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The Weekly Roundup

This Week's Events

Welcome to your weekly guide to what's happening in Winter Park and nearby neighborhoods.

Each week, you'll find a thoughtfully curated collection of local events, seasonal experiences, and noteworthy happenings, including a few hidden gems you may not find on the usual event calendars.

Whether you're planning the weekend or looking for something new to experience close to home, consider this your invitation to enjoy more of what makes Winter Park such an exceptional place to live.

Never miss what's happening in Winter Park. Get my curated Weekly Events List delivered to your inbox each week, with the events, experiences, and local finds worth having on your calendar.

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This Week's Highlight

Trick or Treat on the Avenue event flyer, Park Avenue, Winter Park

Saturday, October 31, Park Avenue in Winter Park becomes a Halloween celebration: Trick or Treat on the Avenue brings costumed kids and neighbors to the shops along the avenue from 10AM to 12PM for candy, community, and old-fashioned Halloween fun in the heart of Winter Park.

This Week's Fun Things-to-Do:

FRIDAY, OCT. 30TH

HAPPY FRIDAY!

SATURDAY, OCT. 31ST

SATURDAY!

  • Winter Park Farmer’s Market, 8AM-1PM

  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very

  • Epic Paddle Board Adventures, Times & Events Vary

  • Public Ice Skating, Ice Den RDV, Times Vary

  • Fall Bird Migration Walks, Mead Botanical Garden, Winter Park, 8-11AM

  • Yoga in the Park, $15, Mead Botanical Garden, Winter Park, 9-10AM

  • The Flavors of Winter Park Foodie Walking Tour, Winter Park Chamber of Commerce, 10:45AM

  • Dog Day, Harry P. Leu Gardens, Orlando, 9AM-5PM

  • Fall Into The Gardens, Harry P. Leu Gardens, Orlando, 9AM-5PM (everyday until November 2nd)

  • Trick or Treat on the Avenue, Park Ave, Winter Park, 10AM-12PM

  • Goat Yoga, Alaska Farms Orlando, 10:00AM, 11:15AM, & 1:30PM

  • Weekends at the Winery, Lakeridge Winery, 10AM-5PM

  • 6th Annual Fall on the Farm Festival, Amber Brooke Farms, Eustis, 10AM-6PM (Oct.19 – Nov. 22nd)

  • Southern Hill Farms Fall Festival, Lake County, Cleromont, 11AM-5PM

  • Family Highlights Tours, Orlando Museum of Art, Orlando, 1-2PM

  • Saturday Exhibition Highlights Docent-Led Tour, Rollins Museum of Art, Winter Park, 1PM & 3PM

  • Social Hour at the Corner Chophouse, Hannibal Square, Winter Park, 2:30-4PM

  • Imperial on Park: Live Music, Park Ave, Winter Park, 8PM

  • OSC After Dark, Orlando Science Center, 8-11PM

  • WEEKEND OPEN HOUSES, Complete list of Scheduled Open Houses, Various Times

SUNDAY, NOV. 1ST

SUNDAY FUN DAY!

MONDAY, NOV. 2ND

MAGICAL MONDAY

  • Epic Paddle Board Adventures, Times & Events Vary

  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very

  • Fall Into The Gardens, Harry P. Leu Gardens, Orlando, 9AM-5PM (everyday until November 2nd)

  • Free Day & Story Time, Harry P. Leu Gardens, Orlando, 9AM-5PM

  • Social Hour at the Corner Chophouse, Hannibal Square, Winter Park, 4-6PM

  • Audubon Community Market, Audubon Park, 5-9PM

  • C-M Bakari Sour Dough Bread, Audubon Community Market, 5-9PM (Sells Out Fast, Pre-Order Before Event)

  • Orlando Magic vs Washington Wizards, Kia Center, 7PM

  • Shining Starz Karaoke, Aloma Bowl, Winter Park, 7PM

TUESDAY, NOV. 3RD

IT’S TUESDAY!

