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October 2023 The Best Events and Festivals in Florida

The Best Events and Festivals in Florida

The Best in Florida Festivals and Events October 2023

Florida hosts some amazing events and festivals. Each month I hope to take a look at a dozen or so of these in hopes of bringing you fun, exciting, and unexpected ways to enjoy our state.

If you have an event or know of one coming up that you feel should be highlighted, please drop me a line with as much information as you can, including a website. I’ll be glad to include your suggestions in future posts.

Posts are listed in date order.

I have purposefully not included Oktoberfest and Halloween related events in this post.

October 6-8      Destin Seafood Festival             Destin

This event which features seafood, music, art, and more serves as a fundraiser for the Destin Charter Boat Association, a not-for-profit organization formed in 1954. More than 70 vendors, five music stages, and seafood galore.





Boots, Bulls, and Barrels October 7, 2023

October 7         Boots, Bulls & Barrells              Kissimmee

An intense event that combines the thrill of bull riding with the fast agility of barrel racing. This tournament-style event brings together professional bull riders and skilled equestrians in a competition of adrenaline and skill.

The annual Silver Spurs Rodeo is one of the top rodeos in the country so this event promises to be excellent.

Take a video tour of the history of the Silver Spurs Rodeo below.




Green Cove Springs Soul Food FestivalOctober 7         Green Cove Springs Soul Food & Music Festival

Enjoy an amazing day of southern cooking, live music, dancing, children’s activities, local artists, specialty vendors, and more.



Winter Park Autumn Art Festival  

October 7-8      Autumn Art Festival         Winter Park

The Winter Park Autumn Art Festival is the only juried fine art festival exclusively featuring Florida artists.

The Winter Park Chamber of Commerce is proud to host the festival on the second weekend in October each year. The community-oriented sidewalk show presents quality visual art and live entertainment the whole family can enjoy. The festival is held in beautiful Central Park located along historic Park Avenue in downtown Winter Park.

The festival is open from 9:00 a.m. – 5:00 p.m. both days.

Admission is free!




Florida Birding & Nature FestivalOctober 12-15  Florida Birding & Nature Festival    Apollo Beach

Four days of field and boat trips, expert seminars, keynote speakers, and a free nature expo with more than 20 vendors and organizations. There October are charges for certain portions of this festival.




October 14                McIntosh 1890s Festival            McIntosh

Named for the decade when the community began to flourish, this festival has grown to more than 200 vendors with tens of thousands of visitors. Enjoy music, food, shopping, arts and crafts, jewelry, and more while enjoying local Victorian charm.


October 19-22           Biketoberfest            Daytona Beach

Motorcycle enthusiasts come together during the four-day rally each year to enjoy beautiful Florida weather, live music, motorcycle racing at Daytona International Speedway, and miles of scenic rides along famous A1A, historic Main Street or the scenic Loop. Come experience the Southeast’s best motorcycle rally featuring motorcycle shows, custom bike builds and hundreds of the industry’s top vendors throughout Daytona Beach.



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October 21                Sanford Jazz in the Park         Sanford

Come out to the 6th annual Jazz in the Park at Centennial Park. This family oriented events features live music, food trucks, vendors, and a cash bar. This music festival is presented by Ladies 327 in association with Historic Downtown Sanford.

Sanford, Florida Jazz in the Park October 21, 2023


October 21-22           Cedar Key Seafood Festival      Cedar Key

Now it’s 53rd year, this year’s festival will celebrate the year of the clam. The festival features seafood, more than arts and crafts vendors, music, and an amazing Saturday morning parade you won’t want to miss.

Renowned for its delectable seafood offerings, vibrant arts and crafts scene, and lively live music performances, the Cedar Key Seafood Festival promises visitors an unforgettable weekend full of fun and flavors. 

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October 25-29           Fort Lauderdale International Boat Show

With plans for multiple show locales, more than 1,300 boats, 1,000 brands, and 100,000 attendees, this is the boat show for any marine enthusiast. Buy your tickets in advance online (HINT, HINT, they aren’t cheap).


Naples Stone Crab Festival

October 27-29           Naples Stone Crab Festival       Naples

A Naples tradition for more than a decade, enjoy stone crab, other seafood, live entertainment, arts and crafts vendors, and more.


