Sarasota Weekend Highlights: Art, Music, Pumpkins & Dragon Boat Championships (Oct 17–19, 2025)
Darren Dowling
Darren Dowling
Fall in Sarasota and Bradenton is in full swing, and this weekend is packed with exciting events for families, art lovers, and outdoor enthusiasts. From live music downtown to high-energy dragon boat racing, plus seasonal pumpkin fun, there’s no shortage of ways to enjoy the Gulf Coast.
When: Oct 17–19 | Fri 4 PM–10 PM | Sat 10 AM–10 PM | Sun 10 AM–6 PM
Where: JD Hamel Park, Downtown Sarasota
Details: This three-day festival brings live music, food vendors, craft beer, and family-friendly fun to the heart of downtown Sarasota. Enjoy local shops, art booths, and a vibrant community atmosphere.
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When: Oct 18–19 | 10 AM–5 PM
Where: 1 Central Avenue / 5 Points Park, Sarasota
Details: Browse handcrafted art, pottery, jewelry, and photography created by talented local and national artisans. A perfect event for creative minds and collectors alike.
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When: Oct 18–19 | 10 AM–5 PM
Where: St. Armands Circle Park, Sarasota
Details: Discover fine art from painters, sculptors, and glass artists in an outdoor festival setting. Meet the artists, explore unique pieces, and take home a beautiful memory.
Event info
When: Oct 16–19, 2025
Where: Nathan Benderson Park, Sarasota
Details: Experience high-energy dragon boat racing as teams from across the nation compete at Sarasota’s premier park. A thrilling weekend for sports fans and families alike.
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When: Oct 18–19 | 9 AM–5 PM
Where: 5500 C.R. 675, Bradenton, FL
Details: Celebrate fall with pumpkin picking, hayrides, a petting zoo, live music, craft booths, and delicious seasonal treats. A family favorite in Manatee County for decades!
Festival info
| Date | Time | Event | Location |
|---|---|---|---|
| Oct 17 | 4 PM–10 PM | ROCKtoberfest | JD Hamel Park |
| Oct 18 | 10 AM–10 PM | ROCKtoberfest | JD Hamel Park |
| Oct 18 | 10 AM–5 PM | Craft Festival | 1 Central Ave / 5 Points Park |
| Oct 18 | 10 AM–5 PM | St. Armands Fine Art Festival | St. Armands Circle |
| Oct 18 | 9 AM–5 PM | Pumpkin Festival | Hunsader Farms, Bradenton |
| Oct 19 | 10 AM–6 PM | ROCKtoberfest | JD Hamel Park |
| Oct 19 | 10 AM–5 PM | Craft Festival | 1 Central Ave / 5 Points Park |
| Oct 19 | 10 AM–5 PM | St. Armands Fine Art Festival | St. Armands Circle |
Fall in Sarasota & Bradenton is the perfect time to explore local art, enjoy live music, and celebrate seasonal traditions with friends and family.
🏡 Thinking of calling Sarasota or Lakewood Ranch home?
Connect with Darren Dowling of Beyond Realty — your trusted local Realtor with expert knowledge of the community and the best properties available.
📞 Call/Text: (941) 204-0493
Experience the best of Sarasota & Manatee this weekend — live music, art, pumpkins, and high-energy dragon boat races!
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