Coming This Week
Nothing Until Wednesday, Then All of It on Saturday
Salsa at The Bay on Wednesday. Then Saturday tries to fit a pumpkin farm, a beach 5K, a toddler world championship, a wine flight, an Oktoberfest and a ROCKtoberfest into one day. Boz Scaggs takes Sunday.
I went through the calendars for both counties this morning, and the week has a shape. Monday: nothing. Tuesday: nothing. Wednesday: one dance party. Then Saturday shows up with everything at once, like it packed for a cruise the night before and just threw it all in one bag.
Eight things, all checked against the organizer's own page. Six of them are on Saturday. I didn't plan it that way. Saturday did.
01 · Salsa & Sunsets at The Bay
Wed., Oct. 7 · The Nest at The Bay Park, 1055 Blvd of the Arts, Sarasota
Time: 6:30–8:30 p.m. · Price: Free
The Bay kicks off its fourth-anniversary month with a champagne toast, then a Latin dance party with live music by Bri Rivera & Friends. Beer and wine sales that night go to the park. Bad weather cancels it, so check before you leave.
A park turning four gets a champagne toast and a live band. I turned four and got a juice box and a nap. The Bay is doing better than I did.
02 · Hunsader Farms Pumpkin Festival
Sat.–Sun., Oct. 10–11 (also Oct. 17–18 and 24–25) · Hunsader Farms, 5500 C.R. 675, Bradenton
Time: 9 a.m.–5 p.m. · Price: $15 ages 10 and up, $5 ages 5–9, free under 5, $5 parking. Cash only.
Opening weekend. Hayrides, a corn maze, pony rides, a petting zoo, a craft show, live music and farm-roasted sweet corn.
It's cash only, which makes it the most authentic farm experience on the property. Hit the ATM before the hayride, not after.
03 · AME Dolphin Dash 5K and Fin's Fun Run
Sat., Oct. 10 · Coquina Beach, 2650 Gulf Drive (pavilion by the playground), Bradenton Beach
Time: Starts 9 a.m.; fun run 9:15, 5K 9:30 · Price: Fun run $15, 5K $35 (online sign-up until 8:45 a.m. race day)
A beach 5K and a roughly 1K untimed fun run, with every dollar going to Anna Maria Elementary. You don't need to be an AME family to sign up.
The race FAQ asks itself, "Is this a pop up event or legit?" and answers, "super legit. Like County permits and beach patrol involved legit." I have never trusted a 5K more. The same FAQ says you can walk, skip or dance the course, which is the most Anna Maria Island race rule ever written.
04 · Strider Cup World Championship
Sat., Oct. 10 · Sarasota BMX, 1590 N. Tuttle Ave., Sarasota
Time: Races start 9 a.m. (packet pickup 7–9 a.m.) · Price: Racer sign-up closes Oct. 8; spectators see link. Free parking.
A balance-bike world championship for kids ages 2 to 5. Strider held its first one in Sarasota 15 years ago and brought the anniversary race back here. Genuine Strider bikes only, no other brands.
Two-year-olds racing for a world title on a track that also hosts Olympic qualifiers. The organizers encourage pompoms and cowbells. Bring both. These people are working harder than you this weekend.
05 · The Tasting Room at Sarasota Wine Co. (Kevin Keys pick)
Sat., Oct. 10 · Sarasota Wine Co., 64 S. Palm Ave., Sarasota
Time: 1–3 p.m. · Price: $35 plus $2.45 tax and a $0.94 ticket fee
A ticketed flight of four wines with a new theme each week, plus an ounce of wine chips and printed tasting notes. Kevin already wrote this one up and has not stopped talking about the chips.
Kevin Keys pick. He asked me to say it's "a very thoughtful flight." He has not seen the theme yet.
06 · Sarasota Oktoberfest featuring the Benderson Chase Regatta
Sat.–Sun., Oct. 10–11 · Nathan Benderson Park, 5851 Nathan Benderson Circle, Sarasota
Time: 10 a.m.–5 p.m. · Price: Free admission; parking $20 per car
Youth rowing, masters and adult dragon boat races on the lake. German food, live German bands, a beer garden, a DJ, a kids zone and stein hoisting on land.
Some people race boats across a lake. Other people hold a full stein straight out for as long as they can. At Benderson Park, both count as competition.
07 · ROCKtoberfest
Sat., Oct. 10 · J.D. Hamel Park, 199 Bayfront Drive (across from the Sarasota Bayfront Marina), Sarasota
Time: 5–11 p.m. · Price: Free admission; no ticket system for food or drinks
Free live music on the bayfront, food, drinks and local vendors, put on by the Sarasota Downtown Merchants as a fundraiser for downtown. Dogs and kids welcome.
Yes, Saturday has an Oktoberfest at 10 a.m. and a ROCKtoberfest at 5 p.m. My only advice is pace yourself. That's the whole advice.
08 · Boz Scaggs Rhythm Review 2026
Sun., Oct. 11 · Van Wezel Performing Arts Hall, 777 N. Tamiami Trail, Sarasota
Time: 7 p.m. (doors one hour before) · Price: $61–$253, fees included
The Silk Degrees guy, on the bay, on a Sunday night.
The man who recorded "Lido Shuffle" is playing a short drive from Lido. If he skips it, Sarasota will clap politely and bring it up at brunch until Thanksgiving.
Sandy's sign-off
Pick two Saturday things. Three if you're under five and on a balance bike. Monday and Tuesday are free if you need to rest up for it.
— Sandy
Times and details can change, check the organizer's page.
