6402 Lakewood Ranch Blvd, Lakewood Ranch, FL 34202

A casual, unstructured way to play tennis — participants organize their own games and matchups.

Dakin Dairy Farms, 30771 Betts Road, Myakka City

Get into the harvest spirit at Dakin Dairy Farms with hayrides, farm animal experiences, pumpkin cannons, live music, food trucks, and more fun for the whole family!

Florida Railroad Museum, 12210 83rd Street East, Parrish

All aboard for fall fun! Ride the Pumpkin Patch Express to the museum's pumpkin patch, complete with hay rides, crafts, games, and a pumpkin to take home.

The Green at UTC, 140 University Town Center Dr, Sarasota, FL 34243

The annual Pumpkin Patch, presented by Detwiler's Farm Market, takes over The Green. Every pumpkin purchase benefits Nate's Honor Animal Rescue Center, a Lakewood Ranch nonprofit caring for homeless and at-risk dogs and cats. Pumpkins available while supplies last.

Common Ground at The Bay Park, 1055 Blvd of the Arts, Sarasota, FL, 34236, US

Join a free hour of mat pilates at Common Ground at The Bay Park. A great way to strengthen your body and start your day right!

Historic Spanish Point, 401 N Tamiami Trail, Osprey, FL 34229

An illuminated evening walk through the Historic Spanish Point campus, with two entry times (6:30 and 7:45 p.m.); event ends at 9 p.m. Runs nightly October 1–31. Free for members and kids 4 and under; $12 member guests and ages 5–17; $20 adults.

Manatee Performing Arts Center, 502 Third Ave West, Bradenton

Experience the electrifying stage adaptation of Stephen King's Carrie at the Manatee Performing Arts Center. This haunting musical explores bullying and belonging with intense drama and a powerful score.

1561 Lakefront Drive, Sarasota, FL 34240

Join Florida Provisions every Monday for Bingo Night — cold beer and prizes.

1570 Lakefront Drive, Sarasota, FL 34240

Gather your friends, challenge your brain, and savor a beer at Good Liquid Brewing Company for Trivia Night every Monday.

5304 Holmes Blvd, Holmes Beach, FL 34217

Sing your heart out every Monday at The Freckled Fin Irish Pub on Anna Maria Island.

Sunset Deck at The Bay Park, 1055 Blvd of the Arts, Sarasota, FL, 34236, US

Get moving with a low-impact cardio and resistance class perfect for seniors and beginners. Meet at Sunset Deck at The Bay Park!

Roser Church, 512 Pine Ave, Anna Maria, FL 34216

Fresh food, local art, and good vibes every Tuesday at the Anna Maria Community Farmers Market.

The Green at UTC, 140 University Town Center Dr, Sarasota, FL 34243

The annual Pumpkin Patch, presented by Detwiler's Farm Market, takes over The Green. Every pumpkin purchase benefits Nate's Honor Animal Rescue Center, a Lakewood Ranch nonprofit caring for homeless and at-risk dogs and cats. Pumpkins available while supplies last.

Sarasota Garden Club at The Bay Park, 1131 Boulevard of the Arts, Sarasota, FL, 34236, US

Get stronger in 45 minutes with this energizing bootcamp using body-weight exercises and intervals. Join us at Sarasota Garden Club at The Bay Park!

The Nest at The Bay, 1055 Boulevard of the Arts, Sarasota, FL, 34236, US

Join a guided mindful walk at sunset along The Bay and soak in the beauty of Sarasota's waterfront. A peaceful way to end your day.

8130 Lakewood Main Street, Suite 104, Bradenton, FL 34202

A night of singing, dancing, and prizes set to your favorite hits, paired with scratch-kitchen food, handcrafted cocktails, and craft beer.

Historic Spanish Point, 401 N Tamiami Trail, Osprey, FL 34229

An illuminated evening walk through the Historic Spanish Point campus, with two entry times (6:30 and 7:45 p.m.); event ends at 9 p.m. Runs nightly October 1–31. Free for members and kids 4 and under; $12 member guests and ages 5–17; $20 adults.

10719 Rodeo Dr, Lakewood Ranch, FL

Hosted by Steve-O, general trivia covering current events, sports, holidays, and more — compete for bragging rights, pitchers of beer, and gift cards.

1561 Lakefront Drive, Suite 102 and 103, Sarasota, FL 34240

A laid-back night of singing your favorite songs, cheering on friends, and half-off margaritas.

