The first attempt was in April with high water and fast current. Flipped the boat at the start and slunk home. Glad for the help from two strangers in a canoe.
Second attempt was in May and got a little further but it was too hard to paddle upstream with trees and branches down. Kept hitting the wood with the blade, couldn't keep going, didn't want to get out and drag the boat.
Ten days ago I saw five kayaks head up the Long Ditch and didn't see them come back, so I though I'd give it a try.
Last Saturday afternoon I put in at Millennium in Boston and went to the Ditch. Current was mild, water level was OK for the Chatham. Got under one tree by lying flat on the back deck and just pulling myself through. Just enough room, about a foot, between the tree and the water.
At the top of the Ditch (Needham Street bridge) there was fast water over rocks so I got out and waded and pulled the boat along for twenty feet or so to the other side of the bridge, then got back in. (Teva makes great neoprene boots!)
The rest of the trip was downstream, six or seven miles of meander, to get back to the starting point. It's one of the few places where you can do a loop like that with only a short upstream section.
Beautiful day, lots of birds and enough breeze that the bugs didn't land much. Saw only two other boats in two hours, both fishing with small electric motors. Very quiet.