Things to Do: October 2023

There's no better way to experience Florida than in the Fall, and we’re here to tell you some of the awesome things you can enjoy on your stay this October. From live music to farmer’s markets, there’s something for everyone in the greater Siesta Key area. Check out the local offerings for this month!


Fruitville Grove Pumpkin Fest

Photo courtesy of Kids Out and About Tampa

The Fruitville Grove Pumpkin Fest is hosting its 35th year throughout the month of October. Enjoy fun for the whole family, including pony rides, face painting, a petting zoo, live music and more. Some activities are priced individually, but parking and admission are free. Even the kiddos can participate in a free costume contest every Saturday at 2pm, so be sure to arrive in style! The fest is a local staple, beloved by many residents of Fruitville. Check the event website for information on dates offered. 


Music on Main

Photo courtesy of Lakewood Ranch

Take a short trip to Lakewood Ranch the first Friday of every month for Music on Main! From 6-9pm, enjoy fun for the whole family, with live music, food, and drinks. Walk through dozens of food vendors and sponsor booths while the kids enjoy rides and other activities. Interested? Check out the event website here


Oktoberfest at Edelweiss

Photo courtesy of allevents

Do you enjoy a good lager? Look no further than the 11th annual Oktoberfest at Edelweiss in Bradenton! From October 11 - 15th, enjoy all things German and their festivities, which include yummy food, authentic entertainment, a fire spinner and more. Ring in the holiday with a keg tapping ceremony on October 11th at 5pm, or enjoy the other days of the festival with free admission. For location and event times each day, check out the website here


Falling For Vintage - Vintage Market

Photo courtesy of American Vintage Markets

Enjoy a twist on your typical flea market with a lineup of vendors specializing in vintage clothes, accessories, trinkets and more! This is the perfect stop to pick up something unique to remember your trip to Siesta Key. Expect to find not only clothes and accessories, but furniture, home decor, and collectables. Kids under 16 are free and otherwise admission is $8. The market is presented by American Vintage Markets, and will be held on October 13-14th from 9am - 4pm. For more information, refer to the event page here


Sarasota Water Lantern Festival

Photo courtesy of Water Lantern Festival 

The Sarasota Water Lantern Festival is a magical, once in a lifetime experience coming to the area on October 21st. Tickets come with live entertainment, your water lantern building kit, an LED candle, and a bag. The lanterns are also eco-friendly! Gates open at 4:30pm and the event ends around 8:30pm. Tickets are priced based on when you purchase, so be sure to buy them sooner rather than later! Visit the event website here to purchase tickets. 


20th Annual Boo Run 

Photo courtesy of Race Roster

If you’re looking for an active approach to your Halloween holiday, the Annual Boo Run is the perfect fit! This family-friendly 5K can be a walk or run and is offered in person or virtually. The race starts in the early morning, roughly around 8am. Enjoy sponsor tents and a costume contest, so be sure to come in your best. For more race information and to register, visit here

October is full of all things fun, frights, and Fall. Whichever way you decide to welcome in this season, we hope it’s with a stay at Tropical Beach. Take a sunset walk down our exclusive beach entrance with the cool Autumn breeze or listen to the waves crashing from your lounge chair. Tropical Beach is your ideal beach vacation spot!