Destinations Downtown Sarasota

First Friday Sip & Shop

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, 1600 blocks of Main Street, Palm Ave., 1st & 2nd 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.


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Sarasota DOG-A-WEEN COSTUME Contest

Mark your calendar for the 15th Annual event Saturday, October 28, 2023

The Annual Dog-A-Ween costume contest returns Saturday, October 28th to the Sarasota Farmers Market Halloween Festival. All proceeds benefit the Donte’s Den Foundation. Guest moderator: Tyler Butler with Out & About.  The judges for the 15th annual event will be Mayor TBD, ABC 7’s Chief Meteorologist Bob Harrigon and Marsha Panuce, founder of Donte’s Den Foundation.  

  • $15 Registration Fee
    9:00 – 9:45 AM CHECK-IN and get your entry number at Lemon Ave. & 1st Street Downtown Sarasota.
  • The Dogs will parade through the Farmers Market towards Paul Thorps Park where the contest will be held
  • Parking is available in Whole Foods Parking Plaza.
  • 10 AM PARADE & 10:15 AM CONTEST


9:00 – 9:45 a.m. register & collect your entry number at Lemon Ave. & Whole Foods downtown Sarasota. Parking is available in Whole Foods Parking Plaza.  The dogs will then parade through the Farmers Market to Paul Thorps Park.  The contest begins at 10 a.m.  When the contest is over, show off your pup costume along Main Street.  Enjoy pet-friendly patios,  indulge in sweet treats, and walk the beautiful bayfront.


    • Dogs must be on a leash at all time
    • No retractable leashes allowed
    • Out of due caution & concern for others, well behaved dogs only
    • Have your dog go potty before arrival

Le Marche Parisian-Inspired Marketplace

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!  Admission is free and the event is open to the public.

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 in JD Hamel Park

Outdoor gallery showcase

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 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. The event is produced by Paragon Festivals and hosted by the Sarasota Downtown Merchants.

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Sarasota Christmas Tree Lighting

Thursday, December 1, 2022 in Five Points Park

Join the celebration

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.


Enjoy refreshments, holiday carols, and photos with Santa! The Christmas Tree will be lit at 7 PM where photos can be taken.  Facebook live coverage sponsored by Out & About Sarasota with Tyler Butler.


Come early and stroll downtown’s many gift stores!  Toys for Tots boxes will be available throughout the downtown district thru December 15th.

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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.Become A Sponsor! Call Ron Soto at (941) 321-0562

The actual pineapple drop is the highlight of a party that includes a wide range of entertainment and attractions throughout the day, starting from 1:00 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, Chas 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. 

Sarasota, Florida New Year’s Eve 2020 Pineapple Drop Block Party – YouTube. 

The Sarasota Dog-A-Ween Costume Contest at the Farmers Market Downtown

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