10719 Rodeo Dr, Lakewood Ranch, FL 34202

Free Texas Hold 'Em — no cost to play. Weekly winner takes home a $50 Ed's gift card, plus a chance at a seat in the One-Eyed Jacks tournament at Sarasota Kennel Club.

Sarasota Garden Club, 1131 Boulevard of the Arts, Sarasota, FL, 34236, US

Join Gail at the Sarasota Garden Club for a peaceful session of Tai Chi and Qigong—ancient Chinese practices perfect for balance, calm, and wellness.

6402 Lakewood Ranch Blvd, Lakewood Ranch, FL 34202

A casual, unstructured way to play tennis — participants organize their own games and matchups.

1800 Gulf Drive S, Bradenton Beach, FL 34217

An upscale beach market at the south end of Anna Maria Island.

The Green at UTC, 140 University Town Center Dr, Sarasota, FL 34243

The annual Pumpkin Patch, presented by Detwiler's Farm Market, takes over The Green. Every pumpkin purchase benefits Nate's Honor Animal Rescue Center, a Lakewood Ranch nonprofit caring for homeless and at-risk dogs and cats. Pumpkins available while supplies last.

7301 Island Cove Terrace, Lakewood Ranch, FL 34240

Roulette-style pickup volleyball for players ready to jump in and play without instruction.

The Nest at The Bay Park, 1055 Blvd of the Arts, Sarasota, FL, 34236, US

Dance the evening away with Donald Frison, the Westcoast Black Theatre Troupe's resident choreographer, at The Nest at The Bay Park. A night of movement and fun you won't forget!

Historic Spanish Point, 401 N Tamiami Trail, Osprey, FL 34229

An illuminated evening walk through the Historic Spanish Point campus, with two entry times (6:30 and 7:45 p.m.); event ends at 9 p.m. Runs nightly October 1–31. Free for members and kids 4 and under; $12 member guests and ages 5–17; $20 adults.

McCurdy's Comedy Theatre, 1923 Ringling Blvd, Sarasota, FL 34236

Stand-up comedian Basile brings his act to McCurdy's for four nights. His credits include HBO, Showtime, Comedy Central, Dry Bar Comedy and the Tonight Show, plus voice work as Universal Studios' Bullwinkle J. Moose. He was recently Emmy-nominated for his voice work on ESPN's 30 for 30.

Manatee Performing Arts Center, 502 Third Ave West, Bradenton

Multiple perfomances between 10-15 and 11-01, check box office for days and showtimes. Experience the chilling, electrifying stage adaptation of Stephen King's Carrie at the Manatee Performing Arts Center. This powerful musical explores bullying and isolation through intense drama and a gripping score.

Sunset Deck at The Bay Park, 1055 Blvd of the Arts, Sarasota, FL, 34236, US

Get your heart pumping with this low-impact cardio and resistance class perfect for seniors and beginners. Meet at Sunset Deck at The Bay Park!

7500 Island Cove Terrace, Sarasota, FL 34240

A fun morning of casual cornhole for all skill levels — grab a partner or go solo, beanbags and boards provided.

The Green at UTC, 140 University Town Center Dr, Sarasota, FL 34243

The annual Pumpkin Patch, presented by Detwiler's Farm Market, takes over The Green. Every pumpkin purchase benefits Nate's Honor Animal Rescue Center, a Lakewood Ranch nonprofit caring for homeless and at-risk dogs and cats. Pumpkins available while supplies last.

Common Ground at The Bay Park, 1055 Blvd of the Arts, Sarasota, FL, 34236, US

Unwind with yoga teacher and sound healer Petra Ratner for a soothing sound bath experience surrounded by nature at The Bay Park.

Floridays Woodfire Grill & Bar, 12332 Manatee Ave. West, Bradenton

Catch live music from local and visiting artists at Floridays Woodfire Grill & Bar. Great vibes, good food, and tunes!

Floridays Woodfire Grill & Bar, 12332 Manatee Ave W, Bradenton, FL 34209

Enjoy live music by various artists every Thursday and Saturday evening at Floridays Woodfire Grill & Bar.

Historic Spanish Point, 401 N Tamiami Trail, Osprey, FL 34229

An illuminated evening walk through the Historic Spanish Point campus, with two entry times (6:30 and 7:45 p.m.); event ends at 9 p.m. Runs nightly October 1–31. Free for members and kids 4 and under; $12 member guests and ages 5–17; $20 adults.

