PlacesSkip to the content

Chastain’s Restaurant

Chastain’s Restaurant closed its doors after 40 years in business on North Orange Blossom Trail in Orlando, on Tuesday, September 3, 1996, to the dismay of its many loyal and long-time customers.

An article in the Orlando Sentinel on September 7, 1996 entitled: “Chastain’s Regulars in a Stew – Eatery Closes – The Orange Blossom Trail Restaurant was an Orlando Fixture for 40 Years,” shares the shock some felt when they arrived in the parking lot to find the doors closed.

”It’s the end of an era. It’s the death of a generation,” said Tom Ramsey, a 30-year customer who arrived Friday to meet a friend for lunch. With its home-cooked meals, Chastain’s attracted people from all walks of life. Common laborers ate alongside office workers, politicians and sports celebrities. And the restaurant accommodated good crowds until the last meal – breakfast – was served Tuesday, Chastain said.”

Burrell Chastain moved his family to Orlando in 1948.  In 1953, Burrell opened his own restaurant at 7th Street and OBT, which he later sold to Maryland Fried Chicken. In 1956, he took over the restaurant that was to become an Orlando landmark – Chastain’s!

In the 1960’s, Chastain’s Restaurant was one of the most well-known places in Orlando. It was located on Highway 441 (Orange Blossom Trail), between Central and Washington, in a busy commercial area of Orlando about six blocks south of the intersection of two major routes through the city: Highway 441 and Colonial Drive (Highway 50) – probably one of the most heavily used intersections in Central Florida at that time.

Highways 441 and 50 were also heavily used by truckers, and Chastain’s Restaurant accommodated them with a large parking lot in the back for their 18 wheelers and traditional home cooked meals.

One of Florida’s big attractions was Gatorland, a few miles further south on 441 in Kissimmee, so tourists had to pass right by the prominent, well-lit restaurant. Many of them spent the night at the nearby Wigwam Village just down the street from the restaurant before enjoying an exciting day at Gatorland.

Growing up in the sixties, I thought Chastain’s Restaurant had been in Orlando forever, but Burrell and Helen Chastain moved to Central Florida from Indiana in 1948, and in 1956, they took over the former Arrowhead Restaurant at 23 North Orange Blossom Trail. That was the year after my family moved to the area from Alabama. At that location, the Chastains began a forty-three year Chastain’s Restaurant tradition. Burrell knew how to feed truckers, for he, himself, had been a truck driver before coming to Florida. The cuisine was American country-style cooking, and the menu hardly changed for 40 years. The Chastains developed a loyal local clientele, as well, with generous helpings and a friendly environment. Regulars ate there for decades, and they ordered from waitresses who worked there for decades and who knew all the regular customers by name.

Chastain’s Restaurant was open 24 hours and attracted a remarkable diversity of patrons. Burrell’s and Helen’s son Bill Chastain, who worked in the restaurant since he was a child, said, “During lunch, you’d be surprised who’s out there. State Attorneys, Attorney Generals, the sheriff, different judges, and the Harley-Davidson guys.”

In a February 23, 2003 Orlando Sentinel article,Chastain’s Helped Bring People Together – Customers Remember the Restaurant Fondly. The Orlando Landmark Closed in 1996 After 40 Years,” Jeff Kunerth described the same thing:

It had honey jars on every table, Formica tables and green vinyl booths, and Brenda Lee, Patti Page and Elvis on the jukebox…The menu was truck-stop fare — steak and eggs, hot biscuits, fried chicken, bottomless cups of coffee — but the clientele was cross-sectional Orlando. Politicians, policemen, clergy, businessmen, truck drivers, motorcyclists, secretaries, car dealers, athletes, salesmen, bankers.

