🌴 Welcome to Your Sarasota Weekend
One of the things I love about living in Sarasota is how many different experiences we have within a relatively short drive.
This weekend is a perfect example.
You can spend Saturday enjoying live music and classic cars on Anna Maria Island, browse handmade art in downtown Sarasota, or head inland to Arcadia for something you might not expect to find in Florida—a genuine professional rodeo.
I’m not a farming, ranching or rodeo guy, but I can appreciate something that’s completely different from our usual beaches, restaurants and waterfront festivals. And Arcadia’s rodeo is the real deal.
Throw in pumpkin festivals, Halloween celebrations, a water lantern festival and a few longtime community traditions, and October is certainly keeping us busy.
Here’s what caught my attention this week.
⭐ Mike's Pick This Weekend
🌴 25th Annual Anna Maria Island Bay Fest
Saturday, October 17 | 10 AM–9 PM
Location: Pine Avenue, City of Anna Maria, Anna Maria Island
Admission: FREE
If you’re looking for a great reason to spend a day on Anna Maria Island, Bay Fest is a good one.
Celebrating its 25th anniversary, Bay Fest is the island’s largest and longest-running festival, bringing together live music, a classic car show, arts and crafts vendors, and plenty of food from local restaurants and vendors.
There will also be beer, wine, rum drinks, soda and water available for purchase.
It’s a family-friendly celebration that captures much of what makes Anna Maria Island special: a laid-back atmosphere, a welcoming community and a setting that’s hard to beat.
Why I picked it: I like events that feel connected to the community hosting them. Bay Fest has been an Anna Maria Island tradition for 25 years, and there’s something appealing about spending a Saturday strolling Pine Avenue, checking out classic cars and enjoying live music.
Mike’s Tip: Parking on Anna Maria Island can be challenging during major events. Consider arriving early, especially if you want to see the classic cars before the afternoon crowds.
⭐ Also Worth Your Weekend
🎤 Karaoke on The Green at UTC
Friday, October 16 | 7–10 PM
Location: The Green at UTC, near Rocco’s Tacos
Admission: FREE
Whether you’re ready to take the microphone or would rather cheer on someone else, Karaoke on The Green offers a relaxed Friday evening of music and fun.
It’s held every third Friday of the month, and there are plenty of nearby restaurants if you’d like to make an evening of it.
🤠 13th Annual Arcadia Fall PRCA Rodeo
Friday–Sunday, October 16–18
Location: Mosaic Arena, 2450 NE Roan Street, Arcadia
Tickets: $45–$75 | Parking $10
Here’s something that might surprise people who think Florida is all beaches and palm trees.
Arcadia has a longstanding rodeo tradition, and its annual Fall PRCA Rodeo brings professional cowboys and cowgirls to one of the area’s premier rodeo facilities.
Expect bull riding, bareback and saddle bronc riding, steer wrestling, team roping, barrel racing and more. There’s also Mutton Bustin’ and a Calf Scramble for the kids.
Saturday gates open at 3 PM; Sunday gates open at 11 AM. The event is scheduled rain or shine.
I’m not a rodeo person by background, but this is exactly the kind of experience I think makes exploring Florida interesting. Drive inland from Sarasota and you discover an entirely different side of our state.
🎶 53rd Annual Sun Fiesta — Venice
Friday–Sunday, October 16–18
Location: Centennial Park, 200 W. Venice Avenue, Downtown Venice
Admission: FREE
Venice celebrates its 53rd Annual Sun Fiesta with three days of live music, arts and crafts, food, entertainment and community traditions.
Among the festivities are the popular bed races, marching band performances, Miss Sun Fiesta, a dunk tank and auctions.
Festival Hours: Friday 3:45–9 PM, Saturday 9:25 AM–9:30 PM, and Sunday 9 AM–6 PM.
For anyone who enjoys the atmosphere of a traditional hometown festival, Sun Fiesta has plenty to offer.
🏮 Sarasota Water Lantern Festival
Saturday, October 17 | 4:30–8:30 PM
Location: Nathan Benderson Park, 5851 Nathan Benderson Circle, Sarasota
Tickets: Starting at $30.99
Imagine hundreds of softly glowing lanterns floating across the water as evening settles in.
