October 2026 Things to Do in Southwest Florida

October is here, and while Southwest Florida may not have falling leaves and sweater weather quite yet, there are plenty of signs that fall has arrived!

From pumpkin festivals and Oktoberfest celebrations to outdoor concerts, farmers markets, Halloween events and family-friendly festivals, October is packed with things to do throughout Sarasota, Manatee and Charlotte Counties.

Whether you live here year-round, are returning for season, or are visiting Southwest Florida this fall, here are some events worth adding to your October calendar.

🎃 Fruitville Grove Pumpkin Festival

October 3–4, 10–11, 17–18, 24–25 & October 31–November 1
10:00 AM–5:00 PM
Fruitville Grove – Sarasota

It's hard to talk about fall in Sarasota without pumpkins!

The 38th Annual Pumpkin Festival at Fruitville Grove takes place every weekend throughout October. The festival includes a craft show, food trucks, live music, hayrides, a petting zoo, kids' activities, pumpkin painting, a butterfly garden, mini train rides, pony rides and plenty of pumpkins.

New attractions this year include a Mermaid Encounter on Saturdays, Kountry K-9 Dog Show, Bunny Village and Mini Donkey Mingle. There's even a walk-through haunted house for those looking for something a little spookier.

Admission is $5, children 6 and younger are free, and parking is free.

Fruitville Grove Pumpkin Festival details

🎶 Music on Main

October 2
6:00–9:00 PM
Lakewood Ranch Main Street

Start the month with live music and a night out at Lakewood Ranch Main Street.

Music on Main is a monthly community favorite featuring live music, food and plenty of activity along Main Street. It's an easy Friday night outing whether you're meeting friends, bringing the family or just looking for an excuse to get outside and enjoy the evening.

Lakewood Ranch Events Calendar

🎃 Hunsader Farms Pumpkin Festival

October 10–11, 17–18 & 24–25
9:00 AM–5:00 PM
Hunsader Farms – Bradenton

One of Manatee County's biggest fall traditions returns for its 35th year!

The Hunsader Farms Pumpkin Festival packs a LOT into a day: pumpkins, craft vendors, live music, hayrides, a corn maze, petting zoo, pioneer village, pony rides, pumpkin games, homemade ice cream, roasted corn and plenty of food.

And then things get a little less traditional. 😂

The 2026 entertainment lineup includes motorcycle stunt shows, BMX stunts, circus acts, a monster truck show, Wild West comedy stunt shows and even a pumpkin cannon that shoots pumpkins up to a half-mile.

Admission is $15 for ages 10+, $5 for children ages 5–9 and free for children under 5. Parking is $5. Admission and parking are cash only.

Hunsader Farms Pumpkin Festival

🍺 Oktoberfest Featuring the Benderson Chase

October 10–11
Nathan Benderson Park – Sarasota

Get ready for a weekend of Oktoberfest fun at Nathan Benderson Park.

The 2026 Oktoberfest Featuring the Benderson Chase is scheduled for October 10–11 and combines fall festival fun with activities at one of Sarasota's best-known outdoor recreation destinations.

Visit Sarasota County Events

🎨 Arts & Craft Fair in Punta Gorda

October 11
10:00 AM–3:00 PM
Punta Gorda

Spend a Sunday browsing local arts, crafts and unique finds in Punta Gorda. The city's October calendar includes an Arts & Craft Fair on October 11 from 10 AM to 3 PM.

It's a great excuse to make a day of it and enjoy downtown Punta Gorda and the waterfront while you're there.

Punta Gorda October Events Calendar

🎃 Punta Gorda Annual Fall Festival

October 17
12:00–4:00 PM
Laishley Park – Punta Gorda

The City of Punta Gorda and Punta Gorda Chamber of Commerce are teaming up for the Third Annual Neighborhood Fall Festival at Laishley Park.

This free, family-friendly event includes food, trick-or-treating, a costume contest, dessert walk, live entertainment and a new nonprofit expo featuring organizations from around the community.

Punta Gorda Fall Festival information

🌴 Alligator Creek Fest

October 17
South Venice Yacht Club – Venice

Here's one with a distinctly Florida twist on fall festival season.