Photo of two people looking at the menu at Chastain's Restaurant in 1962
Chastain’s Restaurant in 1962

Chastain’s became a community meeting place for locals. It was a place for eating, but also a place for discussion ranging from gossip to serious business and political planning. Chastain’s was a place where Central Florida residents of all walks of life rubbed elbows and got to know each other. In the 1970s, Black ministers joined the mix, meeting at Chastain’s for breakfast four or five days a week to discuss current events and civil rights issues.

Chastain’s had a number of specialties, but among the favorites was biscuits and honey. Honey dispensers were provided at every table. The general community filled the restaurant on Sundays and on holidays. Chastain’s had a traditional special for Thanksgiving, and on Easter, they colored hundreds of dozens of eggs to hide in the bushes for the kids to find.

The restaurant received several good reviews from Scott Joseph, and Lawson Lamar and the people at the courthouse were always saying good things about Chastain’s. The Chastain’s friendliness and connection to the community went beyond the restaurant environment and is illustrated by the 1960 incident of Hurricane Donna, the most devastating hurricane to hit Orlando before the multiple hurricanes of 2004. When the city lost power for several days, much of people’s food went bad. The food at Chastain’s Restaurant was protected by dry ice. Burrell Chastain activated his gas grill and served free food to 1,500 of his neighbors, including the police. This was the kind of people the Chastains were. Even though the food was free, the girls received great tips! The Chastains received many nice letters about the event, including one from Sheriff Dave Starr.

Another feature that added to the distinctiveness of the restaurant was the two-story lighted glass booth on the front parking lot. It contained the air conditioning unit for the restaurant, but also served as a performance venue. It was called the owls nest, and The 5 Owls, a country-western band, performed there. In a day before remote broadcast trucks, it was sometimes used for live radio broadcasts by disc jockeys from stations such as WFIV-AM (1080) and WHOO-AM (990), ballgames were broadcast from there on Friday nights, and it also served other purposes. One could sit in the parking lot and see the performers or DJs in the booth. Passing cars would honk at the DJs. Visitors could access the booth by a spiral staircase.

Bill Chastain worked in the main restaurant from the time it opened. He was 14. His first job was dip-out man at a steam table, and he also helped in the kitchen, peeled potatoes, and put up stock. As he got older, it became his responsibility to make the doughnuts, which he did every morning before attending Edgewater High School, and after school he made doughnuts as well. His father required fresh doughnuts. Bill rotated shifts with his father and mother, so that one of them would be present at all times during the 24 hour a day operation. Eventually, Bill took over the business after Burrell Chastain died in 1979. Helen died Sunday, February 4, 1990 at 73 after suffering a stroke. She worked in the restaurant until her death. By then, Bill lived in Windermere, and his sister, Judith, lived in Gainesville. The family had lived in Colonialtown until the late fifties.

Bill grew up in Orlando. In fact, he grew up at the restaurant! He was only six when his family moved from Indiana in 1948, and most of what he remembered from the old state was the snow and cold in the winter along with the heavy heat of summer. He attended Hillcrest Elementary in Orlando, then he went on to Howard Junior High and then to Edgewater High School when it opened. After high school, Bill attended Orlando Junior College. He was in the army active reserve for a short time around 1961. Bill’s sister Judith worked the restaurant in its early years, but she married and went in another direction. Bill’s wife and daughters were not interested in working in the restaurant at all, though the kids did work in the restaurant some.

The Last Days. Chastain’s remained a landmark even as Orlando changed around it. Disney, Universal, and Sea World replaced Gatorland as the main tourist destination, and Interstate 4 and toll-roads replaced Highways 441 and 50 as primary traffic arteries through town. Chastain’s began closing at 10 p.m. One thing that really hurt area was that downtown Orlando did not want to reach west of Division. Orange Blossom Trail (Highway 441) took on a new character. Regular commerce sprang up in newer parts of Orlando and dimmed on “The Trail”, which became known for drugs, nude bars, and prostitution. Chastain’s outside glass booth was boarded up because vandals kept throwing rocks at the glass. In the 1980s, Chastain’s Restaurant dropped dinner from its menu and changed its hours to 5:30-3 p.m.

