OP, with this new information, that is a BIG trailer. Have you ever driven a semi truck? 50ft is a common length for semi trailers, then add on the length of your pulling vehicle, for a total length you will have to manage. So you need to start thinking like a semi truck driver in how to manage your combination.
We have such a truck and trailer of 53ft, for a total over 60ft long. I have to say it can be a bear getting in and out of a showground, on wet or soft ground. You usually cannot park close to barns, you are too big. It is very easy to get parked in, can’t leave when you want. VERY frustrating! You cannot stop for food “just any old place”, you have to consider your size with every move you make. Location of trailer axles will control your turning radius, with axles closer to the rear shortening the turns. Trailer will turn way inside the tracks the pulling vehicle made! Our outfit makes 4 seperate tire tracks doing a 90* turn, and tracks may not be close to each other!
I am going to say for a 50ft trailer, you will need a CDL-A liscense and may need the air brake endorsement, to be legal. Both our 35ft Featherlite with the heavy axles, big tires, and the semi trailer have air brakes. I feel very confident in being able to stop when I use the brakes. My State goes by both weight, over 10,000 lbs, AND length, in requiring the CDL licensing to drive bigger trailers. Yes there are folks driving without a CDL, but I sure would not want to be one if pulled over or in an accident. Fines can really add up.
I am SURE you can drive such a rig with some instruction and practice. Then pass the driver testing. Getting proper instruction will make things easier for you, start resetting your thinking to be a truck driver, in doing things safely and correctly with this big rig. Getting the truck driver manual from your Sec of State office will cover lots of what you need to know, details. Do know that the information in testing covers ALL kinds of semi truck drivers, so anyone liscensed with a CDL can drive any kind of big truck outfit.
You will need a bigger truck/truck-tractor to pull the big trailer. Figure what trailer will weigh fully loaded, in considering size of pulling vehicle you will need. Tractor vehicle needs enough power to manage the full load in hills or mountains without losing much speed. Trucks come in automatic and manual transmissions these days, so if you are not familiar with shifting a manual, you have another option. We pull the Featherlite trailer with a 2-ton truck that has a flatbed. The semi trailer has a semi tractor to pull it, enough power to easily manage the fully loaded trailer wherever we go.
I have a CDL-A with the air-brake endorsement for work, drove professionally, so I was “prepared” when we changed to the bigger trailers. We had other women driving for the Company, so you should be confident in being able to manage such an outfit. Not trying to “talk down” to you, but at times dealing with men drivers can be very discouraging. In fact the women drivers had better safety records!
With friends who like to show, I seriously suggest going back over your trailer plans to see if you can reduce the length. They went with big trailers and find them difficult to drive and park at shows. Many sold them after short times, got smaller trailers that were easier to manage. Widths were a big issue for them, in trying to keep 8ft wide and long lengths between the lines on long hauls. No room for error in correcting your travel like a smaller width trailer gives you!