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Bayfest on Anna Maria Island

Pine Avenue, Anna Maria Island, FL 34216 Pine Avenue, Anna Maria Island, FL

Get ready for a beloved island tradition! Bayfest is Anna Maria Island’s annual October street festival that celebrates the laid-back coastal lifestyle with live music, delicious food, refreshing drinks, and a lively classic car show. Stroll along Pine Avenue and browse unique arts and crafts vendors, enjoy family-friendly activities, and soak up the festive island atmosphere. This free event is a perfect way to kick off the fall season and experience the charm of Anna Maria Island like a local.

Sarasota Bay Water Lantern Festival

Nathan Benderson Park 5851 Nathan Benderson Circle, Sarasota, FL

Experience a magical evening of reflection and celebration at the Sarasota Bay Water Lantern Festival. Held along the serene waterfront, this family-friendly event invites guests to design and release personalized lanterns onto the water, creating a breathtaking display of glowing lights and heartfelt messages. Enjoy live music, food trucks, and a peaceful, welcoming atmosphere as the sun sets over Sarasota Bay. Each ticket includes a lantern kit, commemorative bag, and LED candle. Whether you're honoring a loved one, setting intentions, or simply enjoying the beauty of the moment, this unique event offers a memorable and meaningful experience for all ages.

Bradenton Zombie Pub Crawl

Dress like the undead and crawl through Bradenton’s best bars with drink specials.

Sarasota Oktoberfest

Raise your stein and celebrate Sarasota Oktoberfest, a lively three-day festival in downtown Sarasota blending authentic German traditions with Florida flair. Hosted by Paragon Festivals at scenic JD Hamel Park, this fall event features traditional German fare like bratwurst, schnitzel, and pretzels, alongside seasonal craft beers and festive drinks. Enjoy live music ranging from polka to rock, shop artisan vendors, and bring the whole family for a fun-filled weekend. Whether you're in it for the food, the music, or the gemütlichkeit, Sarasota Oktoberfest delivers a taste of Bavaria right on the Gulf Coast. Admission is free.

Selby Spooktacular

Family-friendly Halloween fun at Selby Gardens with trick-or-treating and spooky displays.

Trick or Treat at The Bay

Bring the kids in costume for trick-or-treating, games, and Halloween fun at The Bay park.

Selby Gardens Orchid Show: Fall Blooms

Immerse yourself in the stunning world of orchids during the Selby Gardens Orchid Show: Fall Blooms, hosted at the Downtown Sarasota campus of Marie Selby Botanical Gardens. This annual fall exhibition celebrates the beauty, diversity, and fragility of orchids through breathtaking horticultural displays, vibrant art installations, and interpretive exhibits exploring the science and history behind these exotic blooms.

Siesta Key Safe Treats

Enjoy safe and festive Halloween trick-or-treating along Siesta Key Village.

Sarasota Medieval Fair

Sarasota Medieval Fair

Step back in time and experience the magic of the Middle Ages at the Sarasota Medieval Fair, one of Florida’s most immersive and beloved annual festivals. This outdoor event brings history to life with thrilling jousting tournaments, live armored combat, themed entertainment, and a bustling marketplace filled with artisans, blacksmiths, glass blowers, and unique handmade goods.

Downtown Venice Fall Arts & Crafts Festival

Browse a charming collection of handmade arts and crafts in the heart of downtown Venice. This free festival is perfect for early holiday shopping and discovering local talent.

Fruitville Grove Pumpkin Festival (Final Weekend)

Celebrate the magic of fall at the 36th Annual Fruitville Grove Pumpkin Festival, a cherished family tradition in Sarasota! Held every weekend in October, this festive event transforms Fruitville Grove Farm into an autumn wonderland complete with pumpkins, live music, and seasonal fun for all ages.

Venice Main Street Fall Wine Walk

Sample wines while strolling through historic downtown Venice. Local shops stay open late and offer treats and specials during this evening of wine and community fun.