What you need is a small, extremely simple mining car set-up, so look at how-to mining literature. Historical stuff should be loaded with calculations you might need to consider. Another good place to start would be to look at roller coaster lifts, and the like, along with diy backyard roller coasters that people have built. I would think you are mostly limited by your available skills and budget. If you can weld, and are fairly mechanically inclined, this should be a piece of cake. There are no-weld options as well. Steel is damn pricey these days, at least it is in my parts, so without some source of surplus materials, it might not be worth it. That is, not until you need it one day, and don't have it! Lol good luck!

I rented a house in New York on a lake during Christmas of 2021. The house set well below the road, with lots of steps. They had a pulley system with a small crate attached that went to the house. A pulley at the house and a pulley at the parking area, with a second rope on the crate. You would load the crate and gravity would let it travel to the porch. We had to kind of hold the rope to keep it slow. Someone would empty, then pull it back up, and load again. After the first load, we just decided to carry our stuff down. It was pretty worn and not all that smooth. We didn’t want to chance having our stuff fall into the shrubs and rocks with lots of snow. It was mounted to a 3” steel post at the top, and bolted to the house wall at the bottom. It must have been a pain in the ass to install and tension everything.

some of the old L shaped iron rails on wooden tracks that were used well into the 1800's in mines (because they're light..) wouldn't be that hard to reproduce for a straight run.. Combined with an electric winch set on a deadman at the top (inside a covered cart stop..) and you'd have a pretty cool system.

ATV winch with remote, and a garden cart.

I built a hoist "mono trolley in my garage. I used 2 x 6 on edge with a strip of steel on the top. I used a solid wheel from a HD store caster. It works great for me, perhaps a variation might be useful for your project.

Also note in our state we have a company that sells steel commercially. They have a large out building with "scraps" (some are really big scraps). Perhaps there is one in your area.

Any type of 12-volt winch should work just fine - 60 feet isn’t that far, and you’re well within the weight limit of the cheapest winch. (Even a half ton winch could safely lift 330 pounds.)

For your trolley, I’d look at making “rails” from L-channel steel. Put the vertical piece in the outside. The cart can just be a square of steel with some roller skate wheels on it. They tend to have good bearings and are fairly durable.

The advantage I see using the L-channel is that you can go over whatever your existing landscaping is - you could have flowers, grass, etc. in the middle, and the cart should mostly just push them out of the way.

Google ‘inclinator’ and check out the pics.

Spent time at a camp a few years ago and this was the access and from the lake.

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