I usually wait for the plant to tell me when to water. I know that sounds like a stupid answer, but it's true. Fall/winter growers usually start perking up right about now. It's also good to listen to your plant because I've had confused plants that are off seasons.

You just have to be careful that moisture is gone before you water again because it's cooler and I'm assuming your plants are inside during the winter since you're a zone 5b. As you're aware moisture doesn't evaporate as quickly inside.

Most of my cactus are winter dormant some still need water like my Melocactus, but most I completely stop watering till early March. They will get moisture from the air of course because everything is outside, but when it comes to me watering I give them nothing. Also my San Pedros, certain Opuntia, Ferocactus, and my Cereus repandus do really well in the winter rains. I just have to watch out for freezing temps, but where I'm at it rarely gets that low. Plus when it's raining it's always warmer:).

Here's an example of a fall/winter grower. I just started giving it water a couple weeks ago. He was a stick over the summer and just 2 weeks ago little leaves started coming out. So I watered and then this week I fertilized. So what I'm trying to say is it's always good to know where your plant's origin is, and to watch and let it tell you what it wants:).

Thanks! I'm just really nervous about over watering if the plants are dormant or underwatering if they're winter growers, I'll just be sure to pay attention to how they look and hope it all goes well!

Just depends on the plant, the pot (plastic, ceramic, clay?), the weather, the humidity, the potting mix--in addition to whether the plant is going dormant or starting to grow.

I'm learning just like you are, casual sweater, but I notice my Christmas cactus are growing, so I'm keeping them watered. The aeonium kiwis which have been sitting like dummies all summer should wake up, and I'll give them a little more water. I did a haworthia inspection this morning, and they look like they are growing a little, but I'm very stingy on the water for them since they are inside. I'm babbling, obviously don't know any more than you do, Casual, but you are on the right track to proceed with caution, observe your plants, and use the skewer trick. In my opinion, an underwatered plant will tell you it needs water, but once one starts to rot....you are done!

Also, in addition to the (very good) advice already given, it is important to note that a couple of mistake waterings out of season (or while dormant) will not kill a plant.

Many succulents are opportunistic growers. If you keep them indoors during winter and it is warm, they will keep growing - so watering should be ok. But do not forget the light. They could be kept in quite cooler conditions - if that's the case, they need very little, if any, watering. Did you see post by Harry (hablu) about his routine? He keeps them cool and doesn't water for few months. He says in - this thread - :

I slowdown watering right now and stop completely half/end october for most plants. First watering is say half march. So i keep them dormant during winter. The room I have them has a low temperature - say 10C. In dormant situation they don't (hardly) grow ; so the lack of light is not realy a problem