Skip to main content

RSW Living Magazine

24 Things To Do In Southwest Florida This October & November

Oct 05, 2018 04:46AM ● By Emma Eldridge
Looking for something to do in the Months of October & November? We've got you covered with a wide array of events including holiday favorites, festivals, concerts, and more.

'Tis The Season For Holiday Events!

Halloween, Thanksgiving, and Christmas are all quickly approaching and we are so excited to share some wonderful holiday events with you! For Halloween, head to the 5th Annual Spooktacular Drink and Treat for Halloween, the 2018 Cape Coral Veterans Day Parade to honor our Veterans, and Naples Christmas on Third Street Tree Lighting Ceremony for some Christmas spirit.

Fort Myers Great Pumpkin Festival - start Oct 12 2018 0900AM

Fort Myers Great Pumpkin Festival - Oct 12, 2018 09:00AM

Fleamasters Fleamarket in Fort Myers will be hosting their annual Pumpkin' Palooza Great Pumpkin Festival! This event is 3 days of live music and family-friendly Halloween fall fun. Come ... Read More » 

5th Annual Spooktacular Drink and Treat - start Oct 20 2018 0700PM

5th Annual Spooktacular Drink and Treat - Oct 20, 2018 07:00PM

Take the exclusive trolleys around Cape Coral's Entertainment District, visiting various locations to enjoy a 2oz specialty drink sample and a piece of candy. The 2018 Spooktacular pub cr... Read More » 

Annual YMCA Fall Festival - start Oct 20 2018 0530PM

Annual YMCA Fall Festival - Oct 20, 2018 05:30PM

Annual YMCA Fall Festival Fun for the whole family! Invite your family & friends and join us for FREE FUN for the whole family, including: Family haunted houseCarnival gamesBounce hou... Read More » 

Halloween Themed Open House - start Oct 20 2018 0600PM

Halloween Themed Open House - Oct 20, 2018 06:00PM

We are proud to announce that we will be hosting our third Open House Event at J. Lee Salon Suites in Bonita Springs on October 20th from 6pm - 11pm!The party will be HALLOWEEN THEMED 🎃 S... Read More » 

Mummies At The Market  - start Oct 27 2018 0900AM

Mummies At The Market! - Oct 27, 2018 09:00AM

Mummies, ghouls, and little monsters delight - The Sarasota Farmers Market will be quite a sight! Come to trick or treat - while supplies last - stay for the costume contest - it will be... Read More » 

Cape Coral Boo Bash - start Oct 27 2018 0600PM

Cape Coral Boo Bash - Oct 27, 2018 06:00PM

Children ages 3 to 6 years old are invited to spend a spooky Saturday night at the William Austen Youth Center. Child will enjoy festive arts and crafts, music, cookie decorating, and gam... Read More » 

2018 Cape Coral Veterans Day Parade - start Nov 11 2018 0200PM

2018 Cape Coral Veterans Day Parade - Nov 11, 2018 02:00PM

Join us as the community honors our American Heroes and pays tribute to those who lost their lives, those who served honorably, and those who are still proudly serving our country. The Ve... Read More » 

Naples Christmas on Third Street Tree Lighting Ceremony - start Nov 19 2018 0600PM

Naples Christmas on Third Street Tree Lighting Ceremony - Nov 19, 2018 06:00PM

The Naples Mayor will be lighting the official Third Street South - Naples, Florida Christmas tree during the annual Tree Lighting Ceremony starting the tradition of Christmas on Third! E... Read More » 

Black Friday Pajama Party Pub Crawl - start Nov 23 2018 0700PM

Black Friday Pajama Party Pub Crawl - Nov 23, 2018 07:00PM

Put on those jammies and head to South Cape for a Black Friday pub crawl like no other! You'll take the trolleys to various hot spots to enjoy specialty drinks for just $2.50 at each plac... Read More » 

A Festival Here, A Fair There...

In case the latter months of the year didn't have enough great events, we've also picked out some festivals (like Oktoberfest), a fair (Fort Myers Fair At Fenway South), and a special event (SW-Florida Con). Take your pick and have some serious fun!

Oktoberfest - start Oct 19 2018 0400PM

Oktoberfest - Oct 19, 2018 04:00PM

The German-American Social Club of Cape Coral hosts FL's largest Oktoberfest in its 300' tent and 2-acre Bavarian Biergarten. Come see Ms. Oktoberfest 2018 and eat, drink, dance and schun... Read More » 

33rd Annual BaileyFest - start Oct 21 2018 1200PM

33rd Annual BaileyFest - Oct 21, 2018 12:00PM

Last year’s Baileyfest featured solo singers, bands and groups, dancers, a roaming magician, food, games and plenty of surprises. This year it’s going to be BETTER!Stop by Bailey’s Center... Read More » 

