• Alternate Text
  • Loading

  • Holiday Gift Guide
  • Health Observed
  • Crossword
  • Contests
  • Newsletters
  • e-Newspaper App
  • Longboat
    • News
    • Cops Corner
    • Real Estate
    • Business
    • Neighbors
    • Opinion
  • East County
    • News
    • Real Estate
    • Business
    • Neighbors
    • Schools
    • Sports
    • Opinion
  • Sarasota
    • News
    • Cops Corner
    • Real Estate
    • Business
    • Neighbors
    • Schools
    • Sports
    • Opinion
    • Siesta Key
  • Arts + Entertainment
    • Eat + Drink
    • Arts + Culture
    • Reviews
    • Things To Do
    • Black Tie
    • Spotlight Partners
  • LWR Life
  • Galleries
  • More
    • Hurricane Season
    • Red Tide Map
    • Health Observed
    • Sand Bucket List
    • Calendar
    • Celebrations
    • Contests
    • Tributes
    • Submit a Celebration
    • Submit a Tribute
    • Public Notices
    • Classifieds
  • Longboat
    • Longboat
    • News
    • Cops Corner
    • Real Estate
    • Business
    • Neighbors
    • Opinion
  • East County
    • East County
    • News
    • Real Estate
    • Business
    • Neighbors
    • Schools
    • Sports
    • Opinion
  • Sarasota
    • Sarasota
    • News
    • Cops Corner
    • Real Estate
    • Business
    • Neighbors
    • Schools
    • Sports
    • Opinion
    • Siesta Key
  • Arts + Entertainment
    • Arts + Entertainment
    • Eat + Drink
    • Arts + Culture
    • Reviews
    • Things To Do
    • Black Tie
    • Spotlight Partners
  • LWR Life
  • Galleries
  • More
    • More
    • Hurricane Season
    • Red Tide Map
    • Health Observed
    • Sand Bucket List
    • Calendar
    • Celebrations
    • Contests
    • Tributes
    • Submit a Celebration
    • Submit a Tribute
    • Public Notices
    • Classifieds
  • Holiday Gift Guide
  • Health Observed
  • Crossword
  • Contests
  • Newsletters
  • e-Newspaper App

Sarasota celebrates new year with a street party downtown

Revelers of all ages enjoy fun, games, food at the city's annual Pineapple Drop festivities.


  • By Eric Garwood
  • | 9:04 a.m. January 1, 2020
  • Sarasota
  • Neighbors
  • Share

Thousands packed Main Street on New Year's Eve for the Downtown Sarasota Block Party and Pineapple Drop Celebration. 

Food, games, live music, carnival rides and more made the evening fun for people of all ages hours before the pineapple descended, ringing in 2020. 

From Five Points Park back toward Orange Avenue, fun lovers challenged a mechanical bull, a rock-climbing wall, a bungee jump, tame (and otherwise) rides and games of skill. Some, though, just pulled up a chair and watched it all take place, listening to live music throughout the event.

Meanwhile, at Marie Selby Botanical Gardens . . . 

 

