| Jill French · REAL Broker · Sarasota & Bradenton |
Sep–Nov 2026 |
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🍂 🎃 🎨 🦞
Your Fall Sarasota Fun Guide
Fall on the Suncoast is absolutely magical 🌴
Cooler breezes, warm Gulf water, thinner crowds — and one of the most jam-packed event calendars of the year. September through November in Sarasota is truly a hidden gem. Here's everything you'll want to circle on the calendar! 🌺
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Hey friends! 👋 Jill here — and I have to say, fall might just be my favorite season in Sarasota. The humidity drops, the snowbirds start trickling back, and the event calendar absolutely explodes. From Oktoberfest on the bayfront to world-class sand sculpting on Siesta Key and a full-contact jousting fair in Myakka City (yes, really!), there is SO much ahead. Let's dive in! 🙌
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🌊 September — Season Warm-Up |
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SEP 19
FREE
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St. Armands Circle Art Festival 🎨
St. Armands Circle, Lido Key · Sep 19 · 10 a.m.–5 p.m. · Free Admission
The 4th Annual St. Armands Circle Art Festival kicks off fall in style! Browse fine art and handcrafted works from talented local and regional artists set against one of Sarasota's most iconic backdrops. Free to attend, easy to spend a gorgeous Saturday morning browsing and brunching around the circle. 🛍️
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SEP 26
⭐ PICK
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Sarasota Opera Food & Wine Festival 🍷
Sarasota Opera House · September 26 · An evening to savor
One of the most elegant evenings on the fall calendar. Exquisite food and wine pairings inside the gorgeous Sarasota Opera House — a true signature Sarasota experience. If you're a foodie, a wine lover, or just looking to kick off the season in style, this is THE event to mark. Tickets go fast! 🎶
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🎃 October — Festival Season Hits Full Swing |
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OCT 3
FREE
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Wellen Park Oktoberfest 🍺
Downtown Wellen Park · October 3
Kick off Oktoberfest season at Wellen Park's lakeside celebration — nearly 40 distinguished vintners, small bites from local restaurants, and live jazz at the amphitheater. One of the prettiest settings in the county for a fall evening. Prost! 🥨
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OCT 10
FREE
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ROCKtoberfest on the Bayfront 🎸
JD Hamel Park, Sarasota Bayfront · October 10 · 3 Days · FREE admission · Dog-friendly!
Three days of FREE live music, amazing food, local vendors, cold beer, and fall vibes right on Sarasota's beautiful bayfront. Bring the whole crew — this one is dog-friendly and family-friendly too. It's basically the unofficial kickoff of Sarasota's social season and one of the most fun weekends of the year. 🌊
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OCT 10–11
⭐ PICK
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Oktoberfest + The Benderson Chase Regatta 🚣
Nathan Benderson Park · Oct 10–11 · 10 a.m.–4 p.m. · Free admission / $20 parking
Oars AND pours — two great things happening at once at Nathan Benderson Park! Watch competitive rowing teams race on the lake while enjoying Oktoberfest food, music, dancing, and cold beer on shore. This is genuinely one of the most unique and fun event combos Sarasota does. Free admission, just pay for parking. Great for the whole family! 🏅
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OCT TBA
TICKETS
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Water Lantern Festival 🏮
Nathan Benderson Park · October (date TBA) · Tickets required
Thousands of glowing lanterns floating across the lake at Benderson Park — it's as magical as it sounds. This is one of Sarasota's most beautiful annual events and tickets always sell out. Watch the Visit Sarasota website for the exact date drop and grab yours early. A perfect date night or family memory in the making. ✨
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OCT 24
FREE
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Gulfcoast Pride Festival & Street Party 🌈
Rosemary District, Downtown Sarasota · Oct 24 · 4–11 p.m. · FREE
Sarasota's signature Pride celebration is back — an evening of live music, local art, food, and joyful community in the heart of downtown. Open to everyone: LGBTQ+ residents, families, allies, and neighbors. Free to attend, and genuinely one of the warmest community events of the year. 💛
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🍁 November — The Best of the Best |
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NOV 7– DEC 6
⭐ PICK
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Sarasota Medieval Fair ⚔️
Woods of Mallaranny, Myakka City · Sat & Sun, Nov 7–Dec 6 · 9:45 a.m.–5:30 p.m.
This one is seriously unlike anything else in the area — full-contact jousting, human combat chess matches, 14 stages of entertainment, rides, games, artisan shopping, and turkey legs the size of your forearm! 🍗 Running every Saturday and Sunday from November 7 through December 6 at the stunning 47-acre Woods of Mallaranny in Myakka City. Each weekend has its own unique theme. A total blast for the whole family — locals absolutely love this event! 🏰
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NOV 13–16
FREE
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Siesta Key Crystal Classic Sand Sculpting Festival 🏖️
Siesta Beach · November 13–16 · Free to attend
World-class professional sand sculptors from around the globe descend on the world's best white sand beach to create jaw-dropping, massive sculptures right before your eyes. There's also a speed-sculpting contest and an amateur competition. On the most beautiful beach in America. For free. It doesn't get more Sarasota than this. 🌟
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NOV 8–10
FREE
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Sarasota International Chalk Festival 🖌️
Historic Burns Square, Sarasota · November 8–10 · Free
The world's largest gathering of 3D illusion and pavement artists — over 150 artists from 30+ countries transforming Sarasota's streets into mind-bending masterpieces over three days. Plus live music, food trucks, and interactive areas for kids. New this year: stunning Flower Tapestry art installations. An absolute must-see. 🌸
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NOV 21
REGISTER
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Steps for Sarasota Walkathon & Community Celebration 👟
Junior League of Sarasota · Nathan Benderson Park · Nov 21 · 4 p.m. · Registration open!
The inaugural Steps for Sarasota Walkathon is a beautiful evening walk around Nathan Benderson Park followed by a festive celebration with food, entertainment, and community activities — all supporting the Junior League of Sarasota's mission. Perfect for families, friend groups, and local businesses who want to give back and have a wonderful time doing it. 💜
Registration is now open! Sign up at sarasota.jl.org — teams, sponsorships, and more details available there.
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📍 A Note From Jill
Fall is also when the Sarasota market really starts to move. Snowbirds return, second home buyers get serious, and smart sellers list before season peaks. Whether you're thinking about buying, selling, or just want to know what your home is worth heading into the new year — I'm always happy to have that conversation! 😊
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What's Your Home Worth? 🏡
No algorithms. No guesswork. Just real local expertise.
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Visit My Website |
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You're receiving this as a valued member of Jill's community. Event details are subject to change — always confirm with venues before attending. © 2026 Jill French, REAL Broker. To unsubscribe, reply with "unsubscribe" in the subject line.
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