. 30, at the West Orange Dream Center, 1136 E. Plant St., Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • January 29, 2026
Town of Oakland to host 26th annual Heritage Day Festival

The event also will feature the Healthy West Orange 5K.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • January 29, 2026
Winter Garden Heritage Foundation ‘paddles up’ for pickleball tourney

Registration is now open for the Paddles for the Past Inaugural Pickleball Tournament, which will take place Saturday, Feb. 28, at both the Roper YMCA Family Center and the Dr. P. Phillips YMCA Family Center.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • January 29, 2026
Windermere to serve up Wine & Dine this weekend

This year’s event takes place from 6 to 9 p.m. Saturday, Jan. 31, at Town Square Park, 520 Main St., Windermere.

  • Arts + Entertainment
  • Things to Do
    By
  • Leticia Silva
  • January 27, 2026
Former Oakland Avenue Charter teacher to perform at Oakland Heritage Day

Kyle Zavada was an Oakland Avenue Charter School music teacher for eight years. This week, he is performing as the opening act at Oakland Heritage Day for the second year.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • January 21, 2026
Islamic center to serve up Orlando Halal Food Festival

The festival takes place from noon to 10 p.m. Saturday, Jan. 24, at the Islamic Center of Orlando, 11543 Ruby Lake Road, Orlando.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • January 21, 2026
Dine al fresco at Windermere’s Food Truck Night

This month’s event takes place from 5:30 to 9:30 p.m. Friday, Jan. 23, at Town Square Park, 520 Main St., Windermere.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • January 21, 2026
Learn more about Oakland Nature Preserve at lunch event

Lunch and Learn will take place from 11:30 a.m. to 1 p.m. Tuesday, Jan. 27, at the Healthy West Orange Heritage and Cultural Center, 21 E. Plant St., Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • January 21, 2026
Bridge Theatre Company to present ‘Anne & Emmett’

The public performance will take place at 2 p.m. Sunday, Jan. 25, at the Pargh Event Center at the Rosen JCC, 11184 S. Apopka-Vineland Road, Orlando.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • January 21, 2026
Lakeview Middle to celebrate library re-opening

The school also will welcome award-winning local author Amar Shah, who will be visiting, speaking with students and signing books.

  • Arts + Entertainment
  • Things to Do
    By
  • Leticia Silva
  • January 20, 2026
Winter Garden to host first cars and coffee of 2026

The event will take place from 8 to 10:30 a.m. Saturday, Jan. 24, at 3118 Daniels Road, Winter Garden.

  • West Orange Times & Observer
  • News
    By
  • Liz Ramos
  • January 19, 2026
Windermere to host first Food Truck Night of the new year

Food Truck Night will be from 5:30 to 9:30 p.m. Friday, Jan. 23, in Town Square Park.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • January 15, 2026
Live Well in Horizon West set for Sunday

The event takes place from 9 a.m. to 1 p.m. Sunday, Jan. 18, in the Hamlin Green Space, 14111 Shoreside Way, Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • January 15, 2026
Dr. Phillips Dance Magnet presents ‘Celebration of Dance’

Celebration of Dance is a fundraising event for the Dr. Phillips High School Dance Magnet.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • January 15, 2026
Windermere plans Arbor Day giveaway

The town will host this event from 9 a.m. to noon, Saturday, Jan. 17, at the Windermere Recreation Center.

  • Arts + Entertainment
  • Things to Do
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