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Arts + Entertainment

    By
  • Michael Eng
  • November 6, 2025
Winter Garden Rotary goes all in on poker tournament

The club’s 17th annual Texas Hold ‘Em Poker Tournament takes place at 7 p.m. Friday, Nov. 7, at Tanner Hall, 29 W. Garden Ave., Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Leticia Silva
  • November 4, 2025
Winter Garden Hypnosis to host Power of Connection weekend

The event will take place from 9 a.m. to 5 p.m. Friday, Nov. 7 to Sunday, Nov. 9 at Flamingo Crossings, 13295 Hartzog Road, Winter Garden.

  • Southwest Orange
  • News
    By
  • Megan Bruinsma
  • November 4, 2025
Ocoee Fire Department hosting an open house

The City of Ocoee’s Fire Department is hosting its annual open house Saturday, Nov. 8.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • 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.

  • West Orange Times & Observer
  • News
    By
  • Leticia Silva
  • October 31, 2025
Healthy West Orange to host annual Health & Harvest Festival

The event will take place from 8 a.m. to 1 p.m. Saturday, Nov. 8, at Winter Garden’s farmers market.

  • West Orange Times & Observer
  • Neighborhood
    By
  • Michael Eng
  • October 30, 2025
Town of Windermere to host first Lakes Cleanup Day

The cleanup begins at 1:15 p.m. Sunday, Nov. 2, at Fernwood Park, 632 Butler St., Windermere.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • October 30, 2025
West Orange chamber tees off with Fall Golf Classic

The tournament takes place at 9 a.m. Monday, Nov. 3, at West Orange Country Club, 3300 West Orange Country Club Drive, Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • October 30, 2025
Stoneybrook West Golf Club celebrates season with Fall Festival

This event takes place from 3-10 p.m. Saturday, Nov. 1, and noon to 6 p.m. Sunday, Nov. 2, at 15501 Towne Common Blvd., Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • October 30, 2025
Spooky Caboose chugs into downtown Winter Garden

The Winter Garden Heritage Museum will host a special event to celebrate Halloween from 3-8 p.m. Friday, Oct. 31, at 21 E. Plant St., Winter Garden.

  • Arts + Entertainment
  • Things to Do
    By
  • Leticia Silva
  • October 28, 2025
Animal Clinic of Windermere to host annual open house

Open house will take place from 10 a.m. to 2 p.m. Saturday, Nov. 1, at 1909 Maguire Road, Windermere.

  • Southwest Orange
  • News
    By
  • Megan Bruinsma
  • October 28, 2025
Run, ruck or walk for veterans in Horizon West American Legion’s 5K

The Veteran’s Appreciation 5K Fun Run will take place at Home State Brewing Co. in Horizon West.

  • Arts + Entertainment
  • Things to Do
    By
  • Leticia Silva
  • October 28, 2025
Rotary Club of Dr. Phillips to host annual tasting event

The Taste of Dr. Phillips will take place from from 1 to 4 p.m. Sunday, Nov. 2 at 7958 Via Dellagio Way, Orlando.

  • Southwest Orange
  • News
    By
  • Megan Bruinsma
  • October 27, 2025
Philly Pretzel Factory coming to Winter Garden

The pretzel shop from Philadelphia will be in the Avamar Crossing shopping plaza.

  • West Orange Times & Observer
  • News
    By
  • Megan Bruinsma
  • October 24, 2025
Lego day in Winter Garden

The Central Florida Railroad Museum will display a Halloween and Holiday-themed Lego model railroad.

  • Arts + Entertainment
  • Things to Do
    By
  • Michael Eng
  • 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.

  • Observer School Zone
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