Jennifer Osterling

Griffith-Cline Funeral and Cremation Services

Altogether<br/>4307 Vineland Road, Suite H-17-19, Orlando, FL 32811<br/>For more information, visit our website at <a href='www.altogetherfuneral.com'>www.altogetherfuneral.com</a><br/>Copyright © 2025 FPG Intermediate Holdco, LLC

Jennifer Ellen Osterling of Myakka City passed away suddenly and entered into Heaven and God’s unconditional love and light at the age of 50 on Sunday, January 9, 2022. Jennifer was born in Bradenton, Florida, December 15, 1971 to Lloyd Osterling and Gail (Melville) Osterling. 

Jennifer, also known by many as Jen, or Jen-O, had an utmost passion for horses and it started at a very young age and continued to grow over the years. She became an accomplished barrel racer and each year for twenty years Jen would ride one hundred and twenty miles cross-state from Bradenton to Fort Pierce on horseback for the annual historic Florida Cracker Trail Ride. She was the Trail Boss leader for ten of the twenty years. She had her daughter, Leah, in the saddle at one year old and Leah eventually accompanied her mother and one hundred other riders on the Cracker Trail and they would set up camp at night along the way. Jennifer loved listening to the stories and learning the history of the early settlers. 

Jen taught riding lessons at summer camp at the Char-O-Lot Ranch in Myakka, City, giving lessons to her daughter and young children that came from miles away to learn how to ride. She was devoted to and loved her work and it would always shine through in her beautiful smile. 

Jen worked as an experienced guide at C Ponies, leading people on rescued Drum and Gypsy Vanner horses in the ocean as the horses would swim in deep water. She was very knowledgeable and would explain the details and make sure you were at ease prior to the ride. There was always the excitement of seeing dolphins and she loved nature and being outdoors. 

Her passion excelled in the arena as she participated in the Cowboy Mounted Shooting with the Florida Peacemakers CMSA Club. Jen rode her beloved horse, Talkinmare. She wore a double gun holster and shot at targets while racing on her horse to break the fastest time with a clean shoot. She won numerous awards and she was proud of her collection of belt buckles for her many achievements. Other clubs and meets she was involved with were the Bay Area Bandits, Myakka Outlaws, and her special love of performing in the Gus Trent Rodeos that she talked so highly of. Jen also participated for her first time in the Cowboy Mounted Shooting Championship in September 2016, in Murfreesboro, at the Tennessee Miller Coliseum. 

Jen was heavily involved and devoted to her daughter Leah’s 4-H for twelve years and was involved in working on the Dakin Dairy Farms where she also became known as the “Milk Maid,” driving the milk truck throughout various Florida cities to help promote small businesses bringing milk in time of need during the onset of the Covid-19 pandemic. She would load up the truck with gallons of milk and even show her followers how to make butter. Jen was the hardest worker and she put her heart and soul in everything she did! 

Jen loved an adventure and at the age of eighteen her mother took her to Peru and down the Amazon River where they stayed at a jungle camp in the rainforest for ten days. She traded her shoes off her feet at a Jagua Indian camp and she learned their way of using blow guns to shoot prey for food. Jennifer got introduced to piranha fishing there. She later developed a passion for off shore fishing in the Gulf of Mexico and competed in annual fishing tournaments. She also loved snorkeling and diving for scallops with her daughter, family, and friends. 

Jen was a loving mother and daughter. Her legacy will live on in the hearts and minds of everyone she interacted with as well as those she reached but never met. 

Jennifer Ellen is survived by her daughter, Leah Dakin, of Myakka City; mother, Gail (Melville) Shumway of Sarasota; two nieces, Hayden and Ashlyn Shumway; stepfather, Erick H. Shumway; aunt, Marilyn Barrick; uncle, Warren Osterling; cousins, Jane (Barrick) Zimmerman and Paul Barrick; extended family, Christina “Shelly” Dakin and Erin (Dakin) Drake. She is also survived by so many close friends. 

She was preceded in death by her father, Lloyd Osterling; stepmother, Kris Osterling; brother, Erick David Shumway; aunt, Janet (Melville) Thurston; extended family, Farren Dakin and Levi Dakin. 

Visitation will take place at Griffith Cline Funeral Home, 720 Manatee Avenue West, Bradenton, on Wednesday, January 19, 2022 between 5:00 and 7:00 pm. 

Church Service at Parrish Methodist, 12180 U.S. 301, Parrish, Thursday, January 20, 2022 at 11:00 am. Graveside service after in the Parrish Cemetery, food and fellowship after graveside service at the pavilion at Methodist Church. 

In memory of Jennifer a fundraiser Go-Fund-Me has been set up by Lindsey Dakin for Leah, Jen’s daughter. Any support would be greatly appreciated.

https://www.gofundme.com/f/support-for-leah-dakin

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Jennifer Osterling Obituary | Altogether