There are many different mast raising systems used by trailer sailors. Some depend on modifications to the trailer and cannot be used on the water. Others use a gin pole as a lever. The system described here uses a gin pole (maybe that’s not the right term in this application) as a crane or gantry to lift rather than lever the mast. It remains stationary throughout the process; it does not lay down as the mast comes up.

It is a variation of a system sold by BlueWater Yachts for Macgregor boats.
http://shop.bwyachts.com/product-p/3418-1v0.htm

The pole is a 2 x 4, the winch is a brake winch from Northern Tool. I made the line going to the bow cleat a fixed length with an eye spliced in the end to speed set-up. The line from the winch to the mast attaches with a snap hook to a permanently mounted bale about 6’ up. This is also where the baby stays attach. The pole does not attach directly to the mast or step. It has a short cross pice as a foot and just wedges in place at the foot of the mast. Friction holds it in place. I have never had a problem with this or felt the need for a more positive connection after many years of doing it this way on several boats.

The baby stays do not have much load on them, they are there to keep the mast centered. I initially used a strop around the grab rails as the deck attachment point. This worked ok but then I realized that the forward fasteners of the deck organizers were right in line with the mast. I replaced the forward fasteners with eye bolts and put snap fasteners on the bottoms of the baby stays.

I also added a pair of baby stays to the gin pole itself. These are not absolutely necessary but make life a little easier by keeping the pole upright while I set up the rest of the system. To further speed setup I spliced the bottom ends of these stays to the same snap hooks that terminate the mast baby stays.