- December 4, 2025
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George and Anne Bailey purchased the community newspaper in 1970.
The last run of the old Winter Garden Times Cottrell press was managed by shop foreman John Halstead on controls and machinist Cy Hopkins catching the pages as they came off.
The Observer produces the West Orange Times & Observer and the Southwest Orange Observer each week, along with special sections including Season, Local Motion, Summer Fun, Friday Night Sights and Holiday Gift Guide.
Advertisers through the years have promoted everything from tools and machinery to restaurant specials to movies and real estate.
Advertisers through the years have promoted everything from tools and machinery to restaurant specials to movies and real estate.
The Winter Garden Times ran a photo of the first footprint on the moon in 1969.
Advertisers through the years have promoted everything from tools and machinery to restaurant specials to movies and real estate.
Advertisers through the years have promoted everything from tools and machinery to restaurant specials to movies and real estate.
Advertisers through the years have promoted everything from tools and machinery to restaurant specials to movies and real estate.
When Anne and George Bailey took over the newspaper, the office was located in downtown Winter Garden.
Sometimes newspapers promote themselves and the important role they play in the community.
The West Orange Times & Observer is printed using The Villages Daily-Sun’s state-of-the-art printing press.
The West Orange Times & Observer and Southwest Orange Observer staff is proud to be latest in a long line of reporters, editors, photographers, sales executives, designers and more to document the history of West Orange County.
One constant in the newspaper world is the content consistently is changing. Each week, we produce a 21-inch-by-12-inch publication, averaging 20 or 24 pages, that shares with readers — by way of articles, photos and advertisements — the local news, the latest decisions made by the elected officials in the area, feature stories on the people in our neighborhoods, school news, photos of local events, the offerings at area businesses and more. We produce multiple special sections, too, including Season, Local Motion, Summer Fun, Friday Night Sights and Holiday Gift Guide.
But no two weeks are the same in the West Orange Times and Observer and the Southwest Orange Observer. These newspapers are the product of working days, nights and weekends to capture the news as it happens. It is our responsibility to relay the information in a timely, effective and unbiased manner — documenting the lows and celebrating the highs.
When A.B. Newton started this newspaper 120 years ago — as the Winter Garden Ricochet — there’s no way he could have imagined his new project still would be going strong all these decades later. His four-page paper covering the news of the small place called Winter Garden now encompasses an area with about 174,000 residents that includes four municipalities — Winter Garden, Ocoee, Oakland and Windermere — unincorporated Orange County and the huge master-planned development of Horizon West with its five villages and a town center.
For 12 decades, this newspaper has been the only consistent local source for local news.
Our front pages traditionally are reserved for the biggest news of the week. In the 1940s, the newspaper covers typically had news relating to World War II, focusing on both international news and friends, relatives and neighbors being drafted to serve. The U.S. Army had a camp set up on North Dillard Street in Winter Garden, and after the war ended, that property became a frequent topic in the 1950s as local men fundraised for and built West Orange Memorial Hospital. The hospital became the focus in the 1990s when it was closed and the new state-of-the-art Health Central Hospital opened in Ocoee.
The construction and opening of Walt Disney World were covered almost weekly in the early 1970s, and the coverage continued for every new theme park opened by Disney and Universal Studios. Later that decade, there were big continuing stories of the murders at West Orange High School and the W.T. Zeigler Furniture Store.
We have kept an eye on the local citrus business, which helped shape West Orange County. The paper covered citrus count predictions, buyouts and several devastating freezes. And when the citrus groves were all but obliterated, reporters started writing about the many subdivisions and commercial developments taking their place.
High schools are a big part of our news, from classrooms to the performing arts arena to the sports fields. It was a big deal when Dr. Phillips High School opened in 1987, forcing friendships into rivalries between DP and West Orange High. The West Orange Times even created a rivalry football game between the Warriors and the Panthers called the Ole Orange Crate Game that continues today. The winner takes home an actual orange crate, and each year the scores are added to the side.