  • Epic Paddle Board Adventures, Times & Events Vary

  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very

  • Fall Into The Gardens, Harry P. Leu Gardens, Orlando, 9AM-5PM (everyday until November 2nd)

  • Watercolor White Peacock Butterfly, Harry P. Leu Gardens, Orlando, 1-3:30PM

  • Social Hour at the Corner Chophouse, Hannibal Square, Winter Park, 4-6PM

  • Trivia Night!, Bonfire at Winter Park Pines, Winter Park, 7-9PM

  • Tasty Takeover- Food Truck Block Party, The Milk District, Orlando E. Robinson St. 6:30-10PM

  • AJ Chocolate House: Ladies Night, AJ Chocolate House, Park Ave, Winter Park, 6-10PM

WEDNESDAY, NOV. 4TH

WEDNESDAY, LATIN FOR “IT’S ALMOST THE WEEKEND!”

  • Epic Paddle Board Adventures, Times & Events Vary

  • Cakeistry, Glass Knife, Downtown Park Avenue, Winter Park, Times Very

  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very

  • Fall Into The Gardens, Harry P. Leu Gardens, Orlando, 9AM-5PM (everyday until November 2nd)

  • Goat Yoga, Alaska Farms Orlando, 5:30PM

  • Social Hour at the Corner Chophouse, Hannibal Square, Winter Park, 4-6PM

  • Dreamscapes in Encaustic & Mixed Media, Art & History Museums – Maitland, 6-8:30PM

  • Ladies Night, The Wine Room on Park Avenue, 6:30PM

  • Art Night Out, Orlando Museum of Art, 8PM

THURSDAY, NOV. 5TH

THURSDAY: THE DAY THAT SAYS, “YOU GOT THIS!”

  • Epic Paddle Board Adventures, Times & Events Vary

  • Cakeistry, Glass Knife, Downtown Park Avenue, Winter Park, Times Very

  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very

  • Fall Into The Gardens, Harry P. Leu Gardens, Orlando, 9AM-5PM (everyday until November 2nd)

  • Popcorn Flicks in the Park Zootopia, Central Park, Winter Park, 8PM

  • Vinyl Night at The Museum, Orlando Museum of Art, 5-8PM

  • Phat Ash Cookies – Pairing Experience, Simply Cheese, Orlando, 6:30PM

  • Thursday Night Hang, Blue Bamboo Center for the Arts, Winter Park, 8-10PM

FRIDAY, NOV. 6TH

HAPPY FRIDAY!

  • Epic Paddle Board Adventures, Times & Events Vary

  • Scenic Boat Tour Around Winter Park, Morse Blvd, Downtown Winter Park, Times Very

  • Fall Into The Gardens, Harry P. Leu Gardens, Orlando, 9AM-5PM (everyday until November 2nd)

  • Indoor Pickleball Open Courts and Lessons, Gateway Church, Winter Park, 9AM-1PM

  • 16th Annual Veterans Day Celebration, Ruby Ball Amphitheater, Winter Park, 10AM

  • Watercolor Pears, Leu Gardens, 10AM-12:30PM

  • Art Adventures: Habitat Heroes, Orlando Museum of Art, 10:30AM-12PM

  • Southern Hill Farms Fall Festival, Lake County, Cleromont, 11AM-5PM

  • Social Hour at the Corner Chophouse, Hannibal Square, Winter Park, 4-6PM

  • Deland Artisan Alley Farmer’s Market, 6-9PM

  • Sounds of Wekiva, Live Music Event, Wekiva Island, 7PM

  • Shining Starz Karaoke, Aloma Bowl, Winter Park, 7PM

Coming Up:

SAVE THE DATE & BOOK EARLY

SATURDAY-SUNDAY, NOV. 15TH-16TH

WEDNESDAY, NOV. 18TH

NOV. 20 – JAN. 11TH

  • Dazzling Nights, Harry P. Leu Gardens, Orlando, 5-11PM, Nov 20 – Jan 11th

Know an event worth sharing?

Send it my way and it might make next week's roundup. hello@floridalivingwithmelissa.com