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10 can't-miss events on Longboat Key in 2023

Mark your calendars. These are the top 10 events for the year on Longboat Key.

The Krohn family set up their VIP tables with settings for everyone.
The Krohn family set up their VIP tables with settings for everyone.
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Longboat Key is a busy island once the snowbirds land. Social calendars fill up quickly, so make sure to pencil these 10 events into your 2023 calendars. 

Savor the Sounds

The three-part concert series will be held at the Town Center Green. The "elegant picnic" is organized by the Longboat Key Chamber of Commerce. The lawn and bands are provided, the chairs and picnic accouterments are left up to the guests. Publix will be offering boxed dinners that can be ordered ahead of the concert. 

Advanced tickets are $25, and $35 at the door. There are also VIP tables for eight available for $250. 

Steve Cockherham gets his bowtie adjusted by Lesley Rife.
Lord’s Warehouse Fashion Show

On March 9, clothes are headed from the racks to the runway, and then back to the racks again. The Longboat Island Chapel’s consignment shop is hosting their annual garden-themed fashion show. 

Models are allowed to buy one outfit of their choice, but the rest of the clothes, shoes and accessories go back to the store after the show. Be prepared to show off your own style—the best hat wins a prize this year. 

Mary Ruth Meyers stands in the crowd of women's clothing.
Royal Rummage Sale

This event is so popular, there’s a sale and a pre-sale. Those early bird shoppers who can’t bear to miss a bargain can pay $5 to shop early. Volunteers at St. Mary, Star of the Sea Church collect and sort donations all year long. 

The rummage sale is being held March 4-5, and is one of the church's biggest fundraisers. Shop for clothing, furniture, art, collectibles, housewares, jewelry and more.

Biscuit, Tony and Nancy Roberts
Freedom Fest

This is a can’t miss event that you can’t be late to because it starts with “The Shortest Parade in America” on Bay Isles Road. Following the parade, residents are invited to Bicentennial Park for a bite to eat and a butterfly release. 

Freedom Fest has become a Fourth of July Longboat Key tradition. The parade is not just short, it’s adorable thanks to the Rotary Club’s Hot Diggity Dog parade and contest. 

In 2022, Biscuit arrived on a float fashioned into a hot air balloon using an exercise ball. The competition is stiff. To be top dog, start creating your entrance now. 

CEO of The Paradise Center Suzy Brenner lead the LBK Paradise Striders team. 
Breast Cancer Walk

Not a lot of good things came out of the COVID-19 pandemic. But in the midst of shutdowns and cancellations, one can't miss event landed on Longboat: the Making Strides Against Breast Cancer satellite walk. 

2023 will be the third walk TPC has organized. The main event takes place at Nathan Benderson Park in October, but the LBK Paradise Striders team walks from The Paradise Center on Bay Isles Road through the Longboat Key Club's Harbourside neighborhood and back. 

The Rotary Club of Longboat Key will be holding its 10th Veterans Day event in 2023. 
Veterans Day

The Rotary Club of Longboat Key's Veterans Day program is the patriotic can't miss event of the year. Local veterans are honored with music, flags, food, gifts and guest speakers. 

The military singalong is always a highlight, with members of each branch of service standing to belt out each anthem. 2023 marks the tenth anniversary of the event. 

Members of the Ladies Guild craft for months preparing for the annual Christmas Bazaar. 
Christmas Bazaar

It takes a lot of yarn and felt to get a Christmas Bazaar together. The Ladies Guild at St. Mary, Star of the Sea Catholic Church work for months creating and crafting Christmas gifts. 

The bazaar is held in November to give everyone a head start on Christmas shopping. And as of last year, there's a new addition. Shop 'til you drop because the Maine Line food truck will be waiting in the parking lot to refuel you with a lobster roll. 

Choir members from churches all over the island come together to sing for the Interfaith Service. 
Interfaith dinner

There are a half a dozen places to worship from St. Armands Circle to the north end of Longboat Key depending on your religion, but once a year, they all come together as one. The interfaith service and dinner is held the Tuesday before Thanksgiving. 

Each year, a different church or the temple hosts the service and dinner. Everything from dinner to preaching is on a rotation, so each faith is equally represented and the work is shared. Hundreds of people attend the event.  

“I love the interfaith Thanksgiving service,” Rev. David Marshall of All Angels Episcopal Church said. “I love having people get together, all different walks of life, to give thanks.”  

The Breglia family enjoys Light up Longboat.
Photo by Lesley Dwyer
Light up Longboat

As the oak tree grows, so does the party. Light up Longboat is held at the Town Center Green and kicks off the holiday season on Longboat Key by lighting the tree. 

The annual event has everything one could want in a holiday party—Christmas lights, hot chocolate, Santa Claus, candy canes and wine if you pop by the Longboat Key Chamber of Commerce tent.  

Mote Marine Laboratory & Aquarium brings their mascots, Gilly the Shark and Shelley the Sea Turtle. Light up Longboat is fun for all ages. 

Robyn Marin and Amy Goldman know how to accessorize on a sunny day.
Photo by Lesley Dwyer
Lawn Party by the Bay

To be determined if the restaurant tents will be staked into Longboat Key soil, but the Kiwanis Lawn Party still is and always will be a Longboat Key event that you simply can’t miss. 

The Kiwanis Club of Longboat Key organizes it, and even though it was held at Ken Thompson Park in 2022, the Town Center Green hasn’t been ruled out as the 2023 venue. 

"What is most important to our Kiwanis Club is raising the most money for the kids. We feel the best chance at having future success for the Lawn Party is having it at a consistent site that can also handle growth,” President Michael Garey said. “"We are open to returning to Town Center Green. We have reserved Ken Thompson Park just to be sure and because we have heard great comments about not just the space, but also the logistics.”  

The lawn party is held on the first Saturday of December each year and features local food and beverage vendors, live music and a grand prize of $5,000. The event sees from 800 to 900 guests and raised over $90,000 for the Children’s Guardian Fund two years in a row.   



Lesley Dwyer

Lesley Dwyer is a staff writer for East County and a graduate of the University of South Florida. After earning a bachelor’s degree in professional and technical writing, she freelanced for the Sarasota Herald-Tribune. Lesley has lived in the Sarasota area for over 25 years.

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