Lives were changed when an F3 tornado stormed through Winter Garden in 1998, killing three people and causing millions of dollars in damage. We were there to document the storm and its aftermath, including the strength of the community in coming together to help each other.
Years later, when three back-to-back hurricanes slammed West Orange County in 2004, we documented the damage and cleanup then too.
Perhaps the biggest challenge for the newspaper was when the COVID-19 coronavirus turned the world upside down and caused everything to shut down in 2020. We were faced with the dilemma of putting out a newspaper when there were no events and we couldn’t come face-to-face with anyone except our families. Like everyone else, our staff created home offices and held Zoom meetings, and we learned to pivot with our stories. We wrote about businesses closing and new online businesses starting, we shared stories of youth using their down time creatively and coming up with fun online videos, and we informed residents of the latest COVID news.
When organizations are chartered, we introduce members and the group’s mission. We have shared information about many Rotary and Lions clubs, women’s and men’s groups, Christian organizations, outdoors groups, scouts, veterans and more.
When businesses open, we have given readers information about the owners, their location and what they offer customers.
Without our advertisers, we couldn’t produce a newspaper, and all are important, whether they buy a one-time ad or engage in a years-long advertising campaign. It only takes a look back in our archives at the grocery store advertisements, vehicle lots and real estate listings to get a feel for the cost of living.
In 1954, broker Alma Johns listed a one-year-old three-bedroom house in Ocoee for $12,500, and Cappleman Agency was selling a three-bedroom home on a paved street in Winter Garden for $5,250. In the classified ads, a 1950 Tudor Champion Studebaker with leather upholstery and a radio was selling for $825. Piggly Wiggly advertised hams for 59 cents per pound, 10 frozen orange juice cans for 99 cents, two pounds of fancy plums for 29 cents and a 24-pack of Coca-Cola for 80 cents (plus bottle deposit).
In 1969, The A&P grocery store on South Dillard Street advertised hog jowls (tongue in, teeth out) for 35 cents per pound, a two-pound bag of long-grain rice for 29 cents, a one-pound can of Super-Right chili with beans for 29 cents and a one-pound can of Maxwell House Coffee for 69 cents. John Lamb Chevrolet was selling a 1965 two-door Mustang hardtop for $1,995 and a 1968 Chevy half-ton pickup truck for $1,795. For sale by owner: corner lot on hard road with a three-bedroom house and two-bedroom trailer with cabana, partly furnished with built-in oven and range, fruit trees, deep well and shallow well, located near the lake, $11,000.
In 1977, Jimmy’s Thriftway advertised Maxwell House Coffee in one-pound cans for $2.99, a 10-pound sack of white potatoes for 99 cents and six to eight pounds of Lykes smoked shoulder for 59 cents per pound. Norman Brothers Datsun was selling used vehicles, including a 1976 Pacer for $2,995, 1974 Duster for $1,995 and a 1975 Coupe DeVille in mandarin orange for $5,795. Wingard Land Co. Realtors listed a lakefront home on Lake Florence with pool for $39,800.
The first edition of Winter Garden’s first newspaper, the Winter Garden Ricochet, was published Sept. 13, 1905. The first editor was A.B. Newton. The Ricochet was started when Newton met a printer with the last name March on the train coming from Sanford. The printer was looking for work, so he and Newton struck a deal, March continued on the train to Winter Garden, and they put out a newspaper.
It contained four pages of three columns each. Subscriptions were priced at 15 cents for three months or 50 cents for one year, payable in advance.
A year later, Newton bought The Apopka Citizen and merged the papers, which he sold in 1909.
There continuously has been a community newspaper in the area since Newton established his publication 120 years ago. It has had a number of publishers and owners, and its name has changed frequently, but the Winter Garden paper’s goal has remained the same — to provide quality local content.