Even as the area declined, Chastain’s saw its biggest days ever in 1981. The Rolling Stones played two concerts in the nearby Citrus Bowl, drawing 60,000 fans for each, and Chastain’s was packed! The 1994 World Cup games at the Citrus Bowl provided a similar boost. The five games between June 19 and July 4 averaged more than 61,000 fans. Chastain’s Restaurant was swarmed by the World Cup crowds, though some of the regulars understandably stayed away during the sixteen-day period.

The World Cup proved to be the last hurrah, however. By October local independent restaurateurs were reeling from news that another Orlando landmark, Gary’s Duck Inn, had closed its doors. This followed the closing in 1993 of two other local restaurants, Chris’s House of Beef and Gus’ Villa Rosa. Gus’ happened to be one of Bill Chastain’s favorite places to dine out. Remaining restaurant owners debated the future of independent restaurants in Central Florida. Bill Chastain remarked, “There’s just so much expense to staying in business that we didn’t have before. I think we’re just going to be extinct someday.”

For Chastain’s Restaurant, the situation was aggravated by a long period of road construction, through part of which the restaurant had no front parking space. In addition his daughters were not interested in going into the restaurant business, so Bill was alone. Bill became tired from the constant attention required by the restaurant; he could not even help his college daughters move into their dorms because he could not be away from the restaurant for more than an hour or so. With the area falling into decline, Bill decided he did not want to die on OBT (Orange Blossom Trail). Once he made the decision to close, it was only about two months before Chastain’s Restaurant served breakfast on Tuesday, September 3, 1996, its last meal, and joined Chris’s House of Beef, Gus’ Villa Rosa, and Gary’s Duck Inn in closing up shop.

On Saturday, September 21, Absolute Auctions handled the disposal of property and memorabilia. The land and building were sold immediately to investors who owned the U-Save Bargain Paneling and Plywood company next door, but they had no intention of expanding their own company. Instead, they hoped to re-sell it to someone who would re-open it as a restaurant, because they felt the area needed it. A barbeque restaurant showed some interest, but in the end the building sat there until it was torn down in January, 1998 to make room for a 14,000 square-foot Al’s Army Store Warehouse.

Bill Chastain closed the restaurant in 1996, but Chastain’s was such a landmark that, even after ten years, some residents who have no cause to pass through the old crossroads are unaware that it is no longer there.

Create Your Own Memento of Chastain’s Restaurant. When Chastain’s Restaurant was still open, an Orlando Sentinel reader named Joe Schmerler requested the recipe for the restaurant’s cornbread. The recipe was printed in the Sentinel on January 11, 1996.

Chastain’s Restaurant’s Corn Bread
Yield: 10 to 12 servings
3 cups of self-rising cornmeal
1 cup all-purpose flour
2 eggs, beaten
1 cup buttermilk
2 tablespoons sugar
Pinch of salt
1/4 cup Wesson oil

1. Heat oven to 375 F.
2. Mix together cornmeal, flour, sugar and salt. Stir in buttermilk and beaten eggs. Mix well.
3. Pour Wesson oil into deep 10-by-12-inch pan. Place baking pan in oven and heat.
4. Pour batter into heated pan and bake 15 to 20 minutes or until brown. Turn pan upside down to remove.

Contributed by – More Chastain information than anywhere else in the world!

William Russell “Bill” Chastain passed away January 30, 2012. View his obituary.

Back to top
TAGS: , , , , , , , , , , , , , ,

Chastain's Restaurant

No description has been added yet

Chastain's Restaurant

No description has been added yet

1962 Colonial High School Yearbook - Advertisements pg 207

Advertisements featured on page 207 of the 1962 Colonial High School yearbook include Chastain's Restaurant, Joe Edgar's Sinclair Service Station, Bro...