The Sarasota Water Lantern Festival invites families and friends to decorate lanterns and take part in a coordinated launch after an afternoon of music, vendors, food trucks and activities.
Adult admission includes a floating lantern kit, LED candle, marker, drawstring bag and event access. Organizers also provide lantern retrieval and cleanup.
It’s a visually memorable way to spend a Saturday evening.
🎃 38th Annual Fruitville Grove Pumpkin Fest
Saturday & Sunday, October 17–18 | 10 AM–5 PM
Location: 7410 Fruitville Road, Sarasota
Admission & Parking: FREE
Fruitville Grove’s Pumpkin Fest continues with hayrides, pony rides, pumpkin painting, face painting, a petting zoo, mini train rides and plenty of fall decorations.
This year’s festival also features Hollowgraves Haunted Manor, a walk-through haunted house with live actors, recommended for ages 8 and older.
Free entertainment includes the Torres Family Circus and Extreme Riders shows at noon and 3 PM. A children’s costume contest takes place Saturday at 2 PM.
Some rides and activities cost $1–$10. Bring cash for vendors that don’t accept cards.
The festival continues October 24–25.
🎃 35th Annual Hunsader Farms Pumpkin Festival
Saturday & Sunday, October 17–18 | 9 AM–5 PM
Location: Hunsader Farms, County Road 675, East Manatee County
Admission: Adults $15 | Children 5–9 $5 | Under 5 FREE
Parking: $5 | Cash only
Another longstanding fall tradition, Hunsader Farms’ Pumpkin Festival offers an extensive lineup of activities for families.
You’ll find a craft show, live music, pioneer demonstrations, hayrides, pony rides, a petting zoo, frog-jumping championships, a children’s train ride, fresh roasted sweet corn, costume contests and much more.
It’s one of those events where families can easily spend several hours exploring.
The festival continues October 24–25.
🎨 St. Armands Fall Festival of the Arts
Saturday & Sunday, October 17–18 | 10 AM–5 PM
Location: St. Armands Circle Park, Sarasota
Admission: FREE
St. Armands Circle becomes an outdoor art gallery this weekend as artists from Florida and beyond display original work.
Expect paintings, sculpture, photography, jewelry, ceramics, glass, fiber art, woodworking and mixed-media creations.
The setting makes this an easy outing to combine with lunch, shopping or a walk around the Circle.
🎃 Boo! at The Bay
Saturday, October 17 | 4:30–7:45 PM
Location: Common Ground at The Bay, 1055 Boulevard of the Arts, Sarasota
Admission: FREE; tickets required
The Bay hosts its annual family-friendly Halloween celebration, complete with trick-or-treating, pumpkin decorating, yard games and a movie under the stars.
Kids can pick out a free pumpkin while supplies last, with 1,800 pumpkins available on a first-come, first-served basis.
The evening concludes with a sing-along screening of The Nightmare Before Christmas, beginning at 6:30 PM.
Costumes are encouraged, and food trucks will be on-site.
Event Details & Free Tickets
🌊 Sarasota Ski-A-Rees Water Ski Show
Sunday, October 18 | 2 PM
Location: Ski-A-Ree Stadium, 1602 Ken Thompson Parkway, Sarasota
Admission: FREE
The Sarasota Ski-A-Rees return with their Sunday afternoon water ski show.
It’s an entertaining local tradition featuring coordinated water skiing and impressive on-water skills, all with Sarasota Bay as the backdrop.
If you haven’t seen the Ski-A-Rees perform, it’s a fun way to spend a Sunday afternoon.
🎨 One More Worth Seeing
30th Annual Downtown Sarasota Craft Festival
Saturday & Sunday, October 17–18 | 10 AM–5 PM
Location: Main Street and Orange Avenue, Downtown Sarasota
Admission: FREE
Downtown Sarasota welcomes the 30th Annual Craft Festival, featuring a wide selection of handmade items from artists and craftspeople.
You’ll find jewelry, pottery, ceramics, photography, paintings, clothing and more.
The festival also includes an expansive Green Market with plants, orchids, exotic flowers, handmade soaps, gourmet spices and freshly popped kettle corn.
