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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.

 

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