The Oval at The Bay, 1055 Blvd of the Arts, Sarasota, FL, 34236, US

Celebrate Rocky's 50th anniversary with a free outdoor screening under the stars at The Bay. Grab your friends and relive this iconic classic!

Manatee Performing Arts Center, 502 Third Ave West, Bradenton

Follow Evan Hansen, a shy teen navigating an unexpected tragedy, as his search for connection spirals into a web of lies. A moving musical about growing up and finding your place in the world.

McCurdy's Comedy Theatre, 1923 Ringling Blvd, Sarasota, FL 34236

Stand-up comedian Basile brings his act to McCurdy's for four nights. His credits include HBO, Showtime, Comedy Central, Dry Bar Comedy and the Tonight Show, plus voice work as Universal Studios' Bullwinkle J. Moose. He was recently Emmy-nominated for his voice work on ESPN's 30 for 30.

3000 Ringling Blvd, Sarasota, FL 34237

Runs Oct 16–18, Oct 22-25, Oct 29-Nov 1. One $28 general admission ticket covers the music, Halloween atmosphere and entertainment, plus both haunted attractions: Virus and Tomb of Terror.

Kayak Launch at The Bay Park, 1055 Blvd of the Arts, Sarasota, FL, 34236, US

Paddle out on a guided kayak tour and explore the beautiful waters around The Bay Park. A perfect way to see Sarasota from the water!

Sarasota Fairgrounds, Robarts Arena, 3000 Ringling Blvd, Sarasota, FL 34237

An indoor vintage shopping extravaganza with passionate pickers, makers, collectors, creators, and artisans. Admission is $8, with group deals of 2 for $12 or 4 for $20, and kids under 16 are free. Call 941-365-0818 for details.

Florida Maritime Museum, 4415 119th Street West, Cortez

Dive into a 3-hour batik workshop where you'll learn this beautiful art form and create your own 14x14 design to take home. Perfect for adults and teens 15+.

1800 Gulf Drive S, Bradenton Beach, FL 34217

An upscale beach market at the south end of Anna Maria Island.

The Green at UTC, 140 University Town Center Dr, Sarasota, FL 34243

The annual Pumpkin Patch, presented by Detwiler's Farm Market, takes over The Green. Every pumpkin purchase benefits Nate's Honor Animal Rescue Center, a Lakewood Ranch nonprofit caring for homeless and at-risk dogs and cats. Pumpkins available while supplies last.

Near Spanish Rocks, Holmes Beach, FL 34217 (park near 33rd Street, or at Manatee Public Beach and walk left along the beach)

A weekly gathering for drumming, dancing, and community as the sun goes down on Anna Maria Island. The circle begins one hour before sunset, so the exact start time shifts through the season.

McCurdy's Comedy Theatre, 1923 Ringling Blvd, Sarasota, FL 34236

Stand-up comedian Basile brings his act to McCurdy's for four nights. His credits include HBO, Showtime, Comedy Central, Dry Bar Comedy and the Tonight Show, plus voice work as Universal Studios' Bullwinkle J. Moose. He was recently Emmy-nominated for his voice work on ESPN's 30 for 30.

Historic Spanish Point, 401 N Tamiami Trail, Osprey, FL 34229

An illuminated evening walk through the Historic Spanish Point campus, with two entry times (6:30 and 7:45 p.m.); event ends at 9 p.m. Runs nightly October 1–31. Free for members and kids 4 and under; $12 member guests and ages 5–17; $20 adults.

3000 Ringling Blvd, Sarasota, FL 34237

Runs Oct 16–18, Oct 22-25, Oct 29-Nov 1. One $28 general admission ticket covers the music, Halloween atmosphere and entertainment, plus both haunted attractions: Virus and Tomb of Terror.

The Oval, 1055 Blvd of the Arts, Sarasota, Florida, 34236

Channel your inner Rocky with high-energy punching, kicking, and sweating in this special Les Mills BODYCOMBAT™ class! Join Instructor Michelle Cook at The Oval on Saturday, October 24 to celebrate Rocky's 50th anniversary.

The Oval at The Bay, 1055 Blvd of the Arts, Sarasota, FL, 34236, US

Get strong in 45 minutes with this high-energy bootcamp using body-weight exercises and intervals. Meet us at The Oval at The Bay!