Following the Winter Garden Ricochet, it has been called The Winter Garden Times (around 1913-15), The Orange County Citizen (1918), West Orange Herald (early 1920s), Winter Garden Herald (mid-1920s), The Winter Garden Journal (1925-33), The Town Crier (1933-34), West Orange News (1934-48), The Winter Garden Times (1948-80), The Times (1980-87) and The West Orange Times (1987-2014) and West Orange Times & Observer (2014 to now). Today, two sister papers (including Southwest Orange Observer) deliver the news of West Orange County.
In 1926, the Winter Garden Herald announced that it was “now a corporation,” and “the newspaper plant has been taken over by a board of directors…to secure at least thirty of the leading Winter Garden business men who are interested in news of the better kind in this community and to show their support of a newspaper of this class by becoming stockholders in a small way.”
The oldest copy of the newspaper kept in the office archives is dated Dec. 1, 1932. The top headline of The Winter Garden Journal reads “Burch-Story to publish Journal.” Major A.E. Barnett of New York City, a former pastor of Oakland Presbyterian Church, was editor. The paper boasted new management, a new editor, new policies and new features.
The publication date was changed from Friday to Thursday to benefit the advertisers, who wanted the paper delivered in time for readers “to see their offerings before they do their weekend shopping.”
In 1933, Burch and his brother-in-law, William Story, who had formed the Burch-Story Press, started The Town Crier. This was distributed free.
Burch and Story changed the name to the West Orange News and charged $2 annually. After one month, they cut the subscription price to $1. The paper was distributed weekly “in the area between the intersection of the Gotha Road with the Orlando highway and slightly beyond the Lake County line, east and west; and between Fisherman’s Paradise and Windermere, north and south.…”
Lester Price Robinson was owner, publisher and editor of West Orange News, and working with him was R.S. Williams as editor and manager.
In 1948, Eldon Johns bought the paper and merged it with The Orange County Chief in Apopka. (The Apopka Chief later became a separate newspaper.) He changed the name from West Orange News to The Winter Garden Times. Ken Chatfield was editor.
In 1965, the owner of The Winter Haven News-Chief bought the newspaper but kept the name the same. From 1966-69, Don Barnes served as publisher and editor.
George and Anne Bailey purchased the newspaper from The Winter Haven News-Chief in July 1970. It was a true family business, as the Baileys and their four sons prepared the papers for mailing on their living room floor. It also was a small business: George Bailey could bring the entire issue home from the Winter Haven printer in the back of his small car.
The Baileys ran the paper from a small office at 18 N. Boyd St.
Many of Winter Garden’s teens worked for the paper on a weekly basis, handling the Tuesday evening operations once the paper returned from the press. The high-schoolers were responsible for labeling, folding and tying batches of newspapers to be loaded into a dolly cart and taken to the downtown post office for mail delivery.
In 1980, the newspaper office moved to 720 S. Dillard St.
The front page of the May 1, 1980, issue of The Winter Garden Times stated, “We’re About to Move!” The next week, they named Kenneth B. Morris managing editor.
Nearly seven years later, in March 1987, the Baileys changed the name again to better reflect the growing community, calling the newspaper The West Orange Times.
Mary Anne Swickerath was part of the staff for nearly 30 years, starting as an Ocoee reporter — riding her bicycle to the office to deliver the news she had collected — and retiring in 2009 as editor. Amy Quesinberry assumed the position of managing editor after Swickerath’s departure.
The paper was sold to Observer Media Group, owned by Matt and Lisa Walsh, in 2014. The company moved the office from Dillard Street to its current location in Winter Garden at 661 Garden Commerce Parkway, Suite 180, in 2018. Dawn Willis was named publisher. Later in the year, Michael Eng was named editor, and Quesinberry became the community editor. In 2019, Eng was named publisher and editor.
Through the years, as the newspaper name changed, so did the slogan underneath the name. Besides “In the Garden City in the Garden State,” it also proclaimed “Winter Garden, Florida — Where Money Grows on Trees,” “The World’s Largest Orange Shipping Center,” “Completely Covers the Rich Citrus and Truck Section of Western Orange County,” “Northern Gateway to Walt Disney’s World of Tomorrow” and “The Voice of West Orange.”
