I just recently purchased a 96 challenger bass boat. I am having trouble trailering it for some reason. This is not my first boat so I have some experience. When trailering this boat I cannot get the bow of my boat to clear the bow stop. I trim my motor up and I have tried different levels of how far down into the water I back the trailer. I don't have a problem winching it up some but I fish be myself a whole lot and when I have to winch it up some I can't lift up on the front of the boat and turn the winch at the same time to clear the bow stop. Any suggestions.

sounds like you're backin in too far

+1 on down to far.

Note where your trailer is when the back end of your boat starts to float when backing in to unload. Then when you load put the trailer in about 3-4 inches more out of the water and power onto the trailer.

To deep on the trailer. That boat will slide right up.

Either you are indeed backing in too deep or your bow roller post has moved. Also, it's possible that the bunks on your trailer are not at the proper height. Check to see if they have adjustment holes.

Ditto. Definately backing it in too far.

I had a similar problem and come to find out it was that my bow roller post had evidently been hit at some point and it moved it forward about two inches. I moved it back to where it needed to be and really gave it a good tightening and haven't had a problem since.

I have the same problem with my ski boat...it doesn't have the bow rollers, but has the V shaped "bow stop" which is higher and further up on the trailer.

If you back in far enough so that the bow of the boat goes above the bow stop then the boat is still floating above the bunks of the trailer.

If you only back it in where you can pull the boat onto the bunks, the bow stop is several inches higher than the bow, so you have to physically lift the front of the boat while you winch it up. Which is difficult to do if you're alone.

If you try to drive it up on the bunks, the bow stop comes in over the top of your bow (and in my case would knock off the front light).

What I end up doing is backing in so that I can drive the boat up the bunks about 3/4 of the way to the bow stop, and hooking to the boat with the winch. Then back the truck up a bit more so that the bow stop is low enough that I can winch the boat up over it.

Although, I'm going to take Kat-Man_do's advice and check out the height of the bunks and see if they can be adjusted. I think that would solve my problem. Sorry to highjack your thread, just wanted you to know you're not alone.

Another suggestion. I most often fish by myself,too.A couple of years ago , I replaced original winch with a much heavier one(from Bas Pro) and I can winch my 19 ft. boat on any ramp. Just a thought.

Here was my solution to the problem. I'm 63 years old and I have major-league heart problems. Like you, I usually fish alone. When things don't go perfectly, I've got problems. Depending on the situation, there's absolutely no way for me to winch the boat up without assistance.
The trailering problem was always there, but when I added a keel guard all hell broke loose. Adding a keel guard doesn't seem like much of a modification, just 3/8" or so added to the width of the keel, but I could see marks where the keel guard was contacting the inner bunks improperly. I replaced the inner bunks leaving a wider distance between them and applied Liquid Rollers to all the bunks. Now my boat idles up to within one foot of the bow stop and finishing the job with a winch is almost effortless. Liquid Rollers is a pain in the a%%--the bunk must be dry before application and the Liquid Rollers must dry before use--but it beats hell out of a heart attack or tying up a boat ramp that other folks need.
As far as the advice that your trailer is too deep, now that the above work has been done, I back my trailer until the tops of the fenders are about 5" above water.
Hope this helps.

My guess is this is a roller trailer I recently aquired my first roller trailer (which i hate btw No loading piece of junk) With a roller you dont back it in the water near as far I have loaded on this trailer hundereds of times now and still have to be very careful loading or it will be crooked I refuse to winch it on but it will be straight every time if i do and actually a roller trailer is meant to be winched on vs driven, Im thinking about moving my rear guides tight against the boat and see if that helps as many tempers flair when it comes to no loaders at the boat ramp I know it really yanks my chain when somebody screws around winching a boat on rather then driving!!!!

try adjusting the winch and bow stop.