Comment a list with years and pictures if you can.  Oldest ones I know that are still standing:

Augusta, Carr Creek, Wayland, Germantown, Maysville

Owsley County’s old gym was built during the Roosevelt era by the WPA. Opened 1938. It was re-floored and renovated about 3 years ago with new windows, paint job, scoreboard, etc. It is one of the small floor styles that many called “Cracker Jack boxes” back in the day. Exterior is sandstone cut from the South Fork of the Kentucky River that runs from Clay County through Owsley County and on to Beattyville in Lee County. There it meets the Middle Fork and North Fork of the Kentucky to form the Kentucky River. 
 

(The last part of the post has nothing to do with old gyms but I can’t resist giving a little history/geography about where I live).  ?

Alvaton High’s gym is still around. They’re about to renovate it again to restore its look and to get it more functional for events. It was built in 1942. 

The book Legacies of Kentucky Mountain Basketball by Harold Kelly, published about 10 years ago, identified a lot of old gyms still standing at that time.  Last time I checked, the gym at Cuba in Western Kentucky was still standing but not in very good shape.  

Augusta’s gym, affectionately known as the “Panther’s Den,”  is still in great shape and very much in use. The gym was built in 1926 and has undergone many renovations to keep it up to date over the years. By the time the gym reaches 100 years the Panthers plan on hosting the 39th district tournament in their new gym that is expected to seat 1,000 fans and sit to the east of the current gym on Augusta’s cozy little campus in the center of town. The current gym has hosted many different events over the years and will still be a very vital part of the school and community for years to come. So if you’re a fan of the old school cracker box gyms this is certainly one to see. It’ll take you back in time. 
     I’ve included a video of a game vs. Bracken County from February 13, 2016. It was shot from the stage and has a great view of all the seating available. Fun fact, this was the last time Augusta and Bracken County met in the regular season until December 6, 2019 also at Augusta, when fans lined up hours before to get in to see that one. I have a video of that as well but this one has a better view. 

1 hour ago, Quagmire said:

I’ve included a video of a game vs. Bracken County from February 13, 2016. It was shot from the stage and has a great view of all the seating available. Fun fact, this was the last time Augusta and Bracken County met in the regular season until December 6, 2019 also at Augusta, when fans lined up hours before to get in to see that one. I have a video of that as well but this one has a better view. 

I was there that night. Sat in the balcony above the bench; never saw either coach or bench from my view. One of the best high school basketball viewing experiences of my life.

Hazel Green (Bullfrogs) in London have their old gym that was built in 1937. They won a state basketball championship in 1940. 
It’s really nice. Has been renovated a few times and well kept. The adjacent buildings and gym are part of Laurel County’s elementary school system nowadays. 

Hazard’s Memorial Gym has been standing for a really long time, not sure how old it is.

Sadieville High School in Scott County was built circa 1920. The first ball team played in 1922. The gym (and school) is still standing but just barely. 

4 hours ago, nikeman49 said:

Hazard’s Memorial Gym has been standing for a really long time, not sure how old it is.

Opened in 1950 and named in memory of the Perry County servicemen who died in WW2. 
They have it looking pretty good for a 72 year old facility. The new lights they have installed are a huge help because it had always seemed to be poor lighting in the past. The new ones must be LED. The floor looks great and the interior has been painted.

There’s a lot of history inside Memorial. 

15 hours ago, The Professor said:

Opened in 1950 and named in memory of the Perry County servicemen who died in WW2. 
They have it looking pretty good for a 72 year old facility. The new lights they have installed are a huge help because it had always seemed to be poor lighting in the past. The new ones must be LED. The floor looks great and the interior has been painted.

There’s a lot of history inside Memorial. 

Attended my first game at Hazard's Memorial Gym during this year's 54th district tournament.  Hazard v. Buckhorn.  Enjoyed the gym and the game very much.

Somerset is a very nice, old gym in my part of the state. It was the almost annual host of the 12th Region tournament from the 1930s through the early 1960s. They did a major renovation several years back and it looks even better now than before. Great place to watch basketball.

8 hours ago, gchs_uk9 said:

Somerset is a very nice, old gym in my part of the state. It was the almost annual host of the 12th Region tournament from the 1930s through the early 1960s. They did a major renovation several years back and it looks even better now than before. Great place to watch basketball.

Photo Credit: George Rogers Clark Girls Basketball @grchoops

On 3/14/2022 at 10:19 AM, The Professor said:

Hazel Green (Bullfrogs) in London have their old gym that was built in 1937. They won a state basketball championship in 1940. 
It’s really nice. Has been renovated a few times and well kept. The adjacent buildings and gym are part of Laurel County’s elementary school system nowadays. 

Photo Credit: Coach Brad Sizemore @headcoachbrad

A few years ago I saw a gym in the building across from the current Holmes gym. I would guess that old gym was the original high school gym. I believe the building was built in the 1920's. Is that gym still used as a gym?

(Side note - in looking for info on this a wiki note said Holmes is the oldest public high school in KY, founded in 1853 as Covington Central. Is that correct?)