There are currently no audio related to this memory.
There are currently no video related to this memory.
There are currently no links related to this memory.
There are currently no documents related to this memory.

Comments to “Chastain’s Restaurant”

  1. Scott Brewer says:

    I’m one of those people the article mentioned. I’m astonished to find out this great old restaurant made it to 1996 before passing into Orlando history. In 1996, I had been married for 6 years! I would have loved taking my wife there. My fondest memory is the warm muffins brought out to drizzle with their honey…mmm.

    • Tim Shea says:

      I was stationed at McCoy Air Force Base from 1967 to 1971 after my discharge in February 1971 I started working for Hagood Brothers Marine on Church Street , all of us at Hagood Brothers used to dine at Chastain‘s probably two or three times a week for years. Tommy Hagood one of the owners of Hagood Marine used to buy our lunches. Us young’en used to eat Two Blue Plate Specials for lunch every time. Our table always included all the big wigs of Orlando – you name one and they’ve probably eaten with Tommy Hagood. Anyone that was rich enough to have a boat got it repaired at Hagood’s so Tommy was a friend with a lot of folks. Like a lot of the comments here Orlando went down hill after Mickey Mouse came to town. Back in the days before Disney Orlando was really a great place to live and work – now it’s just a memory like an Orange Grove gone and never coming back. I still live here in Casselberry but hate driving into Orlando and avoid it if at all possible. I think Progress sucks.

      • Kim P says:

        Greetings Tim! Thank you for visiting Orlando Memory and sharing the wonderful memories of dining at Chastain’s back in the 1960s-1970s. It was a special place, for sure! We hope you find other posts that bring back memories of happy times in old Orlando and continue to share your thoughts! THE ORLANDO MEMORY TEAM

    • Kim P says:

      Greetings Scott! Thank you for visiting and commenting on our post on Chastain’s Restaurant! That DJ broadcast booth had to make it one of the most identifiable restaurants in Orlando, at the time. If you have any photos of you and your wife at Chastain’s, we’d love to add a couple to the post. Just reply to this comment and we’ll get in tough. We hope you find more posts on Orlando Memory that bring back thoughts of happy time sin Orlando. THE ORLANDO MEMORY TEAM.

  2. Jeanette Davis says:

    I was born and raised in Orlando. My family’s favorite restaurant was Chastain’s. I got my engagement ring in the back parking lot before eating a celebratory supper there. Lots of good memories.

  3. James Hobbs says:

    I was born and raised in Orlando. My parents went to Chastains often. I always got there fried chicken. I never had a meal there I didn’t like. I wish that someone had some of the recipes they used to have. It was a great restaurant that I’ve always had great memories of.

    • Kim P says:

      Thanks for visiting and sharing your memories of Chastains. I never ate there but drove past on my way to work every day in the early 1970s. The thing I remember best is the radio studio in the parking lot!

  4. Patricia Johnson says:

    This is a great article but we’ve never heard of the 5 Owls performing in the glassed in location. They were known for performing at the Rainbow Ranch, a county and western nightclub. It was not Howard High but Orlando High School which later became Howard Junior High School (now Howard Middle School) after Boone and Edgewater opened. Also we cannot find any reference that says Valencia used to be Orlando Junior College. It was started as it’s own Junior College. Thank you for your great article and will appreciate if you find I am wrong.

    • Kim P says:

      Thanks so much for commenting on the Chastain’s Restaurant post. According to Mr. Chastain’s obituary, he attended Howard Junior High and Edgewater High School. According to newspaper articles and memories of Orlandoans like yourself, the elevated glass room in front of Chastain’s was used by radio stations broadcasting live from the parking lot. We have no additional information on the 5 Owls, but thanks for letting us know they performed at the Rainbow Ranch. We’d love to learn more about that business and other bands who performed there! You are correct about Orlando Junior College. It closed it’s doors shortly after Valencia Community College was formed and the campus became Lake Highland Preparatory School.

Leave a Comment