DSEA First Friday Sip & Shop

The First Friday event runs along the 1400, 1500, 1600 blocks of Main Street, Palm Ave., 1st & 2nd Street. Prepare to be mesmerized by the array of upscale art, home decor and fashion boutiques, each offering their own unique style and collections.

Sarasota Rocktoberfest

October 13-15, 2023

Authentic 3-Day Oktoberfest experience coupled with fantastic live musical performances, downtown Sarasota in JD Hamel Park. Admission to this family-friendly event is free!

St. Armands Fall Festival of the Arts

If you are looking for art to beautify your home or office or just be inspired, then come to the St. Armands Fall Festival of the Arts on October 21-22, 2023. The event is produced by Paragon Festivals and hosted by the Downtown Sarasota Enrichment Association. The event is held in St. Armands Circle Park located in St. Armands Circle. 

Dog-A-Ween Costume Contest

Saturday, October 28, 2023. Are you ready to embark on an exciting journey filled with wagging tails, adorable costumes, and heartwarming compassion? We’re thrilled to invite you to the 16th Annual Sarasota DOG-A-WEEN COSTUME Contest, an event that promises to bring joy, laughter, and a sense of community like no other.

LeMarche Parisian Outdoor Marketplace

Saturday, November 4, 2023

Prepare to embark on a sensory journey into a realm of creativity and craftsmanship that will leave you inspired and awestruck. On Saturday, November 4, 2023, Sarasota’s Five Points Park will transform into a captivating tapestry of artistic expression, as the LeMarche Parisian Outdoor Marketplace makes its triumphant return.

Sarasota Fall Fine Art Festival

November 18-19, 2023

The Sarasota Fall Fine Art Festival returns November 18-19, 2023 for its tenth season.  Whether you are an art collector or wish to find original, creative handmade arts and fine crafts for home or office, come see the palette of art the event will lay for you.   This fine art festival is held in downtown Sarasota in JD Hamel Park at Gulfstream and Main Street.

Sarasota Food Truck Rally & Music Festival

Friday, November 24th.

Sarasota, get ready to spice up your November with the Food Truck Rally & Music Festival at J.D. Hamel Park! This unforgettable event kicks off on Friday, November 24th, when from 4pm to 10pm, you can treat your taste buds to a variety of culinary delights.

Downtown Sarasota’s Enchanting Christmas Tree Lighting

Thursday, November 30, 2023

Mark your calendars for Thursday, November 30th, from 6 to 8 PM, as Selby Five Points Park becomes the backdrop for a magical evening of joy, music, and festive lights. Join us in the heart of Downtown Sarasota, as the Selby Five Points Park transforms into a holiday haven, complete with the majestic centerpiece—the dazzling Christmas Tree.

Siesta Beach Seafood & Music Festival

December 1st – 3rd

Come share in the festivities of the 5th Annual Siesta Beach Seafood & Music Festival in Siesta Beach, FL. The event sets up on the Siesta Key Pavilion and runs December 1-3, 2023 and is graciously hosted by Sarasota County.

SRQ NYE Pineapple Drop

Celebrate the last day of 2023 in Downtown Sarasota with thrilling midway rides and games for all ages and your favorite fair food, live music and DJs, special offers at local bars and restaurants, and the annual Pineapple Drop followed by a fireworks display over Sarasota Bay.  Event admission is free. 

Sarasota Seafood & Music Festival

Time to get back outdoors and enjoy a weekend of pure relaxation full of great food and wonderful live music.  January 26th-28th, 2024 in JD Hamel Park – the 8^th  annual Sarasota Seafood & Music Festival. Fun, food, festivities and relaxation

begin Friday evening 4-10pm, continuing Saturday 11-10 and Sunday 11-6.  The event is produced by Paragon Festivals, hosted by the Downtown Sarasota Enrichment Association with the Humane Society of Sarasota County the event’s Special Guest.  General admission is FREE!!! 

Sarasota Festival of the Arts

Looking ahead for fun things to do? Please put us on your “To Do” list on February 24-25, 2024 in JD Hamel Park: the premiere of the Sarasota Festival of the Arts. The event will showcase the original works of artisans and crafters from throughout Florida and across the United States. The event is graciously hosted by the Downtown Sarasota Enrichment Association.