Explore Downtown Sarasota

First Friday Sip & Shop

October 2022 – May 2023

The Sarasota Downtown Merchants ‘First Friday Sip & Shop’ event is set for every 1st Friday from October 7, 2022 thru May 5, 2023 from 5:00 p.m. – 8:00 p.m. along the 1400, 1500 and the 1600 blocks of Main Street.  The event is open to the public. 

Stroll trendy fashion boutiques, art galleries, experience wine tastings, and live music throughout Main Street.  Tourist and locals, even the occasional celebrity, enjoy caricatures by as the perfect souvenir, something hand-drawn and one of a kind.

Sarasota ROCKtoberfest

October 14-16, 2022

Paragon Festivals with the Sarasota Downtown Merchants bring an authentic 3-Day Oktoberfest experience coupled with fantastic live musical performances to downtown Sarasota in JD Hamel Park. Admission to this family-friendly event is free!

Festivalgoers will find a wide variety of food plus a German feast fit for King Ludwig himself! Dine on German foods like Schweinshaxe (roasted ham hock), Steckerlfisch (grilled fish on a stick), Wurstl (Sausages), Brezen (pretzels, Knodel (potato or flour dumplings), Kasespatzel (cheese noodles), sweet mustards, sauerkraut, red cabbage and more!

Between performances shop the Marketplace of arts, crafts and select fine products and services.

Sarasota Dog-A-Ween Event

Saturday, October 29, 2022

Goblins and ghoulies, candy corn and cornstalks, doggie costume contests and parades: It’s time for dogs to get a scary groove on and don the Halloween garb. The Sarasota 14th Annual Dog-A-Ween costume contest returns Saturday, October 29th to the Sarasota Farmers Market Halloween Festival. All proceeds benefit the Donte’s Den Foundation. Read more

Le Marche Parisian-Inspired Marketplace

Saturday, November 5 , 2022

Le Marche Bohemien… Re-imaging the world’s resources one artist at a time. A marketplace for eclectic creations and more! Saturday, November 5 from 10AM – 5PM at Five Points Park Downtown Sarasota.

Join us for Downtown Sarasota’s French style Marketplace and see the many talented artists. Enjoy a fun day with refreshments, amazing creations and beautiful music by Michelet Innocent!  Michelet is an International Romantic singer. He sings in French, English, Spanish and Italian in concerts, from the New York Metropolitan Opera, for the UN to a performance for French President Jacques Mitterand’s wife. His sound is a blend of Charles Aznavour, Nat King Cole and Johnny Matthis. 

GPS Address: 100 Central Ave. Sarasota FL 34236

Sarasota Fall Fine Art Festival

November 19-20, 2022


The Sarasota Fall Fine Art Festival returns November 19-20, 2022 for its ninth season.  Whether you are an art collector of wish to find origintal, 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. The event is produced by Paragon Festivals and hosted by the Sarasota Downtown MerchantsRead more…

Sarasota Christmas Tree Lighting Event

Thursday, December 1, 2022

Downtown Sarasota’s Christmas Tree is the perfect backdrop for your holiday snapshot. The annual tree lighting event will take place Thursday, December 1st from 6 – 8 PM in Selby Five Points Park, located across the street from the Selby Public Library. Holiday Performance by Ring Sarasota. Enjoy refreshments, music, and photos with Santa! The Christmas Tree will be lit at 7 PM where photos can be taken.

Sarasota New Years Eve Pineapple Drop Block Party

Saturday, December 31, 2022 from 1PM to 1AM
The big New Year’s Eve party in Sarasota is the annual Pineapple Drop Block Party! The dropping of the big glowing pineapple comes at midnight and takes place at the intersection of Lemon Avenue and Main Street in downtown.
The actual pineapple drop is the highlight of a party that includes a wide range of entertainment and attractions throughout the day, starting from 1:0.0 p.m. and running right through until 1:00 a.m. on new years day morning.  There will be live music, with DJs and bands performing, carnival rides, games for the kids and of course plentiful food and drink, with special offers at local bars and restaurants. Live music begins at 9 p.m. on the corner of Main and Lemon Street with performances by 22N, Chaz Collins and SRQ Beats.
Just after the Pineapple Drop there is also a big fireworks display over Sarasota Bay.  This annual event is hosted by the Sarasota Downtown Merchants  🙌 Video from 2017 https://www.youtube.com/watch?v=XBa_QGVkmD8
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