It’s a pleasant way to spend a couple of hours browsing downtown, and you might even find an early holiday gift or two.
☀️ Sarasota Anytime
Not everything worth doing around Sarasota comes with a special date on the calendar.
Try beach yoga on Siesta Key, spend Saturday morning wandering the Sarasota Farmers Market, catch one of our weekly drum circles or get out on the water.
These are the kinds of simple Sarasota experiences you can enjoy almost any week of the year.
If nothing on this weekend’s event calendar grabs you, try one of these instead:
🥁 Drum Circles
There are opportunities around the area to catch one of Sarasota’s casual sunset drum circles—an easy way to combine a beach evening with something uniquely local.
🧘 Yoga on the Beach
Trade the studio for the Gulf. Recurring beach-yoga sessions offer an entirely different way to start—or sometimes finish—the day.
🏃 Summer Beach Runs
Summer running programs turn an ordinary trip to the beach into an evening activity, with the Gulf providing a pretty good reward at the finish.
🎭 Local Performing Arts
Florida Studio Theatre and Sarasota’s other performing-arts organizations don’t simply disappear when season ends. Summer can be a great time to catch a performance without the winter-season rush.
🌴 UTC Fun
Night markets, movies, live music and other recurring programming make UTC one of the easiest places to check when you’re looking for something casual to do.
🌴 Local Weekend Favorite
A Different Side of Florida: Arcadia Fall Rodeo
We spend so much time talking about Sarasota’s beaches, waterfront and coastal lifestyle that it’s easy to overlook how quickly the scenery changes when you head inland.
Arcadia is a reminder that Florida has a deep agricultural and ranching heritage, too.
The rodeo is one reason to visit, but the area’s small-town atmosphere offers a completely different experience from Sarasota’s coastal communities.
You don’t have to be a cowboy—or even particularly interested in rodeos—to appreciate that contrast.
Sometimes discovering something new is as simple as driving in a different direction.
🌴 Before You Go...
Florida Has More Than One Personality
After living in Sarasota since 1988, I still enjoy discovering places and experiences that remind me how varied Florida really is.
Think about this weekend.
On Anna Maria Island, people will be listening to live music, admiring classic cars and enjoying a festival just a short walk from the Gulf.
In downtown Sarasota, artists will be displaying their work along Main Street.
And over in Arcadia, professional cowboys will be competing in bull riding and bronc riding in front of a completely different crowd.
Three experiences. Three very different sides of Florida. All within reach of Sarasota.
That’s something I appreciate about living here.
We may be best known for our beaches, but there’s a lot more to this part of Florida than sand and sunshine.
Whatever you decide to do this weekend, I hope you find something enjoyable.
Have a great weekend! 🙂
— Mike
SARASOTA WEEKLY
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📅 Upcoming Things to Do
A Few Sarasota Dates Worth Putting on Your Calendar
Some Sarasota events are worth knowing about more than a few days in advance. Here are a few coming up that have already landed on my calendar.
COMING SOON
Sarasota Fine Art Shows by Hot Works
October 31–November 1, 2026 | 10 a.m.–5 p.m.
J.D. Hamel Park | Downtown Sarasota | Free
Hot Works brings its juried fine art shows to Sarasota with professional artists selling original, personally handmade artwork across a variety of mediums and price ranges.
The first show of the season takes place at J.D. Hamel Park along the downtown bayfront, across from Marina Jack. Additional shows return to the bayfront in December and March, with a January weekend at St. Armands Circle.
Upcoming Dates
Oct. 31–Nov. 1 — J.D. Hamel Park, Downtown Sarasota
Dec. 19–20 — J.D. Hamel Park, Downtown Sarasota
Jan. 9–10, 2027 — St. Armands Circle
Mar. 6–7, 2027 — J.D. Hamel Park, Downtown Sarasota
🛍️ The Market at Nathan Benderson Park
Fridays, October 23, 2026–March 26, 2027 | 9 a.m.–1 p.m.
305 N. Cattlemen Road, Sarasota | Free
Start your Friday morning with The Market at Nathan Benderson Park, featuring local artists, boutique vendors, handmade goods and artisan foods.
