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DSC01038 In mast raising with a roller furler connected to the mast the question arises; What do I do with the fuler while the mast is going up or coming down?   Well, you could have the Mate hold and guide it with the mast, or if you're by yourself, you can tie the furler luff off to the Gin Pole as seen in the picture.
DSC00423  For lack of a better term for his device, I've been calling it a mast yoke.   It's main purpose is to anchor the temporary stays (baby stays) to the pivot bridles on each side of the boat. The baby stays offer some lateral stability in raising or lowering the mast.  If you have a good roller reefing furler I recommend that you make up baby stays and pivot bridles if your boat is designed like this boat.  If your boat's cabin top is designed like a MacGregor, you would only need the mast yoke and the baby stays.

I firmly believe that this mast yoke would also work on an O'Day 25 or 26 in conjuntion with baby stays attached to the triangular plates, along with the boom bridles for over the bow mast raising.
DSC00628 The stern rail as mentioned previously is very helpful for supporting the mast crutch.  I favor this mast crutch set up because it allows you to mount your rudder on the stern at the ramp and launch your boat if you choose to raise your mast with the boat sitting at the dock.

Having a roller inside the crutch allows you to roll the mast aft or forward instead of having to man handle it as I was doing for many years.
DSC00627 In essence what we see in this pic is a Gin Pole with a small boat winch attached to it, pivot bridles, and the baby stays.    It takes a little time to set this mast raising rig up but we only do this a couple of times a year, as we both rent moorings at the yacht club.
DSC00428  When I first saw this guy raise his mast with a CDI Roller Furler connected to it one day at the club, I was completely blow away!  I've always wanted a good roller furler on my boat but there was no way that I could ever raise my mast with a furler connected to it the way I was doing it by hand.   This guy was a new YC member back then and I was later to find out that he had more clever ideas and mods than anyone I've ever known.  He used to categorize himself as a "tinkerer" and that he is to this very day.  I'm forever picking his brains and I'm still learning from him.
scan  The two most important things to remember when raising or lowering a mast on land or on the water is:  1. The wind direction.   The wind needs to be coming directly from the stern.  A wind from abeam will blow the mast over the side.
2.  The boat and/or the trailer needs to be level.  If the boat is leaning to one side, the mast is also going to lean to that side as soon as you raise it and it will inevitably go right over the side breaking the tabernacle in the process.
You need to remember that the stays will not prevent the mast from going over the side until the mast is all the way up.  The stays will then get tight and provide the stability needed.
This picture was taken at the Mattapoisett Ma. Boat ramp back in the 1990s.  My wife Dolores was sitting in our Delta 88 Olds reading a magazine.  I spend a lot of time out on the water and tan up real quick.   I very seldom get sunburned.
scan0002 To raise a mast on this boat from over the stern, I needed to build a mast crutch and attach it to my stern rail.  Fortunately my O'Day 222 came with a full stern rail which made it easy to attach a crutch to it.  I built the crutch out of some short 2x4s and some plywood.  It was adjustable in that it could be lowered to hold the mast in place while the boat was being trailered. I have another album on mast crutches on this site, so I won't elaborate any further on this except to say that this piece of equipment is very essential in mast raising.  
The main advantages of raising a mast from the stern are as follows:  The mast can sit in the crutches,( I have one on my bow pulpit also) with the track pointing down with all the stays connected, save the forestay which can be bungeed to the mast along with the topping lift.  No dirt ever gets in the mast track and the mast is always ready to go up as soon as you can untie it and roll it aft so you can pin the tabernacle.  It helps if you have installed a roller in the rear mast crutch.   I used to set the crutch to within arms reach and pin it into position.

The only other aid that is needed is a single sheave block which can be attached to the aft hole in the bow stem chainplate.  A 60'x 3/8" three strand nylon line is roved through the block and attached to the Jib shackle.  I spliced an eye to the end of the 3/8" nylon line for this purpose.
The Jib halyard is run up the top of the mast and cleated at the bottom.  The line will allow you to hold the mast in position after you get it all the way up.   All you need to do is take the line around the mast above the goose neck fitting so it doesn't slide down, and pull the slack out of it and tie it to one of your bow cleats.  This frees you up to remove the bungee holding the forestay and walk to the bow and attach it to the forward hole in the bow stem plate.   This picture was taken at a local ramp on a lake just down the road from where I live.

In closing I want to say that if you have an O'Day 22 or a 222 without a roller furler, this type of mast raising is the way to go but of course you could always build a Gin Pole and use it to raise your mast by either a small boat winch mounted on the pole or you could attach your boom vang to your bow stem plate and pull the mast up that way as I do.

Note*  If you plan on using your boom vang to pull your mast up on this boat or and O'Day 22, you'll need to replace the line with a long braid line of approximately 55' to be able to attain the reach in the blocks when the mast is laying horizontal and ready to go up.  
 
 I've found this to be the fastest and easiest way to raise a mast and it can be done in about 20 minutes.
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