Common Ground at The Bay Park, 1055 Blvd of the Arts, Sarasota, FL, 34236, US

Join us for an hour of mindful yoga at The Bay—perfect for finding your flow and center. Classes held at Common Ground at The Bay Park.

Kayak Launch at The Bay Park, 1055 Blvd of the Arts, Sarasota, FL, 34236, US

Paddle through beautiful Sarasota Bay on a guided kayak tour launching from The Bay Park. Perfect for exploring local waterways and spotting wildlife!

Hunsader Farms, 5500 C.R. 675, Bradenton

Pick your pumpkin and soak up fall fun at Hunsader Farms' 35-year tradition! Enjoy hayrides, live music, a petting zoo, and more across three October weekends.

Sarasota Fairgrounds, Robarts Arena, 3000 Ringling Blvd, Sarasota, FL 34237

An indoor vintage shopping extravaganza with passionate pickers, makers, collectors, creators, and artisans. Admission is $8, with group deals of 2 for $12 or 4 for $20, and kids under 16 are free. Call 941-365-0818 for details.

Old Main Street & 12th Street W, Bradenton, FL 34205

Fresh produce, local art, music, and free family activities from local farmers, artisans, and chefs on Old Main Street.

Lakewood Ranch Main Street, 8100 Lakewood Ranch Blvd, Lakewood Ranch

Browse handcrafted goods and local finds at this monthly outdoor market on Lakewood Ranch Main Street. Open October through April on select Saturdays—a perfect spot for unique gifts and neighborhood treasures.

Fruitville Grove, 7410 Fruitville Rd, Sarasota, FL 34240

The 38th annual Fruitville Grove Pumpkin Festival returns every weekend in October with a pumpkin patch, petting zoo, local vendor booths, and circus performances. Admission and some activities are free; other activities range from $1–$10.

Dakin Dairy Farms, 30771 Betts Rd, Myakka City, FL 34251

A full day on the farm with a corn maze, hayrides, live music, food trucks, animal interactions, and a pumpkin cannon. $20 per person, kids 5 and under free, free parking.

The Green at UTC, 140 University Town Center Dr, Sarasota, FL 34243

The annual Pumpkin Patch, presented by Detwiler's Farm Market, takes over The Green. Every pumpkin purchase benefits Nate's Honor Animal Rescue Center, a Lakewood Ranch nonprofit caring for homeless and at-risk dogs and cats. Pumpkins available while supplies last.

Village of the Arts, 1227 12th St W, Bradenton

Head to the Village of the Arts on the third Saturday for a fun day of shopping, local art, great food, and activities. Stroll through galleries, meet artists, and enjoy the vibrant community atmosphere.

Floridays Woodfire Grill & Bar, 12332 Manatee Ave. West, Bradenton

Catch great live music at Floridays Woodfire Grill & Bar on Manatee Ave.—the perfect spot for good food, drinks, and local talent.

AMI Paddleboard and Kayak Adventures, parking on the right side of the Manatee Bridge next to The Compass Hotel. Paddle through Neal Preserve/South Perico, Bradenton

AMI Paddle and The Center of Anna Maria Island host a Halloween adventure on the water for kids and families. Paddle through the mangroves of Neal Preserve for an evening of fun, fright and a little mystery. This first trip starts around sunset, before it gets completely dark. Ages 17 and under, or adults accompanying children who can't paddle independently. Space is limited and advance registration is required.

Floridays Woodfire Grill & Bar, 12332 Manatee Ave W, Bradenton, FL 34209

Enjoy live music by various artists every Thursday and Saturday evening at Floridays Woodfire Grill & Bar.

McCurdy's Comedy Theatre, 1923 Ringling Blvd, Sarasota, FL 34236

Stand-up comedian Basile brings his act to McCurdy's for four nights. His credits include HBO, Showtime, Comedy Central, Dry Bar Comedy and the Tonight Show, plus voice work as Universal Studios' Bullwinkle J. Moose. He was recently Emmy-nominated for his voice work on ESPN's 30 for 30.

Historic Spanish Point, 401 N Tamiami Trail, Osprey, FL 34229

An illuminated evening walk through the Historic Spanish Point campus, with two entry times (6:30 and 7:45 p.m.); event ends at 9 p.m. Runs nightly October 1–31. Free for members and kids 4 and under; $12 member guests and ages 5–17; $20 adults.