Newton produced those first Ricochet newspapers on a hand press with all the type set by hand. Less than a decade later, The Winter Garden Times used a big Cottrell press, with the shop foreman manning the controls while a machinist caught the pages as they came off the press. When this machine was retired, the newspaper was printed by photo offset, a method of printing, based on photolithography, in which the inked image is transferred from the metal plate to a rubber surface and then to the paper.
In the 1970s, the paper was produced with a number of electronics: typewriters, a Compugraphic machine for typing and printing copy, a headliner machine and a hot waxer. The back half of the office was filled with huge layout boards with large pages for the hands-on paste-up process.
After writing our stories on the desktop computers and formatting them to the exact column width and font size, we printed them, cut out the words, ran the paper strips through a sticky waxing machine and rolled them onto the pages.
Stories were written on Apple Macintosh computers and stored on floppy drives. Folks had to either mail to or drop off their photos and news at the newspaper office. We used film cameras and had photos processed in the darkroom.
It was a game-changer when the office got a fax machine and had access to email, and suddenly, the hustle and bustle of customers and clients walking through the front door diminished greatly. Technological advancements led to photographers using digital cameras and, today, smartphones can take superior-quality photos in some instances.
The newspaper went to an all-digital, server-based format in 2002; a website was created and served as another outlet for sharing our stories. When Observer Media Group bought the paper, the website was relaunched with a more powerful platform, and the staff embraced a variety of social media platforms, including Facebook, Instagram and Twitter (now X).
Today, everyone works on individual laptop computers and the page-creating process is done digitally. Many files exist in the cloud, allowing staffers to work from anywhere with an internet connection. After a hurricane knocked out power at our office and all our homes, some staffers worked from their cars parked near free Wi-Fi to upload their photos and stories. And, instead of driving the pages to the printer, today, we simply upload them.
Newton’s four-page newspaper covering the news of the area — and the area itself — certainly has grown. More folks moving to West Orange County meant more news to share. The first indication the paper’s coverage area was expanding was in 1933, when the name was changed to West Orange News. The name remained until 1948, when it was rebranded as a Winter Garden newspaper once again.
When the Baileys bought the publication, Walt Disney World was in its construction phase and West Orange County was about to see a major change in population, real estate, roads and schools.
Until then, the entire area boasted two public high schools (a third one closed during desegregation), two junior high/middle schools and six elementary schools. The real spike in schools came as Horizon West was developed, and today, West Orange County is home to eight public and charter high schools, 10 middle schools and nearly three dozen elementary schools, as well as multiple private schools from elementary to high school.
In 2015, the area was becoming too large for all the news to fit in one weekly newspaper, and the Observer split its coverage area into two papers. The West Orange Times & Observer concentrated on Winter Garden, Ocoee and Oakland; and the Windermere Observer (later renamed Southwest Orange Observer) covered Windermere, Dr. Phillips and Horizon West.
Through the years, the hometown newspaper has held onto a number of traditions, the longest being the annual recognition of local high school graduates. This annual tradition started in the 1960s with the inclusion of groups of photos of graduating seniors from Lakeview, Ocoee and Drew high schools.
It became a special pull-out section in the 1980s and has expanded to include class photos, a list of graduates, graduation information and a goodbye message from the principals.
The West Orange Times started its Reading Reindeer literacy project in 1998 to collect books for underserved children in West Orange County. The program will celebrate its 28th year in December.
The newspaper has long been dedicated to the students in West Orange County. For decades, a section, now called Observer School Zone, has been devoted to the area’s schools by highlighting students, teachers and events. When school is out, student writers contribute to the section, dubbed Summer School Zone.
One exciting tradition is bringing home awards for our hard work. Observer writers, photographers, page designers and ad creators regularly win awards in the Florida Press Association’s Better Weekly Newspaper contest.
These awards remind us that what we do matters. We present a window to the life of the community, and it’s our job to inform, educate and entertain our readers. We are constant. And we are there, camera and notepad in hand, to document our corner of the world.