The 7th Annual Alligator Creek Fest celebrates the local environment and the importance of protecting Alligator Creek, with a focus on water, wildlife and the area's way of life.

It's also a nice reminder that some of the best local events aren't just about entertainment—they're a chance to learn more about the natural areas that make Southwest Florida special.

🎵 Groovin' in the Gardens

October 18
Palma Sola Botanical Park – Bradenton

Spend a Sunday enjoying music surrounded by the tropical landscape of Palma Sola Botanical Park.

Groovin' in the Gardens returns October 18 with music from The Pops Orchestra Jazz Combo.

This is a great choice if your ideal October activity involves music and gardens rather than haunted houses and pumpkin cannons!

🛍️ Fall UTC Night Market

October 15
The Green at UTC – Sarasota

The Fall UTC Night Market gives you another reason to enjoy the cooler evening hours with shopping and a night out around University Town Center.

The event takes place October 15 at The Green at UTC.

🐾 Barks and Brews: Howl-o-ween

October 13
The Green at UTC – Sarasota

Even the dogs get an October event!

Barks and Brews: Howl-o-ween is scheduled for October 13 at The Green at UTC, making this one to check out for Southwest Florida's dog lovers.

👻 Spooktacular Fall Fest

October 24
10:00 AM–2:00 PM
Punta Gorda

Punta Gorda continues the Halloween fun with its Spooktacular Fall Fest on Saturday, October 24.

The event is included on the City of Punta Gorda's official October calendar and runs from 10 AM to 2 PM.

City of Punta Gorda Events Calendar

🎃 Trick or Treat on the Lake

October 27
Nathan Benderson Park – Sarasota

Halloween fun heads to Nathan Benderson Park with Trick or Treat on the Lake on October 27.

This is another fun option to add to the calendar for families looking for Halloween activities before the big night.

🍷 HalloWine Walk

October 28
5:00–7:30 PM
Lakewood Ranch

Here's one for the grown-ups.

Lakewood Ranch's HalloWine Walk takes place October 28 from 5:00 to 7:30 PM, adding a decidedly more adult option to the month's Halloween festivities.

Lakewood Ranch October Events

👻 BooFest on Main Street

October 30
6:00–9:00 PM
Lakewood Ranch Main Street

Halloween weekend kicks off at Lakewood Ranch with BooFest on Main Street on Friday, October 30.

The event runs from 6–9 PM and is one of several Halloween celebrations happening around the Sarasota-Manatee area that weekend.

🎃 Wellen Park Spooktacular

October 30
Downtown Wellen Park

Down in southern Sarasota County, Downtown Wellen is getting into the Halloween spirit too.

The Wellen Park Spooktacular is scheduled for October 30, giving North Port, Venice and Wellen Park area families another Halloween event close to home.

👻 Downtown Punta Gorda Halloween

October 31
Downtown Punta Gorda

And of course, we have to finish the month with Halloween!

Downtown Punta Gorda's Halloween celebration with the Punta Gorda Police Department is scheduled for October 31.

🌽 Don't Forget the Farmers Markets

October is also a great month to get back outside and explore some of Southwest Florida's local markets.

The Farmers' Market at Lakewood Ranch takes place Sundays from 10 AM–2 PM throughout October, while the Market at Nathan Benderson Park begins its season October 23 and continues on Fridays into the spring.

Markets like these are one of our favorite ways to support local growers, makers and small businesses while enjoying a beautiful Southwest Florida morning.

There's Plenty to Do This October in Southwest Florida

One of the best things about living in Southwest Florida is that there's almost always something happening somewhere nearby.

October brings a little bit of everything—pumpkin patches and fall festivals, live music, outdoor markets, community celebrations and plenty of Halloween fun. And unlike much of the country, we can enjoy most of it outdoors without worrying about digging the winter coats out of storage!

So grab your calendar, pick a few favorites and get out and enjoy October in Charlotte, Sarasota and Manatee Counties.

Which Southwest Florida event are you looking forward to this October?

Event dates, times, admission and activities may change. Be sure to check directly with event organizers before heading out.