Craft Beer Fest - start Nov 10 2018 1200PM

Craft Beer Fest - Nov 10, 2018 12:00PM

Matanzas on the Bay on Fort Myers Beach is pleased to announce its first-ever craft beer event, “Matanzas Craft Beer Fest on the Bay,” on tap from noon to 4 p.m. on Saturday, Nov. 10. Bri... Read More » 

Fort Myers Fair At Fenway South - start Nov 09 2018 0500PM

Fort Myers Fair At Fenway South - Nov 09, 2018 05:00PM

The Fair at Fenway South is back for 2018 at JetBlue Park at Fenway South! There will be fair and carnival entertainment including the classics such as carnival rides, games, petting zoos... Read More » 

SW-FloridaCon - start Nov 18 2018 1000AM

SW-Florida Con - Nov 18, 2018 10:00AM

The SW-Florida Comic Con is back with a BANG! It’s the Pop-Culture mecca convention located in beautiful Southwest Florida. SW-Florida Comic-Con strives to be Florida's best and truest co... Read More » 

Musical Arts Galore!

What kind of music are you in the mood for? We've got it all! There's "An evening w/ Sinatra" show, the Gulf Coast Symphony: Halloween Spooktacular, John Tesh will be live in concert, and more!

Todd Snider - start Oct 11 2018 0700PM

Todd Snider - Oct 11, 2018 07:00PM

Todd Snider is an American singer-songwriter with a musical style that combines Americana, alt-country, and folk. Read More » 

Dinner  a show

Dinner & a show "An evening w/ Sinatra" impersonator Mike Dutra - Oct 13, 2018 06:00PM

Join us for a fun filled evening and fabulous food in our banquet room featuring Sinatra impersonator Michael Dutra. Dinner starts at 6:00 pm with the show beginning at 7:30 pm. Event pri... Read More » 

Peter Pan - Live on Stage - start Oct 13 2018 1100AM

Peter Pan - Live on Stage! - Oct 13, 2018 11:00AM

Join Peter on his adventure to Neverland, a magical island where there are no parents, no chores, and fairies and pirates rule! Introduce your children and grandchildren to the characters... Read More » 

Concert  Master Guitar Class With Dweezil Zappa - start Oct 26 2018 0700PM

Concert & Master Guitar Class With Dweezil Zappa - Oct 26, 2018 07:00PM

**MASTER GUITAR CLASS: $75** Ticket to show must be purchased in order to purchase a ticket for Master Guitar Class. Class ticket can be purchased as an upgrade after you select your show... Read More » 

Gulf Coast Symphony Halloween Spooktacular - start Oct 28 2018 0100PM

Gulf Coast Symphony: Halloween Spooktacular - Oct 28, 2018 01:00PM

Join us for a “not-so-spooky” Halloween concert that’s sure to be fun for the whole family! At 1:00pm, come dressed as your favorite storybook character for a costume contest and try out ... Read More » 

John Tesh - Live in Concert - start Nov 18 2018 0800PM

John Tesh - Live in Concert - Nov 18, 2018 08:00PM

Six music Emmys, two Grammy nominations, three gold records, a string of #1 radio hits, seven Public Television specials and 8 million records sold, John Tesh creates a delightful musical... Read More » 

Odds & Ends

We conclude our event picks with two contests (one for pets and one for humans) and two charity runs (2018 72 Hours to Key West and the Naples Thanksgiving Turkey Trot 5K). Fun AND challenging. Let's do this!

Promenade Pet Parade  Costume Contest - start Oct 25 2018 0500PM

Promenade Pet Parade & Costume Contest - Oct 25, 2018 05:00PM

Come in costume with your pawed or clawed best friends! We’ll have prizes for the best pet costume, best kid’s costume and best family or group costumes! We’ll be collecting pet food, bla... Read More » 

2018 72 Hours to Key West - start Nov 02 2018 0700AM

2018 72 Hours to Key West - Nov 02, 2018 07:00AM

Ft Myers Beach will come alive with up to 65 cyclists from Florida and beyond participating in the 280 mile, 3 day bike fest to tropical and sunny Key West, FL. With the Nations Finest Tr... Read More » 

American Championships Amateur Contest - start Nov 17 2018 0900AM

American Championships Amateur Contest - Nov 17, 2018 09:00AM

32nd Annual American Sand Sculpting Championships - Amateur Contest. The Amateur competition is a mixed team/solo event intended as a venue for beginning or advanced amateurs and is open ... Read More » 

Naples Thanksgiving Turkey Trot 5K - start Nov 22 2018 0730AM

Naples Thanksgiving Turkey Trot 5K - Nov 22, 2018 07:30AM

Gulf Coast Runners will be hosting their 6th annual Thanksgiving 5K on Thanksgiving! The run/walk event will be held at Cambier Park. The 5k course will wind through downtown Naples with ... Read More » 

Don't see your favorite included? Please share your event with us by posting to our calendar. It's free and a great way to spread the word!