| Jill French · REAL Broker · Sarasota & Bradenton |
Oct–Nov 2026 |
|
|
🍂 🎃 🎨 ⚔️
Your Fall Sarasota Fun Guide
Season is officially ON — and Sarasota is showing off! 🌴
October and November in Sarasota are genuinely magical — perfect weather, the snowbirds are back, and the event calendar is absolutely stacked. From bayfront festivals to world-class sand sculptures and a full-on medieval fair in the woods — here's your guide to the next two months! 🌺
|
|
Hey friends! 👋 Jill here — and I have to say, this might be the most packed fall season I've seen in years. There is something happening almost every single weekend, and several events this month are going to sell out or fill up fast. I've called out the ones you'll want to book in advance — keep an eye on those! Let's get into it. 🙌
|
|
🎟️ Book These Early — They Sell Out!
🎸 Boz Scaggs — Van Wezel · Oct 11
🎵 ABBA Tribute — Van Wezel · Oct 18
🏮 Water Lantern Festival — Benderson Park · Oct TBA |
🎤 David Foster & Katharine McPhee — Van Wezel · Nov 14
🏖️ Siesta Key Crystal Classic — Nov 13–16
👟 Steps for Sarasota — Register now! · Nov 21 |
|
|
| |
🎃 October — Festival Season in Full Swing |
|
|
OCT 3
FREE
|
Wellen Park Oktoberfest 🍺
Downtown Wellen Park · October 3
Kick off fall at Wellen Park's lakeside celebration — nearly 40 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! 🥨
|
|
|
|
OCT Sat &
Sun
⭐ PICK
|
Hunsader Farms Pumpkin Festival 🎃
5500 CR 675, Bradenton · Every Sat & Sun in October · 9 a.m.–5 p.m. · ~$15 adults / kids 10 & under free
Florida's largest family-friendly fall festival — and honestly one of the most fun things you can do in October on the Suncoast! Hayrides, live music, a corn maze, petting zoo, pony rides, juggling acts, stunt shows, a Pioneer Trades Village, Tiny Town for the little ones, and pumpkins of every size imaginable. Plus homemade ice cream, pumpkin pie, elephant ears, and roasted sweet corn. 🌽 This is a beloved annual tradition that locals and visitors have been coming to for 35 years. Confirm the exact October weekend dates at hunsaderfarms.com before you go — cash only at the gate! 🍂
|
|
|
|
OCT All
Month
FREE
|
The Bay's 4th Anniversary Celebration 🎉
The Bay Park · October 1–November 1 · 70+ free events all month
Sarasota's beloved bayfront park turns four this October and they are going BIG — 70+ free community events all month long, including Park-toberfest, Boo! at the Bay, and so much more. If you haven't explored The Bay yet, this is the perfect month to discover it. 🌊
|
|
|
|
OCT 11
🎟️ EARLY
|
Boz Scaggs Live at Van Wezel 🎸
Van Wezel Performing Arts Hall · October 11 · 7 p.m.
