1. Haven’t done it personally, but assuming you’re comfortable descending with the trailer, and the tree fits well enough on it, how bad could it be?  The tree itself isn’t really very heavy (usually)… Just make sure you have the correct tires for the conditions.  If it were me, I’d probably do it on my CX bike.

  2. Haven’t done it (yet) with a tree, but my heavy CSA share farm is 3 miles uphill from home, so it’s a blast to ride unloaded up there, put the food in the trailer (often included big heavy squash, gallons of cider, etc.) and roll back down the hill at a good clip.

  3. I have an old blue sky trailer I keep at work that you could use, if you want. Otherwise, it would be a good idea to tarp up so you don’t get sap all over your rig.

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