This summer we spent a significant amount of time anchored in Cuttyhunk Pond, one of our favorite spots. We've been anchoring there for more than 40 years so I know it very well. The anchorage in the Pond has a reputation for being crowded and with poor holding, but we have found out over many years there is almost always room for one more boat!
The reputation for poor holding is well-deserved if you drop the hook in the wrong part of the Pond. Many areas are very grassy, to the point that some people can never get an anchor to hold. However, the main portion of the dredged basin, northeast of the mooring field, has good holding in mostly mud. We've rode out gales there and numerous thunderstorm gusts.
This post will not go into all the nuances of anchoring in Cuttyhunk, but instead is a collection of random thoughts collected while observing numerous boats anchoring in all weather. For further thoughts on Cuttyhunk anchoring just use the search function.
1. Lots of boats don't even consider anchoring in Cuttyhunk Pond. I see them every day circling around the mooring field searching for an available mooring. If the search fails they often head outside to search for a rental mooring in the outer anchorage. Many, if not most, of these boats sports a decent looking anchor on the bow that presumably is connected to a decent anchor rode, but they just don't want to use the gear. Is this because they perceive the anchorage as too crowded? Sometimes, but on other days I have observed this same behavior when I am the only boat at anchor. In our more than 40 years of visiting Cuttyhunk the only time I used a rental mooring is during Hurricane Bob, but I backed it up with multiple anchors on long rodes. Apparently anchoring is becoming something that people don't want to do.
2. I've carefully observed hundreds of other boats pulling or dropping anchors before and after dragging in a blow, and I can make the following observations about anchors. Without a doubt the new-gen anchors with rollbars perform the best and are least likely to drag. We've been using a Mantus since they first came out and it has never failed us. Danforth-type anchors and Fortresses seem to mostly be used by power boats these days, but once in awhile I see a sailboat using one. If they get it dug in and back down hard, no problem. But, sudden wind shifts often dislodge the Danforth-types. There are lots of CQR and Delta anchors still in use, and in calm weather they seem fine. Many survive big blows, but I have also seen a lot of draggers using them. If I see a Bruce or claw-type anchor going down I become very wary of that boat--lots of draggers use those. Various other anchors seem to have mixed performance. The other night a traditional schooner came in, casually threw a Spade anchor on all-nylon rode over the side, anchored in a bad spot close to the moorings, and then proceeded to ride out several blows that sent other boats dragging. On the other hand, I have noticed more than once Spades being pulled up by dragging boats, and inevitably the entire scoop is one big ball of mud and weeds.
3. The #1 problem I see every day is the use of too little anchor rode. Boats come in, let out some chain and sometimes line, then start to back down hard on what is obviously too short a scope--you can tell by the angle the rode makes as the boat slides backwards. Other times, they don't bother to back down at all. Even if you feel it is too crowded to lie to traditional (and safe) 5:1 scope I find that most anchors require at least that much to set properly. Once you've set the anchor hard with the engine, and there is no perceptible dragging, then you can shorten up to as little as 3:1 if you are using an all-chain rode. Just be prepared to let out more if the wind picks up, which it often does at 2am!
4. The #2 problem is dropping the hook in one of the weedy areas outside of the dredged square on the chart. This is done mostly by smaller power craft, but sometimes tried by big cruising cats too. It often takes multiple tries to dig down through the weed in those spots, and with each try the anchor comes up completely fouled with weed. People with power windlasses controlled from the cockpit sometimes have no idea why their anchor is dragging after multiple tries. Check your anchor visually if for some reason it doesn't hold! We have occasionally found upon inspection that we somehow fouled our own anchor with our anchor chain after spinning around and around it in light winds.
5. This last point has to do with these light winds likely to be encountered during lazy summer sailing. Sure, your anchor has been holding great on short scope for a few days, but consider resetting it if a big blow is predicted. This is particularly important if a dramatic wind shift will occur. An anchor that held well in light air from the southwest may not be well positioned to pivot and re-dig in when the 2am blast comes in from the northeast. You may also want to consider putting out a second anchor in these situations, but you have to be careful in a crowded anchorage not to limit your swinging in such a way that other boats on one anchor will swing into you. If when anchored in the prevailing wind your stern is close to the shallows, it is probably safe to consider putting out a second anchor on those shallows. When the wind swings around to come from the direction of the shallows you will stay in place while everyone else on single anchors moves away from you.