October 28       Florida Territory Living History      Dade City

A living history event depicting Florida history before 1845: pre-history/archeological, pre-Columbian (15th Century and before), Spanish Colonial Period, Seven Years/Revolutionary War, Patriot War/War of 1812, Seminole Wars.
Tickets at the Gate Only.
Florida Territory Living History Day at Pioneer Florida Museum and Village


Thousands attend the Mt. Dora Craft Fair, consistently ranked one of the best craft fairs in the country.October 28-29   Mount Dora Fall Craft Fair      Mount Dora

Consistently voted in the top 5 craft fairs across the country by Sunshine Artist Magazine Subscription

The downtown streets come alive with almost 400 of the best exhibitors in the country ready to show and sell their fine and fun crafts at this annual event. Festival food, music, beer, wine, cocktails and some special guest appearances will round out the event.




October 28-29           Lake Wales Pioneer Days Festival

Happening in Lake Wailes Park, this event will feature reenactors and historic demonstrations, more than 60 craft market vendors, local food vendors, community partners, and be sure to nominate someone for “Pioneer of the Year.”


October 29                Tavares Trailblazers                 Tavares

Join historian Richard Lee Cronin at the Tavares History Research Center for a presentation celebrating some of the exceptional individuals and the roles each played in the development of the town.

Tavares Trailblazer October 29, 203

Thank you to Bob Grenier for alerting me to this event! Remember, if you have an event that you would like me to include in future posts, drop me a line with the information. It’s free!

This post may contain affiliate links. If you click these links and make a purchase, I may receive a small commission. This commission does not affect any price that you pay. All views and opinions provided are my own and are never influenced by affiliate programs or sponsors providing products. 

Personalized Push Pin Travel Maps

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A History of the Monument of States in Kissimmee, Florida

Located just south of downtown Kissimmee, near the intersection of Lakeview Drive and Monument Avenue visitors will find the Monument of States.

The Monument of States was the brainchild of Dr. Charles W. Bressler-Pettis. As Joy Dickinson has written about Bressler-Pettis, “…one Central Floridian was galvanized to express the nation’s unity in a singular, towering vision: a monument in his winter home, Kissimmee, that would express the bond between states and continue to inspire tourists to stop, look up and wonder.” (Patriotism)

Monument of States

Monument of States in Kissimmee, FL

The Monument of States as it currently stands has several origin stories. Some claim it dates back to 1935 (Doctors Love) while most state that it was conceived in response to the Japanese bombing of Pearl Harbor in 1941. (National Register, Patriotism)

Dr. Charles W.  Bressler-Pettis was an active member of the Lions Club and Kissimmee All-States Tourist Club and in the early 1940s partnered with J. C. Fisher to design a monument as a symbol of American unity in a time of war.

To learn more about the war that inspired this incredibly unique and beautiful monument, I recommend a subscription to World War II magazine. World War II magazine covers every aspect of history’s greatest modern conflict with vivid, revealing, and evocative writing from top historians and journalists

Promotion for the monument began immediately. By the end of December 1941, an Honor Role of Cement Donors had been established. Here, individuals and businesses who supplied a bag of concrete were thanked for their contribution. A pamphlet was produced listing 507 concrete donors.  (National Register)

Honor Roll of Cement Donors dated December 21, 1941, just days after the bombing of Pearl Harbor

Groundbreaking occurred on January 11, 1942 with the cornerstone being set in place. Volunteer labor, much of it coming from the Kissimmee All States Tourist Club, kept the project in motion. Bressler-Pettis collected rocks from donors across the country for use in the monument. Bressler-Pettis also supplied many rocks from his own travels.  He wrote letters to state governors asking for representative rocks. President Franklin D. Roosevelt contributed a stone from his Hyde Park, New York residence.

Once complete, the monument consisted of more than 1,500 stones from the then 48 states and 21 countries. It contained 21 tiers and reached 50 feet tall. The eagle atop the monument has a wingspan of six-feet. The base of the monument measures sixteen square feet and the top tier is only  two and one half square feet. The foundation for the monument is three feet thick, twenty-two square feet, and weighs approximately 100,000 pounds. (National Register, Patriotism)


Senator Claude Pepper was on hand for the monument dedication
A time capsule was placed on the 50th anniversary of the monument dedication. It is to be opened on the 100th anniversary.

United States Senator Claude Pepper was on hand for the monument dedication on March 28, 1943. In the years since the monument has been the location of many ceremonies including a 50-year celebration on March 28, 1993 when officials placed a time capsule at the monument. The capsule will be opened on the 100th anniversary of the dedication.