The seasonal market takes place Fridays through March 26 in the field next to Homewood Suites in the UTC area, directly across from the Mote SEA parking area. Expect changing vendors, giveaways and other surprises throughout the season while supporting local small businesses.
🎨 18th Bi-Annual Le Marché Marketplace
Saturday, November 7 | 10 a.m.–4 p.m.
Five Points Park | Downtown Sarasota | Free
Downtown Sarasota gets a little Parisian flair when Le Marché Marketplace returns to Five Points Park.
The 18th edition of this outdoor market brings together a curated selection of local artists and makers offering original art, handcrafted goods, artisan products, specialty treats and unique gifts.
Because it’s right at Five Points in the heart of downtown, this is another event that lends itself to making a day of it—browse the market and then walk to one of downtown Sarasota’s restaurants or shops.
🍷 Forks & Corks Food and Wine Festival
January 23–24, 2027 | Sarasota
Celebrating its 20th year, Forks & Corks showcases locally owned independent restaurants from Sarasota and Manatee counties alongside winery owners and winemakers from around the world. The festival is Sarasota-Manatee Originals’ largest annual fundraiser.
Saturday, Jan. 23 — Forks & Corks University
10 a.m.–3 p.m. | Michael’s On East | $75–$100
Guided 90-minute Master Classes include 12 wine tastings and a pairing plate of light bites.
Sunday, Jan. 24 — Grand Tasting
11 a.m.–4 p.m. | The Ringling | $225–$550
More than 40 member restaurants and over 350 wines come together for the festival’s signature tasting event.
Tickets: VIP and Early Access go on sale November 3 at 9 a.m.; General Admission follows November 10 at 7 p.m.
🎄 A Country Christmas Jubilee
Saturday, December 5 • 10 AM–2 PM • EIO Rescue Ranch, Myakka City • Free
Spend a festive day on the ranch with 20+ local vendors, live acoustic Christmas music, adoptable dogs and puppies, rescue horses in the Christmas Barn, mini dog photo sessions, holiday photo ops, BBQ, coffee, sweet treats, raffles, and more. This family- and dog-friendly holiday market supports the work of EIO Rescue Ranch.
🖼️ Monumental Two-Day Fine Art, Sterling Silver, Americana & Antiques Auction
Upcoming Dates:
November 14-15, 2026
January 23–24, 2027
April 3–4, 2027
November 6–7, 2027
Time: 11 AM–7 PM each day
Location: Sarasota Estate Auction, 522 S. Pineapple Avenue, Sarasota
Admission: Free
Sarasota Estate Auction presents three upcoming two-day auction weekends featuring more than 2,000 lots of fine art, sterling silver, art glass, jewelry, antiques, Oriental rugs, sculptures, bronzes, Asian antiques, furniture and an extensive collection of porcelain.
Whether you’re a seasoned collector or simply enjoy discovering unusual and beautiful pieces, these auctions offer an opportunity to explore a wide variety of art, antiques and collectibles in downtown Sarasota.
Parking Tip: Limited parking is available alongside the building. Look for the large red Jorge Blanco sculpture.
Event Details & Auction Catalog
🔮 Spirit Fest Sarasota: Metaphysical, Holistic & Crystal Expo
December 5–6, 2026
Hours: Saturday 10 AM–6 PM | Sunday 10 AM–5:30 PM
Location: Sarasota County Fairgrounds & Robarts Arena, 3000 Ringling Boulevard, Sarasota
Admission: $12 per day or $18 for a weekend pass | Children 12 and under free
Parking: Free
Spirit Fest Sarasota returns with a two-day indoor expo featuring crystals, gemstones, jewelry, holistic wellness products and a variety of specialty vendors. Visitors can explore exhibits, meet practitioners and attend presentations covering topics such as meditation, energy healing, intuitive practices and personal wellness.
The event also features artists, handmade merchandise, books, natural skincare products and demonstrations. Guest speakers are included with admission, and food will be available for purchase.
📅 Hosting an Event in Sarasota?
Have a festival, concert, community event, performance or other local experience you’d like considered for an upcoming edition of Sarasota Weekly?
Send me the event name, date and time, location, short description, admission information, website or ticket link, and a high-quality photo.
Thank you,
-Mike Payne
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