THIS MONTH IN SARASOTA

October 2026

Fall has arrived in Sarasota — and October is one of the best months to experience the area like a local.

From art and live music to outdoor markets, family activities, workshops, food experiences and plenty of Halloween fun, there is something happening throughout Sarasota and the surrounding communities.

Here are some of the things worth putting on your October calendar.

🍂 OCTOBER HIGHLIGHTS

🌿 OCTOBER 3–10

FALL FESTIVALS, ART & FAMILY FUN

🎨 WHY AI? The Digital Paintings of Elisabeth Trostli

Oct. 3–31 | Arts Advocates Gallery

A thought-provoking exhibition exploring the relationship between artificial intelligence, imagination and the creative process. Open Saturdays in October, 2–4 PM, and free to attend.

🎭 The Beatle Girls

Oct. 3–11 | Tree Fort Productions

A musical theater experience celebrating the music and spirit of The Beatles.

🎃 Fruitville Grove Pumpkin Festival

Throughout October | Fruitville Grove

Pumpkins, farm activities and classic fall fun for families.

🌴 One Park FOUR All Anniversary Celebration

Oct. 3–Nov. 1 | The Bay

A month-long celebration of The Bay's fourth anniversary.

⚽ Sarasota Paradise vs. Charlotte Independence

Oct. 3 | Premier Sports Campus at Lakewood Ranch

🧘 Free Fit Day

Oct. 4 | Jefferson Fit, Downtown Sarasota

A recurring community wellness event.

🛍️ Farmers' Market at Lakewood Ranch

Sundays through Dec. 28 | Waterside Place

A relaxed Sunday tradition with local vendors, food and the Waterside setting.

💃 Salsa & Sunsets — 4th Anniversary Celebration

Oct. 7 | The Bay

Champagne, live music and a Latino-inspired dance party overlooking Sarasota Bay.

🎨 Meet the Muralist: Trinity Rivard

Oct. 6 | Gillespie Park

Meet Tampa-based mural artist Trinity Rivard, learn about his creative process and even participate in painting the “Above the Nest” mural.

🚲 Strider Cup World Championship

Oct. 9–11 | Sarasota BMX

A fun event to watch with younger kids and cycling fans.

🎶 Legacy: Motown & More!

Oct. 3–4 | Florida Studio Theatre

🎭 PinocchioThrough

Oct. 18 | Florida Studio Theatre

A family-friendly theatrical option during the first half of the month.

🌿 OCTOBER 10–18

ART, MUSIC, MARKETS & COMMUNITY

🚗 Sarasota Cars & Coffee

Oct. 10 | The Mall at UTC

A Saturday morning gathering for classic and contemporary car enthusiasts.

🌱 UF/IFAS Master Gardener Annual Plant Sale & EdFest

Oct. 10 | UF/IFAS Extension Sarasota County

A great stop for gardeners, plant lovers and anyone looking to bring a little more Florida into their yard.

🎨 Diverse Fest

Oct. 10 | Harvest House

Live music, dance, theater, family activities and community programming.

🍺 Oktoberfest Featuring the Benderson Chase

Oct. 10–11 | Nathan Benderson Park

🎨 Art & Soul Bazaar

Oct. 10 | The Art Advocate

Local art, makers and creative finds.

🎶 Don Soledad Trio: Art & Passion

Oct. 10 | WSLR+Fogartyville

🎼 A Mass for Peace

Oct. 10 | First United Methodist Church

🛍️ The Local Collective Indoor Market

Oct. 11 | Sarasota

A curated indoor market featuring local vendors.

🐕 Barks & Brews: Howl-o-ween

Oct. 13 | The Green at UTC

A Halloween-themed event for dogs and their humans.

🍷 October 4-Course French Wine Dinner

Oct. 13 | Figaro Bistro & Wine Bar

A good option for a more grown-up evening.

🎻 Sarasota Orchestra: Planes, Trains & Automobiles

Oct. 14–17 | Sarasota Orchestra

A full orchestral program for a classic Sarasota cultural evening.

🎬 The Lost Leonardo

Oct. 14 | Burns Court Cinema

Part of the Art Film Series.

🎭 Sophisticated Ladies

Oct. 14–Nov. 22 | Westcoast Black Theatre Troupe

A musical tribute to the music of Duke Ellington.

🌙 Fall UTC Night Market

Oct. 15 | The Green at UTC

An evening market with shopping, food and community atmosphere.

🎶 Ella and The Bossa Beat

Oct. 15 | WSLR+Fogartyville

🌿 Hermitage Sunsets @ Selby Gardens: New Music Under the Old Oak

Oct. 16 | Marie Selby Botanical Gardens

Music, nature and an especially beautiful Sarasota setting.