The rock and blues legend comes to Sarasota's iconic bayfront stage. Boz Scaggs is one of those rare artists where every song sounds exactly like you remembered — warm, soulful, and absolutely timeless. A fantastic evening out. Grab tickets soon — this one will fill up. 🎶
|
|
|
|
OCT 10–11
⭐ PICK
|
ROCKtoberfest + The Benderson Chase 🎸🚣
JD Hamel Bayfront + Nathan Benderson Park · Oct 10–11 · Mostly FREE
A two-for-one fall weekend! ROCKtoberfest brings three days of FREE live music, food, cold beer, and local vendors to the bayfront at JD Hamel Park — dog-friendly and family-friendly. Then head to Nathan Benderson Park for Oktoberfest + the Benderson Chase Regatta on October 10th: watch competitive rowing on the lake while enjoying fall food, dancing, and pints on shore. Two of the best events of the season on the same weekend! 🥨🌊
|
|
|
|
OCT 18
🎟️ EARLY
|
The Concert: A Tribute to ABBA 🪩
Van Wezel Performing Arts Hall · October 18
Dancing Queen, Mamma Mia, Fernando — all your favorites performed live on the Van Wezel stage. A joyful, high-energy night perfect for a girls' night out or date night. ABBA tribute shows are always a blast — and this crowd will absolutely be singing along. Get tickets before they go! 💛
|
|
|
|
OCT TBA
🎟️ EARLY
|
Water Lantern Festival 🏮
Nathan Benderson Park · October (exact date TBA) · Tickets required
Thousands of glowing lanterns floating across the lake at Benderson Park — pure magic. This is one of Sarasota's most beautiful annual events, and it sells out every single year. Watch for the date announcement and grab your tickets immediately. A perfect date night or family memory in the making. ✨
|
|
|
|
OCT 24
FREE
|
Gulfcoast Pride Festival & Street Party 🌈
Rosemary District, Downtown Sarasota · Oct 24 · 4–11 p.m. · FREE
Sarasota's signature Pride celebration returns — an evening of live music, art, food, and joyful community in the heart of downtown. Vendor marketplace 4–8 p.m., then street party through 11 p.m. Open to everyone and completely free. One of the warmest, most welcoming events of the year. 💛
|
|
|
| |
🍁 November — The Best of the Season |
|
|
NOV 8–15
⭐ PICK
|
Living Arts Festival — Bradenton · Sarasota · Venice 🎭
Venues across the Cultural Coast · November 8–15 · Mix of free and ticketed events
A full week-long celebration of everything that makes our Cultural Coast extraordinary — live theatre, dance, music, pop-up galleries, live murals, world premieres, and family events spanning venues from Bradenton to Venice. The Opening Night Gala is free! Some events do require tickets, so check the schedule at sarasotarising.org and plan your week. This is a real gem of our community. 🌟
|
|
|
|
NOV 8–10
FREE
|
Sarasota International Chalk Festival 🖌️
Historic Burns Square, Sarasota · Nov 8–10 · Free to attend
The world's largest 3D illusion and pavement art festival — 150+ artists from 30+ countries transforming downtown Sarasota's streets into jaw-dropping masterpieces over three days. Plus live music, food trucks, and kids' activities. New this year: stunning Flower Tapestry installations. Free to attend and absolutely mind-blowing. 🌸
|
|
|
|
NOV 13–16
FREE
|
Siesta Key Crystal Classic Sand Sculpting Festival 🏖️
Siesta Beach · November 13–16 · Free to attend
World-class professional sand sculptors from around the globe creating massive, breathtaking sculptures live on the world's best white sand beach. A speed-sculpting contest, amateur competition, and the most gorgeous backdrop imaginable — all for free. On Siesta Key. It just doesn't get more Sarasota than this. 🌟
|
|
|
|
NOV 14
🎟️ EARLY
|
David Foster & Katharine McPhee at Van Wezel 🎤
Van Wezel Performing Arts Hall · November 14 · 7 p.m.
One of the most anticipated shows of the fall season — legendary music producer David Foster and his powerhouse vocalist wife Katharine McPhee perform live on the bayfront stage. An absolutely stunning evening of music. This will sell out — don't wait on tickets. 🌹
|
|
|
|
NOV 7– DEC 6
TICKETS
|
Sarasota Medieval Fair ⚔️
Woods of Mallaranny, Myakka City · Sat & Sun, Nov 7–Dec 6 · 9:45 a.m.–5:30 p.m.
Full-contact jousting. Human combat chess. 14 stages. 140+ artisan shops. 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. An absolute blast for the whole family and one of the most unique events in all of Florida. 🏰
|
|
|
|
NOV 21
REGISTER
|
Steps for Sarasota Walkathon & Community Celebration 👟
Junior League of Sarasota · Nathan Benderson Park · Nov 21 · 4 p.m.
The inaugural Steps for Sarasota Walkathon is a beautiful evening walk around Nathan Benderson Park followed by a festive community celebration — food, entertainment, and fun supporting the Junior League of Sarasota's mission. A wonderful way to give back while having a great time with friends and family. 💜
Registration is open now! Sign up at sarasota.jl.org
|
|
|
|
📍 A Note From Jill
Fall is when the Sarasota market really heats up — 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 chat! 😊
|
|
|
What's Your Home Worth? 🏡
No algorithms. No guesswork. Just real local expertise.
|
Visit My Website |
|
|
|
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.
|
