You'll need either more than 1 tree of a different variety or a tree with multiple varieties grafted to it, to get fruit.

You could get a 1 single variety tree then top work the tree 1/2 way up to get a 2nd variety.

I'd recommend:

Wolf River
Calville Blanc d'Hiver
Reine des Reinettes

Those are all Diploids, and have viable pollen and can pollinate each other. Great cooking apples.

They'd have the space for additional trees if that would be the better way to go. Could do 2 or 3.

Are the ones you listed widely available?

I've just about finished my first crop of Sweet Sixteen (3rd year tree) and have been very happy with it as an early mid-season apple. They are crisp/crunchy (though not as hard as some other apples) and sweet, with a very interesting flavor. I'm not sure how it is for cooking, but it makes a very good eating apple. It was released by UofMin, so it should do well in your area.

If you are just starting out, I wouldn't recommend grafting right away, but it is fun, so keep it in mind for the future. You can find Sweet Sixteen at ACN, Cummins, or GrandpasOrchard, all of which should give you a good tree.

I haven't done any cooking with apples, so all I can suggest here is checking online. For example, WSU has a page with some suggestions. Of the ones which they consider good cookers, Grimes Golden and Roxbury Russet should be among the easier trees to grow and available online.

I would suggest going to local orchards and try as many different varieties as possible because different apples taste different from different areas. If I had to pick just one apple for baking in WI I would choose Cortland

Yes, Cortlands are great baking apples for Wisconsin, and good fresh, too. You have to leave them mellow a week or two after picking for great fresh eating. Northwoodswis

zaphod:

My home orchard of 20 assorted fruit trees is in washington county!

We can grow a lot of apple varieties here provided they
ripen by October 15th. Anything later than that is taking a chance.

Cooking apples? I agree with Cortland as it is a large apple and dual purpose (cooking and eating). The bad news is that it is very prone to apple scab although the damage is cosmetic and will not be an issue with the flesh.

I enjoy cooking with jonathan, cortland, Mcintosh, NW greening ect. My favorite pie apple is Regent. My favorite apple for sauce is McIntosh. My favorite for strudel is McIntosh or Cortland.

I would say that their are many great cooking apple varieties that will grow here depending on which ones you like. You can stop out at Barthel Fruit Farm in neighboring Ozaukee county and sample what Bob Barthel grows. He has an amazIng orchard of u-pick and
pre-picked if you need ideas. One of his favorites for cooking is 20 ounce. A very large fruited apple.

Whatever you plant, buy from a reputable source that tells you what the rootstock is. Avoid our local chain stores as they cannot tell you the rootstock. Very important to know so you can space the trees properly.

For the most part, apples need to be cross-pollinated so you will need to plant 2 different varieties unless you have a crabapple nearby to use for a pollinator.

I think you can do a lot better than Cortland and McIntosh.
Both are subpar.
If you want to plant a McIntosh type apple, I recommend Jonamac. Taste and ease of growing is superior to either of its parents.

Cortlands to me are the mainstream pick-your-own variety for cooking.

I still feel the ones I mentioned above will do well where you are and will offer more than Mac or Cortland ever will. This is coming from someone is 5a - NY, Mac and Cortland capital of the world. I've had products of cooking with them both, and they fall flat IMO.

Belle de Boskoop is a real strudel apple, once you have a traditional strudel with that variety, you will see more clearly which is far superior.

BdB doesnt apply here, as its a Triploid. It would require 3 trees, 2 other being diploid, and early flowering to pull it off, but worth the effort.

I have Cortland and McIntosh and i rarely even spray them. They get a lot of leaf issues...the fruit can look a little rough, but the Cortlands get huge and i still get plenty to eat (even after the birds/squirrels). Out of the 2, i'd probably take the Cortland, but to me they seem pretty similar, other then size. Now compared to the Honeycrisp, they look great! I'm probably going to graft over the Mac and remove that tree (not the greatest spot).