Skip to main content

RSW Living Magazine

10 Things To Do In Southwest Florida This October

Looking for something to do in the Month of October? We've got you covered with a wide array of events including festivals, art shows, and more!

Remember to check the event's webpage for changes and cancellations due to COVID before attending.

26th Annual Downtown Sarasota Craft Festival - start Oct 02 2021 1000AM

26th Annual Downtown Sarasota Craft Festival - Oct 02, 2021 10:00AM

Sarasota, located along Florida's Gulf of Mexico is well known for its white sandy beaches and beautiful architecture. This popular Craft Festival has garnered crowds of fine craft lovers... Read More » 


Saturday Siesta Key Rum Tours - start Oct 09 2021 0100PM

Saturday Siesta Key Rum Tours - Oct 09, 2021 01:00PM

Come see us in the Tasting Room about 10 minutes before the tour for some free samples! The tour is free and lasts about 45 to 60 minutes. The first 20 minutes or so will give you a short... Read More » 


Legends of Rock The Beatles and Roy Orbison Tribute - start Oct 10 2021 0700PM

Legends of Rock: The Beatles and Roy Orbison Tribute - Oct 10, 2021 07:00PM

In 1963 before the Beatles hit it big, the Beatles and Roy Orbison toured the country. And now, Sun Events is bringing you this monumental show LIVE for one night. Experience Roy Orbis... Read More » 


CannaFest Pre-Party - start Oct 16 2021 0600PM

CannaFest Pre-Party - Oct 16, 2021 06:00PM

Join us for a CannaFest pre-festival party! Oasis, in downtown Sarasota is the place to be on October 16th. This exclusive event will be limited to 200 tickets. Tickets are DONATION based... Read More » 


Fall Festival at University Town Center - start Oct 23 2021 1100AM

Fall Festival at University Town Center - start: Oct 23rd & 24th, 2021 11:00AM

Florida Penguin Productions & The Mall at University Town Center are bringing Sarasota a brand new Annual Fall Festival!Happening on October 23rd & 24th in the back parking lot of... Read More » 


Boeing Boeing - start Sep 29 2021 0200PM

Boeing Boeing - Through October 24th, 2021 02:00PM

In this 1960’s farce, self-styled Parisian lothario Bernard, who has Italian, German, and American fiancées, each a beautiful airline hostess with frequent “layovers.” He keeps “one up, o... Read More » 

Bingo Night Wednesday - start Jun 09 2021 0700PM

Bingo Night Wednesday - Through October 27th, 2021 07:00PM

Grab your friends and Join us for Spotlight Twisted Bingo every Wednesday Night at 7:00pm. Prizes and engaging hosts. Free to play. Progressive Jackpot - A mix of music and numbered bingo Read More » 


Stranger Things Multi Media  Laser Show Drive-In - start Oct 29 2021 0830PM

Stranger Things Multi Media & Laser Show Drive-In - Oct 29th, 2021 08:30PM

The Stranger Things Multi Media & Laser Show You know the Netflix story: After the mysterious and sudden vanishing of a young boy, the people of a small town begin to uncover secrets ... Read More » 


Broadway Cabaret Series - start Oct 14 2021 0300PM

Broadway Cabaret Series - Through October 31st, 2021 03:00PM

The triumphant series returns! Grammy and Emmy Award-winning performer John McDaniel will return as the Master of Ceremonies to host three fabulous performers straight from New York. Expe... Read More » 


Naples Fine Art Show - start Oct 30 2021 1000AM

Naples Fine Art Show™ - Through October 31st, 2021 10:00AM

Hot Works presents the 5rd Naples Fine Art Show, October 30 & October31, 2021 at the Naples Italian-American Club, located on a premium corner of Airport Pulling and Orange Blossom Ro... Read More »