I have a truck toolbox that I keep a complete spare set of tools, sockets, wrenches, screwdrivers, hammer, prybar etc. Also tie down straps, a few rags, paper towels, chain, winch. And there's room to add things depending on what I'm towing/hauling. I also carry a battery impact and floor jack if towing a trailer.

 

I have a .50 cal ammo can in the toolbox in my truck. It has dogbone wrenches, SAE/Met sockets, ratchet/extensions, combo wrenches, allen keys, vice grips, channel locks, and screwdrivers. All of these are cheapo sales bin tools. This ammo can has gotten me or others out of too many jams to count.

I also have a 36" breaker bar, bottle jack, and a mess of recovery gear, shackles, and nylon straps for tie downs in there. Old 4/0 welding lead as well, have used it for jumper cables and some road side blob job repairs.

 

Recovery rope and a few soft shackles are imperative for snow travel. If using your receiver as a recovery point, a good shackle insert is necessary. Do not use a hitch and ball! Other than that, a basic mechanic set with ratchets, sockets, wrenches, pliers, hammer and pry bar should just about cover it. Don’t go fancy, these are “as needed tools” in a mobile environment so damage and loss are inevitable. I keep battery tools out till going on a trip since I have multiple vehicles and the batteries don’t like to sit, especially in the cold.

 

Knipex Plierswrench hasn’t been mentioned yet!
Think of any roadside or jobsite repair you may need to make and what tools you’d need to make them. Any spare parts you’d like to have along? Pins, clips, wire, tape, etc.
I’d keep separate boxes for the trailer and the tractor/attachments. My trailer box has tools to fix wiring, repack bearings, change a tire or light bulbs- things like that. It goes whenever one of the trailers are in tow.

 

I keep a couple of adjustable wrenches, pliers, screwdriver, fencing stuff, chain(s), ratchet straps, trailer spare tire, usually at least one chain saw, axe, shovel, jacks, gas and oil for the chainsaw, Woodsman Pal and some other stuff I don't remember at the moment.

Frequently I keep some cans of tree marking paint but that's a bit specialized. If they are in the truck, I'll also have a hatchet or draw knife for cleaning bark off before painting.

 

Small 12V air compressor, recovery strap (with seperate strap damper), hitch with ball, hitch with clevis ring, small shovel, first aid kit, two reflective vests, umbrella, two flashlights, a small socket set with 1/4" and 3/8" drive, a pair of fishing rods and light tackle, cigar cutters, cigar lighters(multiple of both), extra lighter butane, playing cards, plastic cheap poker chips and a few 600lb ratchet straps.

If towing I add: trailer "jack block" (a few pieces of 2x4 screwed together to drive one of the two trailer axles on to lift the other), a 1/2" battery impact with the correct sockets for the lugs, proper trailer straps for planned load and wheel chocks.

Mid October through early April: Boots, socks, pants and a sweatshirt - since I wear shorts and flip flops year round.

 

Most important might be your credit card will always take care of what you don't have ask me how I now !

 

My triple A card !

 

I don't go on the road but all our cars have this Vector 1600A Jump Starter in them.

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