So eventually I’d love to be able to do my grocery shopping with my board, so I would love to see the various solutions you all out there have for this. Any available to buy products would be great too
This is the best one I’ve seen so far using a bicycle trailer.
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TKP Truck baseplate mounted over the rear truck on top of the deck. Old skate hanger cut in half and shaped so just one axle and the main bushing hole remains. bolt it on to the baseplate with bushings installed for that flexy movement. Use a length of 8mm booker rod and a socket connector to attach it to a deck with the front truck removed and a milk crate bolted to it and you have yourself a nice little beer carton trailer. I’ve got one but its being used by a friend who has lost his car license and needs to get his tools to work. Bit ghetto but does the job. Feel free to utilise this idea under the creative commons license agreement. any donations to me.
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See this is the kinda shit I want! Got any photos? I’m having a hard time picturing what this would look like
So I’m reading this and thinking “wow this is sounding like a good little hitch and trailer”. And you say milk crate and beer and I lost it lol. Great start, sloppy finish sir lol.
Honestly I’d trust a solution designed for beer more than anything else 
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I don’t have pics as its not here but I’m missing it tbh so I might make another one. If I do though i’d use flat aluminium and drill a 12mm hole in both ends and connect it to the truck on the board and a baseplate on the front truck position of the trailer. Much easier. Do not under any circumstance try to pull a double trucked skateboard. It will set off the worst speed wobbles you have ever had in your life.
That’s what I like to call, priorities lol.
why not just get a decent backpack?
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I’m thinking for like doing a big shop, or for taking a slab of beer home or something
Its less about being super practical and more just doing it because I can 
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In another topic i got idea about backpack with frame and wheels added to that frame…
Show me…
Maybe with better look and not so airplane luggage looking.
Clearance from ground should also be improved, so I would lean into camping style backpack with handmade wheel attachment
Something like this but with smaller wheels or another skateboard deck used as “platform”
http://www.packwheel.com/support/images/backpacking/packwheel-carrying-backpack-l.jpg