Ross and Korey Toepel celebrated the new year with friend Mike Weber, visiting from Pittsburgh.
Ross and Korey Toepel celebrated the new year with friend Mike Weber, visiting from Pittsburgh.
The pineapple was a star attraction.
The pineapple was a star attraction.
John and Debbie Nielsen, left, Joyce Gaffney, and Pam and Wayne Jones celebrated with 2020 vision.
John and Debbie Nielsen, left, Joyce Gaffney, and Pam and Wayne Jones celebrated with 2020 vision.
New Year's Eve literally had its ups and downs for Kadee Engle of Punta Gorda, who tried out the bungee-bouncing attraction.
New Year's Eve literally had its ups and downs for Kadee Engle of Punta Gorda, who tried out the bungee-bouncing attraction.
Anastasia Nersesov, from Chicago, challenged the rock-climbing wall with a smile on her face.
Anastasia Nersesov, from Chicago, challenged the rock-climbing wall with a smile on her face.
The tea cup ride was popular with children.
The tea cup ride was popular with children.
Some of the prizes to win at the carnival games.
Some of the prizes to win at the carnival games.
Cal and Ivey Dabbs came away from a game with a prize.
Cal and Ivey Dabbs came away from a game with a prize.
Some of the carnival rides were tame, and others were not.
Some of the carnival rides were tame, and others were not.
The Christmas tree in Five Points Park.
The Christmas tree in Five Points Park.
Ryleigh McDowell, 4, sat for a face-painting session with her parents nearby.
Ryleigh McDowell, 4, sat for a face-painting session with her parents nearby.
The Ferris wheel rose high above the festivities.
The Ferris wheel rose high above the festivities.
Steve Heinrich and Lisa Wolfe were all smiles.
Steve Heinrich and Lisa Wolfe were all smiles.
Hazel Young took on the mechanical bull ride on Main Street.
Hazel Young took on the mechanical bull ride on Main Street.
Kelly, Duane and Abby Dunn enjoyed the scene alongside Main Street.
Kelly, Duane and Abby Dunn enjoyed the scene alongside Main Street.
Ellis, Alex and Stephanie Israel were all smiles after winning a stuffed toy at a basketball-shooting game.
Ellis, Alex and Stephanie Israel were all smiles after winning a stuffed toy at a basketball-shooting game.
Ruth and Taylor Miller unfolded their chairs on Main Street and listened to live music.
Ruth and Taylor Miller unfolded their chairs on Main Street and listened to live music.
Performer Cha Cha Sunshine dressed as a pineapple.
Performer Cha Cha Sunshine dressed as a pineapple.
Jeanni Castro, an aerialist from the Circus Arts Conservatory, performed above Main Street.
Jeanni Castro, an aerialist from the Circus Arts Conservatory, performed above Main Street.
It's 2020.
It's 2020.

 

Latest News

Evidence discovered in the home of 33-year-old Demond L. Smith who was arrested by Sarasota police on multiple charges.
  • December 20, 2025
Repeat felon faces charges in Sarasota drug bust
Traffic cleared after fire, bridge malfunction in Sarasota, Longboat
  • December 19, 2025
Traffic cleared after fire, bridge malfunction in Sarasota, Longboat
District 5 representative Ron Cutsinger will be the 2026 chairman of the Sarasota County Commission.
  • December 19, 2025
Sarasota County commissioners pick chair, vice chair
Locations of the new St. Armands speed tables are marked in red.
  • December 19, 2025
St. Armands speed humps will be replaced with permanent speed tables

Sponsored Health Content

Sponsored Content

The best of Your Observer, delivered directly to your inbox

Get the latest in news, sports, schools, arts and things to do in Sarasota, Siesta Key, Longboat Key and East County.

Sign Up

Latest in Neighbors

The home at 2834 Browning Street featured countless decorations and animated figures.
  • December 18, 2025
Sarasota homes light up for the holidays
Osprey play an important role in local ecosystems, and they seek out high perches on either designated nesting perches or, as in this case, power poles.
  • December 18, 2025
Ospreys get a home renovation
Emily Chana, 10, rehearses the swinging trapeze.
  • December 17, 2025
Sailor Circus Academy students prepare for 'Winter’s Dream' show
Sixth grader Stella Schechter holds up a finished craft for David Stone.
  • December 16, 2025
Emanu-El students celebrate Hanukkah with Aviva Senior Living residents
Kindergartener Santiago Perez checks out the crochet items.
  • December 16, 2025
Holiday House SRQ now serves a fifth school, but holiday shopping costs rise
Zac Boone, 6, showcases his crystals.
  • December 15, 2025
Children's Entrepreneur Market offers kids business experience

App

Download the Your Observer app

Stay in the know with the latest local news. Any device, anytime, anywhere.

DOWNLOAD NOW

Contact

  • 1970 Main St.
  • Third Floor
  • Sarasota, FL 34236
  • Phone: 941-366-3468
  • FPN Verified

Extra, Extra!

  • Newsletters
  • App
  • Crossword
  • Contests

more

  • About Us
  • Contact Us
  • Classifieds
  • Advertise
  • Rack Locations
  • Jobs
  • Privacy Policy
  • Accessibility Options

sister sites

  • Business Observer
  • Jax Daily Record
  • Orange Observer
  • Accessibility Options
  • Copyright © 2025 Observer Media Group Inc., All Rights Reserved
Sign Up for Daily Headlines

A daily dose of news from Longboat Key, East County, Sarasota and Siesta Key.

Sign Up for In Case You Missed It

A Saturday dose of the week's top stories from Sarasota, Longboat Key and East County.


The Your Observer App is Here!

Get local news you can trust — now on your phone, tablet or laptop. Fast. Free. Easy to Use.
Stay informed, wherever you are.

Download Now