Assuming that your boat has the sloop rig without the sail track, the sail is not meant to be routinely raised or lowered, hence the difficulty in doing so. The clue is in the manual for the sailing rig upgrade kit:

Stainless track will allow you to raise and lower the mainsail with a halyard, instead of furling the sail around the mast like a Laser dinghy or traditional dory.

So out on the water, you're meant to wrap the sail around the mast to reduce sail area.

The ad copy also says:

Although you'll sail more slowly upwind, a convenient "first reef" is to take in the jib.

So if you want to do more convenient sail reduction, the upgrade kit is what you'll need.

Laszlo

   Understood, thanks for the information. How is one meant to wrap the sail around the mast in such a way that it is tight enough, without detaching the boom? I have rigging set up to raise the boom up paralell with the boom, but that still leaves a very loose sail, which I fear could catch enough wind in a storm situation to break the mast (this is exactly what happened with a previous sailboat I had, so I'm very hesitant about what I think you're describing).

Thanks again!

I don't have a dory so I'm not sure how it's done exactly for that boat, but on my dinghy with a sprit sail I get the same messy tophamper when I brail it, so I spiral wrap the brailing line around the mess that compacts it into a cleaner tighter form.

You could try something similar, with the line permanently attached to the top of the mast, running down the side and ready for use when you need it.

Laszlo

The Northeaster Dory is somewhat derivative of the Swampscot Alpha-Beachcomber dories of yore, and so is its sailing rig.  The Swampscot dory originated as a rowing boat for inshore fishing from beaches.  By the late 1800's, the type had developed into a recreational boat with a sailing rig intended mostly for racing.  The leg-o-mutton mainsails were laced to the masts without halyards, not meant to be raised or lowered in the normal sense.  When it was time to race, the mast with its sail was stepped, and the rig was set up and left standing until the racing was over.  No halyards, topping lifts, or lazyjacks were involved.

Reef?  Racers tended to eschew such nicities as reefing, going at it hammer and tongs for the finish line...or until the boat capsized or something broke.

This was all great for racing, but maybe not the thing for sensible daysailing, hence the upgrade kit to which Laszlo referred above.  Were it mine, I'd want that, and maybe a row or two of reef points as well.

.....Michael