6402 Lakewood Ranch Blvd, Lakewood Ranch, FL 34202

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

Sarasota Art Museum, South Tamiami Trail, Sarasota, FL, 34236, United States

Take a stroll through the Sarasota Art Museum campus and discover the stories behind its stunning architecture. A great way to appreciate design and art in one morning!

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 with BodyBar Pilates Sarasota. No experience needed—just bring yourself and get ready to feel stronger!

Oscura, Bradenton

Rock out with Stick To Your Guns, No Cure, and Vomit Forth at Oscura in Bradenton. An intense night of live music you won't want to miss!

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 your heart pumping with this low-impact cardio class that blends resistance training—perfect for seniors and anyone just getting started.

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 just 45 minutes with body-weight exercises and high-energy intervals at The Bay Park. Perfect for all fitness levels!

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.

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 relaxation 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.

265 S Orange Ave, 265 South Orange Avenue, Sarasota, FL 34236, Sarasota, FL, 34236, US

Join the Sarasota Orchestra, Performing Arts Center, and Selby Gardens for a centennial celebration honoring 100 years of the Sarasota School and its lasting cultural impact.

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

Get moving with Yaël Campbell at this fun Zumba class at The Nest at The Bay Park. Dance, sweat, and have a blast!

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 active seniors and anyone just starting out. Join us at The Bay Park's beautiful Sunset Deck!

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

Join us for an hour of relaxing, mindful yoga at The Bay. Perfect for all levels—bring your mat and find your flow!

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.

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

Catch the sci-fi classic Arrival under the stars at The Bay's Oval for its 10th anniversary—free and perfect for a magical night out!

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.

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

Nationally touring stand-up comedian Nick Hoff, who's been on MTV, co-hosts a weekly SiriusXM show and was featured in Netflix's Comedy Festival. His debut album "Baby Daddy" hit #1 on the iTunes comedy charts, and he was hand-picked to open for Jeff Foxworthy and Larry the Cable Guy. Tickets $28.

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

Paddle out on the water and explore The Bay from a whole new perspective on this guided kayak tour. Perfect for beginners and seasoned paddlers alike!

Chidsey Library Building, 701 North Tamiami Trail, Sarasota, FL, 34236, US

Explore The Bay's most striking modern buildings on a guided tour with Architecture Sarasota. Learn the stories behind these architecturally significant gems that shaped our community.

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.

GT Bray Park, 5502 33rd Avenue Drive West, Bradenton

Join ghouls and gals at GT Bray Park for a spooktacular outdoor Halloween bash! This family-friendly celebration features local businesses, games, and treats for all ages.

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.

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

Paddle out on the water at The Bay Park and catch a stunning sunset from your kayak. A guided experience perfect for both beginners and seasoned paddlers.

925 North Lime Avenue,Sarasota,34237,US

Swap Halloween costumes, watch classic movies, and munch on snacks with friends at 925 North Lime Avenue. Perfect for a spooky pre-Halloween hangout!

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

Nationally touring stand-up comedian Nick Hoff, who's been on MTV, co-hosts a weekly SiriusXM show and was featured in Netflix's Comedy Festival. His debut album "Baby Daddy" hit #1 on the iTunes comedy charts, and he was hand-picked to open for Jeff Foxworthy and Larry the Cable Guy. Tickets $28.

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

Get fit fast with this 45-minute bootcamp using body-weight exercises and intervals to build strength and conditioning at The Oval.

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

Join us for a peaceful hour of yoga at The Bay Park—perfect for clearing your mind and centering your body. All levels welcome!

Hunsader Farms, 5500 C.R. 675, Bradenton

Join us for 35 years of fall fun at Florida's biggest pumpkin festival! Hayrides, live music, petting zoo, and more October weekends at Hunsader Farms.

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.

15571 Rutland Rd, Parrish, FL

A small farm day with a pumpkin patch, pony rides, face painting and hands-on animal fun. Admission is $15 (ages 2 and up). It also runs Oct 17 and 24.

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

Browse local vendors and handcrafted goods at this monthly outdoor market on Lakewood Ranch Main Street (October–April). Perfect for finding unique, quality items from talented local makers.

City of Anna Maria, Pine Avenue, Anna Maria Island

Join us for a day of live music, local food, crafts, and classic cars at Anna Maria Island's beloved street festival—free admission for all!