✨ Night of Wonder: Season Kickoff Party

Oct. 16 | The Ringling

An evening celebrating the start of the season at one of Sarasota's signature cultural institutions.

🐎 $7,500 Halloween High Jump

Oct. 16 | Fox Lea Farm

🍽️ Autumn Harvest Dinner

Oct. 16 | All Faiths Food Bank

🎬 Dracula — Wine Tasting & Film Night

Oct. 16 | Tree Fort Productions

🎨 OCTOBER 17–25

A VERY SARASOTA WEEKEND

🌿 Alligator Creek Fest

Oct. 17 | South Venice Yacht Club

A community celebration focused on water, wildlife and protecting Alligator Creek.

🐾 Paws for the CureOct. 17 | Dog Bar Sarasota

A pet-friendly fundraiser.

🎨 St. Armands Fall Festival of the Arts

Oct. 17–18 | St. Armands Circle

Browse artwork from artists and makers while enjoying one of Sarasota's most recognizable shopping and dining districts.

🎶 Groovin' in the Gardens

Oct. 18 | Palma Sola Botanical Park

Live music in a beautiful garden setting.

🎭 Behind the Curtain: Exploring the Van WezelBeginning

Oct. 19

A behind-the-scenes look at the art, architecture and performance spaces of the Van Wezel.

🎨 Echoes of Sarasota — Free Art Tours

Oct. 20 | Van Wezel Performing Arts Hall

Free docent-led tours exploring Sarasota's history through the art displayed throughout the building.

🍷 Chilean Wine Dinner with Viña Concha y Toro

Oct. 22 | Tripletail Seafood & Spirits

🎤 AL Ernest & The Jester Dogs

Oct. 22 | WSLR+Fogartyville

🛍️ American Vintage Markets

Oct. 23–24 | Robarts Arena

A treasure-hunting stop for vintage finds, collectibles and unique pieces.

🛍️ Market at Nathan Benderson Park

Fridays beginning Oct. 23

A new recurring market running through March 2027.

⭐ OCTOBER 23–25

ONE OF THE BUSIEST WEEKENDS OF THE MONTH

🎬 Movies Under the Stars: Hocus Pocus

Oct. 23 | The Green at UTC

🎻 Sarasota Orchestra: Star Wars — Return of the Jedi

Oct. 23–24 | Van Wezel Performing Arts Hall

🌿 Public Grand Opening: Southeast Quad at the Celery Fields

Oct. 24 | Celery Fields

A new outdoor destination adjacent to the Celery Fields, with the grand opening offering a chance to explore the new space.

🎨 Creative Liberties Family Art Day

Oct. 24 | Creative Liberties Creative Academy

🐹 Capybara Halloween: Capy Boo-Ra Bash

Oct. 24 | Happy Capys

A very Sarasota-style Halloween activity for families.

🎶 Humanity Day

Oct. 24 | WSLR+Fogartyville

🏳️‍🌈 Gulfcoast Pride Festival & Street Party

Oct. 24 | Rosemary District

A community celebration with the festival and street-party atmosphere.

🎻 Candlelight Concerts

Oct. 24 | St. Boniface Episcopal Church

Choose from Halloween classics, Hans Zimmer or Fleetwood Mac tribute programs.

⚽ Sarasota Paradise vs. Westchester SC

Oct. 24 | Premier Sports Campus at Lakewood Ranch

🎃 OCTOBER 27–31

HALLOWEEN WEEKEND

🎃 Trick or Treat on the Lake

Oct. 27 | Nathan Benderson Park

A family-friendly Halloween evening.

🎻 Sarasota Orchestra: Adagio for Strings

Oct. 29 | Sarasota Orchestra

👻 Wellen Park Spooktacular

Oct. 30 | Downtown Wellen Park

🎃 BooFest at Lakewood Ranch Main Street

Oct. 30 | Lakewood Ranch

🎭 Hansel and Gretel

Oct. 30–Nov. 14 | Sarasota Opera

🎶 Hocus Pocus Pops II

Oct. 30 | Riverview Performing Arts Center

🎭 Freaky Friday

Oct. 30–Nov. 22 | Venice Theatre

🏃‍♀️ Runaway Pumpkin 5K & Family Fest

Oct. 31 | Child Protection Center

🎭 We're Doomed!

Oct. 31 | Florida Studio Theatre

🚴 2026 UCI BMX Racing World Cup

Oct. 31–Nov. 1 | Sarasota BMX

🎃 Halloween Havoc

\]Oct. 31–Nov. 1 | Youth Athletic Complex

🎨 DON'T MISS THE EXHIBITIONS

If you're looking for something a little quieter than a festival, October is a great month to explore Sarasota's art scene.