3000 Ringling Blvd, Sarasota, FL 34237

Runs Oct 16–18, Oct 22-25, Oct 29-Nov 1. One $28 general admission ticket covers the music, Halloween atmosphere and entertainment, plus both haunted attractions: Virus and Tomb of Terror.

AMI Paddleboard and Kayak Adventures, parking on the right side of the Manatee Bridge next to The Compass Hotel. Paddle through Neal Preserve/South Perico, Bradenton

Paddle through the mangroves of Neal Preserve after dark with AMI Paddle and The Center of Anna Maria Island. An evening of fun, fright and a little mystery. Ages 18+. Space is limited and advance registration is required: register at centerami.org/events or call The Center at 941.778.1908.

Hunsader Farms, 5500 C.R. 675, Bradenton

Pick your pumpkin and celebrate fall at Florida's largest family festival! Enjoy hayrides, a petting zoo, live music, and more on select October weekends (9am–5pm).

Sarasota County Fairgrounds, Potter Building, 3000 Ringling Blvd, Sarasota, FL 34237

A bird show and sale with exotic animals, cages, toys, feed, and perches, plus food trucks on site.

Mixon Fruit Farms, 2525 27th St E, Bradenton, FL 34208

A weekly Sunday market at Mixon Fruit Farms, running through the season from late September to the end of May.

Fruitville Grove, 7410 Fruitville Rd, Sarasota, FL 34240

The 38th annual Fruitville Grove Pumpkin Festival returns every weekend in October with a pumpkin patch, petting zoo, local vendor booths, and circus performances. Admission and some activities are free; other activities range from $1–$10.

Dakin Dairy Farms, 30771 Betts Rd, Myakka City, FL 34251

A full day on the farm with a corn maze, hayrides, live music, food trucks, animal interactions, and a pumpkin cannon. $20 per person, kids 5 and under free, free parking.

Lakewood Ranch Main Street, Lakewood Ranch, FL

Local produce, baked goods, and live music every Sunday at Lakewood Ranch Main Street.

1800 Gulf Drive S, Bradenton Beach, FL 34217

An upscale beach market at the south end of Anna Maria Island.

The Oval Parking Lot at The Bay Park, 1055 Blvd of the Arts, Sarasota, FL, 34236, US

Sample delicious bites from local Sarasota restaurants, sip on drinks, and enjoy live music at The Bay Park. A perfect evening celebrating the flavors of our community!

The Bay, 1055 Blvd of the Arts, Sarasota, FL, 34236

Join us at The Bay for Taste of The Bay: Kettle of Fish, where you can sample delicious fresh seafood and local flavors in a beautiful waterfront setting.

The Green at UTC, 140 University Town Center Dr, Sarasota, FL 34243

The annual Pumpkin Patch, presented by Detwiler's Farm Market, takes over The Green. Every pumpkin purchase benefits Nate's Honor Animal Rescue Center, a Lakewood Ranch nonprofit caring for homeless and at-risk dogs and cats. Pumpkins available while supplies last.

3115 Lakewood Ranch Blvd, Suite 110, Bradenton, FL 34211

A relaxed Sunday afternoon with a food truck (2-6 PM) and open mic featuring local musicians and performers (3-6 PM). Tours and tastings available 12-3 PM by reservation.

Van Wezel Performing Arts Hall, Sarasota

Step into a dark and dazzling world at Van Wezel Performing Arts Hall—this circus spectacular blends acrobatics, artistry, and gothic drama for an unforgettable night.

Historic Spanish Point, 401 N Tamiami Trail, Osprey, FL 34229

An illuminated evening walk through the Historic Spanish Point campus, with two entry times (6:30 and 7:45 p.m.); event ends at 9 p.m. Runs nightly October 1–31. Free for members and kids 4 and under; $12 member guests and ages 5–17; $20 adults.

3000 Ringling Blvd, Sarasota, FL 34237

Runs Oct 16–18, Oct 22-25, Oct 29-Nov 1. One $28 general admission ticket covers the music, Halloween atmosphere and entertainment, plus both haunted attractions: Virus and Tomb of Terror.

Siesta Beach, 948 Beach Rd, Sarasota, FL 34242

A vibrant weekly drum circle on Siesta Beach every Sunday evening, beginning an hour before sunset. Locals and visitors gather for rhythm, dancing, and sunset on the sand.