Cultural Importance

The Monument of States represents a time in Florida tourism before the onslaught of theme parks and mass commercialization. The effort to create this monument brought together a community toward a common goal in a way that cartoon characters and comic book heroes never will.

For those interested in the significance of this monument to visitors, there are seemingly dozens of different postcard images of the Monument of States. This collection of images is important first, in placing the monument in time but also in documenting its early appearance. The diversity of images and the often handwritten messages sent home, show the impact the monument had on visitors. They felt this was an image worthy of sharing with the folks “back home.” In the era before social media, postcards were a convenient way of “tagging” where you were for your friends to follow.

In the years before Disney, those days of the road trip, Stuckey’s, “are we there yet,” and the roadside attraction, the Monument of States served as a tourist draw. In describing the monument and it’s relevance, the National Register of Historic Places Registration Form states, “It retains integrity of design, materials, workmanship, feeling and association with the early history and tourism efforts in Kissimmee, and continues to serve as a draw for both residents and visitors alike.” (National Register) The monument was officially added to the National Register of Historic Places in December 2015.


120 Minute Open Jump at a Trampoline Park in Kissimmee – $50.85

Get ready for a high-flying good time at the 120 Minute Open Jump at a Trampoline Park in Kissimmee!


Dr. Charles W. Bressler-Pettis

Just who was Dr. Bressler-Pettis? Charles was born on February 12, 1889 in Grant City, Missouri to parents Manuel and Nellie A. Bressler. When or why Charles changed his surname to Bressler-Pettis is unknown. We do know that Pettis was his mother’s maiden name. The first known recorded use of this new name is on a 1922 passport application. (Osceola History)

Young Charles was encouraged to become a medical doctor. At the urging of his family, after graduating from the University of Missouri he attended Harvard Medical School, graduating in 1917 and served his internship in Boston.

During World War I Charles served in the British army medical corps before joining the United States army medical corps later in the fight. During the war Charles visited a wealthy uncle who was living in Nice, France at the time. After the war he returned to France where he became the personal physician for his uncle. Charles was to receive a large, lifetime income from the estate of his uncle.

After returning to the States, Charles met, and married, Laura Mead. After their January 1927 wedding they embarked on a long honeymoon, logging over 78,000 miles by automobile.

A plaque in honor of Charles Bressler-Pettis, the man behind the Monument of States

Charles suffered a fatal heart attack while already in the hospital, on May 12, 1954. It is often repeated that Bressler-Pettis’s ashes are buried at the Monument of States. There is some truth to this story. After Charles’s death, his wife made request of the Kissimmee City Commission to be allowed to inter Charles’ ashes at the base of the Monument of States; a request that was approved by special ordinance.  It appears however that Mrs. Bressler-Pettis may have reconsidered. The website, Findagrave, shows a listing for Charles W. Bressler-Pettis in Grant City Cemetery, in Grant City, Missouri, the city where Charles was born. (Findagrave, Osceola History) Both stories are true. I have found reference that part of his ashes were buried in each location. This seems like a reasonable answer based upon the City Commission going to the trouble of amending local ordinances. (Memorialogy, National Register)

A circa 1943 postcard image of the Monument of States. Image courtesy State Archives of Florida
Postcard image circa 1950. Courtesy State Archives of Florida
Photo image of the Monument of States 2017.
Even after completion donations of rocks kept arriving such as this from Disney Studio’s Gem and Mineral Society. Photo 2017


“Doctors Love of Area Fueled Drive for Monument.” Orlando Sentinel. July 22, 1990.



National Register of Historic Places Registration Form.

Osceola History.

“Patriotism After Pearl Harbor Fueled Creation…” Orlando Sentinel. December 12, 2021.

Sandler, Roberta. A Brief Guide to Florida’s Monuments and Memorials. Gainesville: University Press of Florida, 2008.

This post may contain affiliate links. If you click these links and make a purchase, I may receive a small commission. This commission does not affect any price that you pay. All views and opinions provided are my own and are never influenced by affiliate programs or sponsors providing products.


World War II

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Keep up with some the best short form writing on World War II with a subscription to the bi-monthly magazine World War II click the link or the photo to the left for exclusive savings and have it delivered right to your door.

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Bataan-Corregidor World War II Monument in Kissimmee, Florida

The fall of Bataan and Corregidor in the Philippine islands to Japanese forces were arguably the
worst defeats of United States forces during World War II.

