I'll pile on top of the wheel bearing comments. Jack, blocks, grease gun, get 'em serviced before the haul, verify or watch 'em do it. On 95 with trucks whizzing by is no place to have a trailer bearing/wheel breakdown especially north of DC...sh!thole of all roads.

Grease gun, brake fluid (if hydraulic brakes) ,ratchet straps. I have nursed a hot bearing 500 miles by pumping grease in it once an hour, had a brake fitting take a mystery sh!t on the way back from key west and roasted another bearing so bad that I had to jack and tie the axle up so I could get off the highway. Nothing like a 1000 mile tow, Good luck and take it slow.

I brought a buddy's 33 Donzi with less-than-stellar trailer home two years ago. In the parking lot we picked it up at, I serviced the trailer while he was in bank doing paperwork. We had asked everything to be greased and it wasn't touched haha. Tires were cupped badly, found a few loose lugnuts, tightened them. Found one bearing full of water and very rusty. Pumped that sucker full of Mobil 1 syn grease until rust quit coming out of hub, ran slightly warmer than rest and made it all the way home at 75 mph on highway with checks every time we stopped. Also pumped fresh grease into other 3 hubs until brand new tube of grease was empty. Topped off brake fluid but surge brakes were shot, darn glad I had Duramax with exhaust brake in Vermont hills. Cupped tires ended up shaking loose a fender bracket letting it flop around somewhere in Ohio, stole a couple non-critical bolts/nuts in parking lot to re-affix.

I packed cordless impacts, two spare tires with same hub pattern I borrowed, floor jack, grease, pancake air compressor, and all the tools necessary to change wheel bearings although didn't have spares packed since axle model was unknown at time.

Moral of story, take the hour to check everything when you pick it up, throw fresh "good" grease in hubs, air up tires, and roll. Pack loaded for bear and you tend to not have issues. Pack lightly and everything falls apart usually haha.

Bring every tool you think you may need to work on the trailer. When one of the wheels/tires comes rolling past you while you're going 70mph down the freeway you're going to wish you had them.

Every sellers trailer is "I'm good condition"...

Winter 2018 I sold my 32' Fountain to a guy from Rhode Island, we live in northern Michigan. When he asked about the trailers condition I said good but bring every tool he needed to repair a trailer. Who wouldn't with a unknown trailer.

Like everyone else said, new bearings, tires and brake system serviced to have a worry free trip. All those parts are always on the clock with trailering. If you don’t do them now, you’ll just be wondering in the furture. I had a guy come to the house and do my trailer quite reasonably (st pete beach)

Also, you’ll want a turbo diesel. There are gassers that can get the job done, but the range is terrible and stopping so frequently for fuel slows you down.

The only downside to the diesel is that they have so much torque, you won’t know when a trailer bearing is failing and turning to molten metal!

yea ,,agree on wheel bearings ....
i had the time being off work ,,so i decided to check my wheel bearings,,,had 4 bearing that were bad...no i dont trailer very far.

Thanks, all great ideas, I'll bring everything listed and hope for the best. I have AAA for the truck and Boat US unlimited towing for the trailer, I haven't used either and I hope I don't need them.

Don't forget spare light for the trailer and some wire butt connectors and electrical tape, and of course a work light/flashlight.

If it has surge brakes, I would make certain that it is properly lubricated so that it slides back and forth as it should. Hitting your brakes on the highway may be enough to engage your surge brakes, but sometimes a slow acceleration is not enough to release them if they are sticky at all. A dragging brake will heat up the drum/disc, spindle,bearing, and grease causing the grease to escape and then bearing failure. Has happened a couple of times to me.