Upcoming Fall and Winter Events Near Siesta Key

Cool Off With These Cool Events

That’s a wrap for summer on Siesta Key – the temperatures are cooling and the kids are heading back to school. While the season might be winding down, a new one is starting, and it’s full of fun Siesta Key events and things to do.

Try your first triathlon, enjoy a spine-chilling Halloween event, or usher in the Christmas season this year while staying at one of our Siesta Key resort rentals. With events and activities for the whole family, you’re bound to have a fun and relaxing post-summer vacation on the Key.

Here are just a few from the long list of events around the corner:

Siesta Key Triathlon

athlete swimming in the water

For vacationing athletes, the annual Siesta Key Triathlon is a fun event to watch – or to compete in.

The race involves a 0.3-mile swim in the coastal waters off Siesta Beach, a 13-mile bike ride around the south end of the island, and a three-mile out-and-back run along the hard-packed sands of Siesta Beach.

This event has been running for 24 years and is a fundraiser for the Sarasota YMCA Sharks Swim Team. The race begins at 7 a.m. on September 22 near the lifeguard stations on Siesta Beach.

Fright Night on St. Armands Circle

As summer winds, people across North America have a different holiday on their minds: Halloween.

Sarasota County has a number of Halloween events to choose from, but perhaps the most-awaited is the annual Fright Night at St. Armands Circle. Expected storefronts to be filled with cobwebs, brooms, and ghoulish faces. In the circle, characters from your worst nightmares will lurk around every corner.

Kids should come dressed to impressed, as they can trick-or-treat from shop to shop. Restaurants and vendors will have special Halloween promotions, and visitors can watch a special performance of “Thriller” put on by a local high school – and annual tradition.

Come celebrate the spookiest holiday of the year this October 31 at St. Armands, just a 20-minute drive north of Siesta Key. This also gives vacationers a chance to check out Siesta’s sister islands to the north, Bird Key, Lido Key, and Longboat Key.

Siesta Key Crystal Classic Sand Sculpting Competition

Each year, some of the best sand artists from around the world travel to Siesta Key, FL, to compete for a grand prize. The Siesta Key Crystal Classic is a professional-level sand sculpting competition that draws artists from different corners of the world.

While only 20 to 25 master sculptors compete, thousands to come watch every year – and with good reason.

 If you thought your sand castles were good, these sand sculptures will blow your mind. Expect towering Tritons, nods to the U.S. army, a VW Volkswagen, and, of course, palatial sand castles.

This year, the four-day competition takes place from November 9 to 12. There will be food vendors, live music, and other activities. It’s the perfect family activity.

Light up Siesta Key Village Parade

While it may seem early in the year to be thinking about Christmas, there is so much to do in Siesta Key that time of year, it’s good to start planning.

girl wrapped in a scarf

Ring in the most wonderful time of the year with the Siesta Key Village Parade and Holiday Open House, a time to celebrate the upcoming season with the local community. These Christmas events include the lighting of the village tree, the arrival of Santa Claus, live music, and tasty treats. A parade will proceed down Ocean Boulevard, starting at the Siesta Key Oyster Bar restaurant.

The date for 2018 has yet to be confirmed, but the festivities typically take place at the end of November.

Christmas Boat Parade of Lights

Rounding out the end of the fall season and ushering in winter is the perfect juncture of Christmas and Florida living.

First launched in 1986, the Christmas Boat Parade of Lights sees the boats of Sarasota Bay stringing themselves with lights, ribbons, and holiday cheer parading along the shoreline for all to see. This parade is a magical experience for all – the young and the young at heart.

The pleasant weather this time of year draws thousands. The parade takes place this year on the evening of December 8, beginning at City Island and putters along the mainland’s coast. Unsurprisingly, this on-the-water parade is a favorite among Sarasota and Siesta Key events.

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