General Douglas MacArthur. Photo courtesy Library of Congress

In VERY simplified form, General Douglas MacArthur and his troops in the Philippines were tasked with holding back the advancing Japanese Imperial Army. Their objective was to keep Japan out of the American territory of the Philippine Islands.

General MacArthur consolidated his troops on the Bataan Peninsula where a combined force of American and Filipino troops were able to hold back the onslaught of Japanese troops for three months, a crucial delay to the plans of Japanese leadership.

After escaping Corregidor during the night of March 12, 1942, General MacArthur later uttered his famous “I Shall Return” speech, a promise he made good on in 1944.

On April 9, 1942, Bataan fell. Major General Edward P. King surrendered the allied troops to Major General Kameichiro Nagano, beginning what would become a further nightmare for the already hungry and weary troops. The surrender of Bataan would lead to the surrender of Corregidor less than a month later.

A Map Showing the Route of the Bataan Death March


It was at this point, where Japanese soldiers ordered their prisoners into a series of marches that collectively are known as the Bataan Death March. This march was approximately 65 miles with little to no food and water.

Online sources vary as to the number of prisoners and to the number who perished. A good estimate as to the number of prisoners forced into the march is 75-80,000 combined U.S. and Philippine troops. Death estimates from the forced march and conditions at Camp O’Donnell range to as high as 20,000 soldiers.

The Monument

Fast forward to the 1990s in the city of Kissimmee, FL. In 1991, the city approved the project and dedicated a quarter acre plot at Monument Avenue and Lakeshore Boulevard for the erection of a memorial honoring those who served in the Philippines during World War II. The men who spearheaded the project were former Kissimmee City Commissioner Richard Herring and resident Menandro de Mesa who founded the Bataan-Corregidor Memorial Foundation. The Foundation set a goal of raising the roughly $125,000 needed for the creation and installation of the monument. The Osceola County Tourist Development Council contributed $10,000 toward the goal.

A Tribute to Courage
A Tribute to Courage

Sculptor Sandra Mueller Storm received the commission to create the haunting memorial. Storm is a renowned artist with multiple large commissions to her credit including “The Courage to Challenge” in Vierra, FL, “Called to Serve” in Hillsboro, KS, and “Melody of Arts” in Panama City, FL. Her work is featured in major collections throughout the country. In discussing her work she stated, “I think my major strength as a sculptor is the intensity of my involvement in what I create in bronze and the emotional impact my sculptures have on those who view them. Teaching sculpture for many years has also showed me how art can change lives, especially of children and the elderly.”

General Bruce Holloway who gave one of the speeches at the monument dedication. Photo courtesy U.S. Air Force

On Saturday, May 20, 1995, a day in which Florida spring rains would not hold off, the city unveiled the life sized bronze statue to a crowd of several hundred. The program included a wreath laying, and keynote speeches from Philippine Brigadier General Tagumpay Nanadiego and retired United States General Bruce Holloway.

The statue features three figures huddled together showing the pain and desperation of the march. The scene depicts a Filipina woman offering care and water to two soldiers, one Filipino and the other American.

Dedication Plaque
Dedication Plaque for the Bataan-Corregidor Memorial at Lakefront Park in Kissimmee, FL







The text of the dedication plaque reads:

This monument is dedicated to the Americans and Filipinos who served in defense of democracy in the Philippines during World War II, especially in Bataan and Corregidor and on the infamous death march.

Photos of the monument

A View of the Full Monument
Detail of the Pain Soldiers and Civilians Felt
Anguish on the Face of a Filipina Woman Providing Water to Philippine and U.S. Soldiers
Pained Soldiers Who Were on the Bataan Death March Receiving Water












American Caesar: Douglas MacArthur 1880-1964




For those wanting to learn more about the Philippines in World War II there are many excellent resources to consider. I recommend taking a look at these four titles.

Bataan Death March A Survivors Account
The Bataan Death March: Life and Death in the Philippines During World War II

Triumph in the Philippines







This post may contain affiliate links. If you click these links and make a purchase, I may receive a small commission. This commission does not affect any price that you pay. All views and opinions provided are my own and are never influenced by affiliate programs or sponsors providing products.

World War II

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Every student of World War II should subscribe to World War II. Written by experts and beautifully illustrated you will save each issue. Click the photo or the link to receive exclusive savings offers on this title and hundreds more. Your first issue will be in your mailbox before you know it.