WHY AI?

Arts Advocates Gallery | Through Oct. 31

A fascinating exhibition exploring AI, creativity and the future of digital art. Free admission.

THE RINGLING

Make time for the Museum of At, Circus Museum, Ca' d'Zan and Bayfront Gardens.

The Ringling campus combines art, history, architecture and gardens into one of Sarasota's most distinctive cultural experiences. The John and Mable Ringling Museum of Art

SELBY GARDENS

Pair an exhibition or event with a walk through the gardens and the bayfront setting.

Marie Selby Botanical Gardens Downtown Sarasota

SARASOTA ART MUSEUM

For contemporary art lovers, make time for the exhibitions at:

Sarasota Art Museum

ART CENTER SARASOTA

A good stop for discovering local and regional artists—and for checking out current classes and creative programs.

Art Center Sarasota

🌱 FOR THE GARDEN LOVERS

October 10

UF/IFAS Master Gardener Plant Sale & EdFest

October 18

Groovin' in the Gardens

Throughout the month

Explore the gardens at Selby Gardens, The Ringling and Historic Spanish Point.

🛍️ MARKET DAYS

Looking for a slower Sarasota morning?

Sarasota Farmers' Market

Saturdays from 7:00 AM to 1:00 PM • Lemon Ave & Main Street, Downtown Sarasota

Lakewood Ranch Farmers' Market

Sundays from 10:00 AM to 2:00 PM • 1561 Lakefront Dr, Lakewood Ranch, FL 34240

The Local Collective Indoor Market

Oct. 11 from 12:00 PM to 4:00 PM • Aleur, Sarasota, Florida

Fall UTC Night Market

Oct. 15 from 6:30 PM to 9:30 PM  • The Green at UTC 125 N Cattlemen Road, Sarasota FL

American Vintage Markets

Oct. 23–24 from 9:00 AM to 4:00 PM • Indoors at Robarts Arena, Sarasota Fairgrounds, 3000 Ringling Blvd, Sarasota FL

Market at Nathan Benderson Park

Fridays beginning Oct. 23 from 9:00 AM to 1:00 PM • Adjacent to the playground

👨‍👩‍👧‍👦 FAMILY PICKS

If you're planning something with the kids, save these:

🎃 Fruitville Grove Pumpkin Festival

🎭 Pinocchio

🐕 Barks & Brews: Howl-o-ween

🎬 Hocus Pocus under the stars

🐹 Capy Boo-Ra Bash

🎨 Creative Liberties Family Art Day

🎃 Trick or Treat on the Lake👻 Wellen Park Spooktacular

🎃 BooFest at Lakewood Ranch🏃 Runaway Pumpkin 5K & Family Fest

🌴 MY LOCAL PICKS

FOR A SLOW SATURDAY MORNING

Farmers market → coffee → Bayfront walk

FOR A FAMILY DAY

Pumpkin festival → lunch → beach or park

FOR A DATE NIGHT

Selby Gardens → dinner → live music or theater

FOR AN ART DAY

The Ringling → lunch → Sarasota Art Museum

FOR A SUNDAY IN LAKEWOOD RANCH

Farmers' Market → Waterside Place → dinner nearby

FOR HALLOWEEN

Pick your neighborhood event—or make an evening of Hocus Pocus under the stars.

🏡 SARASOTA REAL ESTATE NOTE

IT'S NOT JUST ABOUT THE HOUSE.

One of my favorite things about Sarasota is how different the communities can feel from one another.

Downtown Sarasota: Culture, restaurants, arts and an urban-coastal lifestyle.

South Gate & South Sarasota: Established neighborhoods with convenient access to downtown, beaches and everyday amenities.

Palmer Ranch: Newer communities, amenities and a suburban lifestyle.

Lakewood Ranch: Master-planned communities, newer homes, parks, schools and an active lifestyle.

Osprey & Nokomis: A quieter Gulf Coast feel with access to beaches and nature.

Venice: A charming, relaxed coastal lifestyle with its own downtown and beach community.

Longboat Key & Lido Key: A more private, coastal and elevated experience.

The best way to choose?

Experience the lifestyle before choosing the address.

📍 SAVE THIS GUIDE

Whether you're looking for a family outing, an art exhibition, a farmers market, live music, a workshop, a date night or something completely new:

Sarasota has plenty happening this October.

Save this guide, share it with a friend and go explore somewhere you haven't been yet.

FLORIDA HOMES WITH CATE

Miami • Sarasota

Helping professionals and families relocate to Florida and discover the communities that fit their lifestyle.

FIND YOUR FLORIDA

@FloridaHomesWithCate

Event dates and details can change. Please confirm directly with the event organizer before attending.