Can f-150 tow Winnebago One dry wt. 6580?

Nope! Not even close. A PuP is about all you could pull with that. For the trailer you have in mind you need a newer properly equipped 1/2ton, but sonce you would have to buy something I would buy a 3/4 ton and be done.

I beat a 97 or 98 triton v6 5 speed truck from NM to WY and back for about a year. Construction duty during the week.
Tough little truck, but that screamin 6 ran out of breath pretty quick.

Considering your truck to be in great shape still at its age, the combo of low power and being almost 20 years old is not an awesome combo for what you're looking to do. And your clutch won't love a big trailer. Trucks not geared for pulling.

2 thumbs down. Not from the chassis standpoint rather the age and power train combo.

Don't do it. That's too much trailer for that truck when it was new. Now your truck is 17 years old. You'll kill it.

welcome to the forum.
Looking at Fords '99 specs show your F150 V6 truck can may have a:
...5000-6000 GVWR
...2000-3600 lb tow rating (manual tranny)
...4800-5500 lb tow rating (auto tranny)
...small 3550 lb rear axle weight rating (RAWR)
All depending on gear ratio selections and cab selections your particular truck has.

A 6580 lb trailer may weigh in the 7500-8000 lb range when road ready.
Your going to need a newer gen F150 3.5 ecoboost or 5.0 engine with a 7000-7750 GVWR and 4500-4800 RAWR packages
OR
a much smaller trailer. Good luck

I think you are in MN but was going to suggest to head down to Arkansas and drive the two lanes section of US82 between Lake Village, AR and Crossett, AR where the Georgia-Pacific wood plant is located and see how you can perform meeting up with one of those logging trucks going 75MPH. They are loaded down with hugh pine trees stacked to 13-feet height. The last thing you see is the smile on the drivers face and its Katie bar the door after that... The hugh wind draft would knock my ham radio antennas off my truck haha...

Even my 4200lb loaded POPUP trailer in its towing mode neatly hid behind my truck wind wake would go all squirmy. Hard to stay on the roadway... Can't imagine what a larger trailer with high hard sides would perform there...

Have to pry your fingers off the steering wheel after all of this haha...

Roy Ken

The short answer is no. The long answer is that you have not posted enough info for anyone to give you a complete answer. Take my word for it a 20 year old 6CYL will not tow a 7500 (ready to roll) Trailer. Do the math.

That trailer is going to be close to 8k when loaded. Towing that with an old V6? No way. That's pushing the limits of new 1/2 ton trucks.

The dry weight isn't the camping weight, and that's a 32' trailer. I'd hesitate to pull it with any half ton, let alone a 15+ year old model with a V6.

also, what part of the country are you in? Towing conditions mostly flatlands, rolling hills, mountains? All could end up in "somewhat do-able" to "ain't gonna work" ...

Bigger question - maybe it could tow it, but can it stop it?

Our '97 F150 had a V8 and a tow package. I would move our TT (about the same size as yours) but it did not like it. It would be in 2nd a lot on the highway. I think it would be a good way to kill your truck.