St. Armands Circle Park, 1 St. Armands Cir, Sarasota, FL, 34236, US

Celebrate creativity at the St. Armands Fall Festival of the Arts. Free admission. Runs Saturday and Sunday, Oct 17–18, 10:00 AM – 5:00 PM.

Selby Five Points Park, 1 Central Ave, Sarasota, FL, 34236, US

The 30th annual craft festival takes over Selby Five Points Park in downtown Sarasota, at the corner of Central Avenue and First Street. Runs Saturday and Sunday, Oct 17–18.

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.

Florida Railroad Museum, 12210 83rd Street East, Parrish

Hop aboard the Pumpkin Patch Express at the Florida Railroad Museum for a fun-filled fall adventure! Enjoy hay rides, crafts, games, and pick your own pumpkin to take home.

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

Join us the third Saturday of every month at the Village of the Arts for shopping, local galleries, artists, food, and family fun. It's the perfect excuse to stroll through Bradenton's creative heart!

Sarasota Art Museum, South Tamiami Trail, Sarasota, FL, 34236, United States

Join Judy Glickman Lauder at the Sarasota Art Museum for an engaging talk about what makes images truly memorable and stick with us.

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

A not-so-scary family Halloween celebration presented by Gulf Coast Community Foundation. Food trucks 4:30–7:45 PM, trick-or-treating, free pumpkin picking and decorating, and yard games 5:00–6:30 PM, then a sing-along family movie night, The Nightmare Before Christmas, 6:30–7:45 PM (bring a lawn chair). Costumes encouraged, not required. Pumpkins are first come, first served for the first 1,800 kids.

Sarasota Outboard Club, 1604 Ken Thompson Pkwy, Sarasota, FL 34236

A circus-themed night at the Sarasota Outboard Club with live music, circus food, kids' games, a best-dressed prize, raffles and a silent auction. Tickets from $12.51.

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.

Van Wezel Performing Arts Hall, Sarasota

Experience the magic of Fleetwood Mac's greatest hits performed live at Van Wezel Hall. A must-see tribute to one of rock's most iconic bands!

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

Nationally touring stand-up comedian Nick Hoff, who's been on MTV, co-hosts a weekly SiriusXM show and was featured in Netflix's Comedy Festival. His debut album "Baby Daddy" hit #1 on the iTunes comedy charts, and he was hand-picked to open for Jeff Foxworthy and Larry the Cable Guy. Tickets $28.

Hunsader Farms, 5500 C.R. 675, Bradenton

Celebrate fall at Florida's biggest pumpkin festival! Enjoy hayrides, a petting zoo, live music, and family fun at Hunsader Farms on select October weekends, 9am–5pm.

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.

St. Armands Circle Park, 1 St. Armands Cir, Sarasota, FL, 34236, US

Celebrate creativity at the St. Armands Fall Festival of the Arts. Free admission. Runs Saturday and Sunday, Oct 17–18, 10:00 AM – 5:00 PM.

Selby Five Points Park, 1 Central Ave, Sarasota, FL, 34236, US

The 30th annual craft festival takes over Selby Five Points Park in downtown Sarasota, at the corner of Central Avenue and First Street. Runs Saturday and Sunday, Oct 17–18.

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 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.

Palma Sola Botanical Park, 9800 17th Ave NW, Bradenton, FL 34209

The Pops Orchestra of Bradenton & Sarasota brings live jazz to Palma Sola Botanical Park for a new outdoor music experience. Relax under the trees, stroll the gardens and enjoy timeless jazz favorites. Wine, beer, seltzers, sodas, POPScorn and snacks are available to buy. Tickets: $65 VIP reserved table on the deck with 2 drink tickets, $50 lawn seating with chair included, $35 general admission (bring a chair or blanket). Use code "groovin" for $5 off lawn and GA tickets.

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

Nationally touring stand-up comedian Nick Hoff, who's been on MTV, co-hosts a weekly SiriusXM show and was featured in Netflix's Comedy Festival. His debut album "Baby Daddy" hit #1 on the iTunes comedy charts, and he was hand-picked to open for Jeff Foxworthy and Larry the Cable Guy. Tickets $28.

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.