Sarasota Weekend Events: October 24–25, 2026
Darren Dowling
Darren Dowling
Looking for exciting things to do in Sarasota this weekend? October 24–25, 2026, brings a mix of fall festivities, creative experiences, live entertainment, local food, and family-friendly activities throughout Sarasota and the surrounding area.
Whether you're planning a day out with family, searching for unique shopping finds, enjoying the local arts scene, or looking for an entertaining night out, there's something to add to your weekend calendar.
Here are eight Sarasota-area events to explore this weekend.
Dates: Saturday and Sunday, October 24–25, 2026
Time: 10 AM–5 PM
Location: Fruitville Grove, 7410 Fruitville Road, Sarasota
Admission: $5; children 6 and under enter free. Parking is free.
Nothing says fall quite like a pumpkin festival, and Fruitville Grove's annual celebration offers plenty of seasonal fun.
Visitors can browse pumpkins and fall decorations, explore local craft vendors, enjoy food trucks, and participate in family-friendly activities. Festival attractions include hayrides, pony rides, a petting zoo, pumpkin painting, a mini train, a children's play area, and live entertainment.
The festival also features a haunted attraction for visitors looking for a Halloween-season thrill. Families with young children can enjoy the farm atmosphere while making the most of the autumn festivities.
With activities throughout the day, it's a great option for families looking to spend a few hours outdoors.
More information: Fruitville Grove Pumpkin Festival
Date: Saturday, October 24, 2026
Time: 4–11 PM
Location: Pride Plaza and the Rosemary District, Sarasota
Admission: Free
Sarasota's Gulfcoast Pride Festival brings the community together for an evening celebrating inclusion, creativity, and connection.
The all-ages community festival features live entertainment, local vendors, community organizations, food for purchase, and a dedicated kids' zone. The festival portion is scheduled through 8 PM, followed by a DJ-led street party that continues into the evening.
Whether you're attending with friends, enjoying the entertainment, or exploring local vendors, the event offers an opportunity to experience Sarasota's diverse community and lively downtown atmosphere.
More information: Visit Sarasota County – Events and Festivals
Dates: Saturday and Sunday, October 24–25, 2026
Time: 10 AM–5 PM
Location: St. Armands Circle Park, Sarasota
Admission: Free
Art lovers and shoppers can spend the weekend exploring the St. Armands Circle Fall Art & Craft Show.
The outdoor event features artwork, handmade crafts, seasonal decorations, and distinctive items from participating artists and vendors. It's a good opportunity to discover one-of-a-kind pieces while supporting creative businesses.
After browsing the booths, visitors can stroll around St. Armands Circle, known for its boutiques, restaurants, and walkable shopping district.
If you're looking for a relaxed weekend activity that combines shopping, art, and dining, this event is worth adding to your plans.
More information: City of Sarasota – Fall Art & Craft Show
Date: Saturday, October 24, 2026
Time: 7:30 PM
Location: Van Wezel Performing Arts Hall, 777 North Tamiami Trail, Sarasota
Movie fans and music lovers can experience Star Wars: Return of the Jedi in a spectacular concert setting.
Sarasota Orchestra performs John Williams' memorable score live while the film plays on a large screen. The combination of a beloved cinematic classic and a live symphony offers a different way to experience the story, music, and action.
This event is an appealing choice for couples, families with older children, and anyone who appreciates film music or orchestral performances.
Tickets are required, and availability and prices may vary. Check the official event page before making plans.
More information: Sarasota Orchestra – Star Wars: Return of the Jedi
Date: Saturday, October 24, 2026
Time: 5–8 PM
Location: Art Center Sarasota, 707 North Tamiami Trail, Sarasota
Admission: $15 for members and $20 for nonmembers
Art takes center stage at Art Royale, a live painting competition where local artists race against the clock to create original works inspired by surprise themes and creative challenges.
The event features 10 artists competing for one championship. Guests can watch the creative process unfold, enjoy music and refreshments, vote for their favorite work, and explore opportunities to purchase artwork.
Unlike a traditional gallery visit, Art Royale lets visitors see the artistic process in real time. It's an engaging experience for anyone interested in visual arts, local talent, or creative entertainment.
More information: Art Center Sarasota – Upcoming Events
Date: Saturday, October 24, 2026
Time: 9 AM–4 PM
Location: Robarts Arena, Sarasota Fairgrounds, 3000 Ringling Boulevard, Sarasota
If you enjoy finding unusual treasures, American Vintage Markets offers a chance to browse vintage décor, antiques, collectibles, handmade goods, jewelry, and repurposed pieces.
The indoor market brings together vendors, makers, and collectors, making it a worthwhile stop for shoppers searching for distinctive home accents, gifts, or items with character.
Admission is listed at $8 per person for groups of two or more, or $10 for a two-day pass. Children under 16 enter free, and parking is free. Check the organizer's website for current admission details.
More information: American Vintage Markets – Sarasota
Date: Sunday, October 25, 2026
Time: Noon–3 PM
Location: The Oval parking area at The Bay Park, 1055 Boulevard of the Arts, Sarasota
Admission: Free; food purchases are extra.
Spend Sunday afternoon enjoying local flavors at Taste of The Bay, a food festival celebrating independent restaurants in the Sarasota-Manatee region.
Presented in partnership with Sarasota-Manatee Originals, the event features signature dishes from participating local restaurants, giving visitors an opportunity to sample different flavors in one waterfront setting.
Live music from Kettle of Fish adds to the atmosphere, while The Bay Park provides a scenic place to gather with friends and family.
Admission is free, and food tickets are sold in $5 increments. Most dishes are listed at three to five tickets. Registration is encouraged, so check the official event page before attending.
More information: The Bay Sarasota – Taste of The Bay
Date: Sunday, October 25, 2026
Time: 6 PM
Location: Van Wezel Performing Arts Hall, 777 North Tamiami Trail, Sarasota
Tickets: Listed at $41–$81
For a Halloween-season experience with a dramatic twist, The Vampire Circus brings a dark, theatrical spectacle to Sarasota.
The production blends circus acrobatics, dance, comedy, illusion, and cabaret-inspired entertainment in a gothic setting. With international performers and a mysterious storyline, the show offers something different from a traditional concert or stage performance.
It's a compelling option for adults, couples, and older audiences looking for an unusual evening of live entertainment.
Tickets are required. Review the venue's official listing for current pricing, availability, and any age guidance before booking.
More information: Van Wezel Performing Arts Hall – The Vampire Circus
From the seasonal atmosphere at Fruitville Grove to the creativity of Art Royale, the food at Taste of The Bay, and the live performances at Van Wezel, the weekend of October 24–25 offers a variety of ways to enjoy the Sarasota region.
Here are a few ideas to help you plan:
Check official event pages for updated schedules, ticket availability, parking details, and any last-minute changes before heading out.
One of the benefits of living in the Sarasota area is having access to a wide range of cultural events, outdoor activities, local dining, and community gatherings throughout the year.
Whether you're drawn to Sarasota's arts and waterfront lifestyle or the neighborhoods and amenities of Lakewood Ranch, choosing the right home also means finding a community that fits your everyday life.
Beyond Realty
2170 Main Street, Suite 103, Sarasota, FL 34237
941-204-0493
Darren Dowling is a Sarasota-based real estate broker-owner specializing in Sarasota and Lakewood Ranch residential real estate, new construction, and relocation.
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