some pics of the whole tree would be helpful in overall advise. I'll let someone with more pear experience advise on the subtle signs of best time to pick. But will add if not certain you are picking at the right time don't pick them all. keep dated notes and you can figure it out so you hit it right on in the future.

I'm not a pear expert, and I'm not sure if someone can identify them by their pictures, but I second the 'keeping a journal', you may be able to zero in on the variety by noting the bloom time, and susceptibility to fire blight, etc. I'm in Georgia and there's a handful of 'common' varieties that are blight resistant, the others get beaten up pretty bad. If it's fire blight resistant, productive and the pears taste good, sign me up for cuttings!

Good luck.

Here are some pictures of the tree as requested. Some of my questions are

I have noticed that my pears only seem to be growing on the north side of the tree....is there a reason for this? Just the most optimal sunlight maybe?

another pic...

..last pic

You have a beautiful tree but the thickness of the limbs/foliage does not permit light to get to many areas of the tree. I would thin out some of the limbs and gradually open it up. Google pear pruning and proceed slowly if you new at this. I cant tell you the variety of pear it is, but I'm sure it is not the Orient variety.

I would wait until late winter to do any pruning. Also to be sure we are looking at the larger tree in the first pic, not the one that looks bush like at the ground, correct?

the north side producing may be pollen source related. You could graft a couple other species onto this tree to get good pollen in the future. Bartlett likes to pollinate lots of other pears, so I would add it as one. Don't try to mix Asian pears on the same tree. Also do more then one of each. Even if you graft well there are birds, squirrels, kids etc to knock it off before it is solid. you would do this in the spring

So on pruning start looking at it after the leaves fall. You have a lot of branches overlapping each other. You will want to pick some of the best branches and mark as keepers then see what that leaves in regards to branches to remove. IN removing branches most will be cut away at the trunk. But some will be removing one leg of a Y.

So grafting and pruning are both done early next year. you have time to get your mind around it. Also on things like this you can make it a group project and post photos and bounce ideas off the rest of us. You will get a mix of ideas because that is how these things go. But as you learn you will develop the style that appeals to you.

I agree. Your tree needs a good pruning and the density of the tree might reflect the north side fruiting. From the pictures, the fruit resembles that of Kieffer, which is a very common pear and usually FB resistant, and requires very minimal care. Most Kieffers' grow well on their own, as is evidenced by your tree. But I think you would find the tree to be more manageable and more productive, if you lowered the tree and pruned out the center leader and use the open vase system. I do this to all of my pear trees, so I don't have to get on a ladder to harvest them, and I get much more fruit.

"From the pictures, the fruit resembles that of Kieffer, which is a very common pear and usually FB resistant." - rayrose

I was thinking kieffer or bartlett.

When my parents bought their land 30+ years ago, it had a full size pear tree (on its own roots) growing along a farm field. I thought it was most likely a kieffer, but the old timer next door said he had some along his fields too and they were bartlett. This tree is huge and very vertical. It is at least 40' tall with a 24" trunk. There are 3 scaffolds about 10" diameter. Many times I stood in the field and wondered how I could reach the bushels of pears growing at the top. There aren't enough solid horizontal laterals to climb the thing safely. A few times we set up a tarp to catch falling pears.

These are great pears. I think end of July and early august they should be able to pick. They are sweet, juicy and yet crunchy. Love them.

thanks everyone!

I'd suggest thinning now- just go in and remove everything that points downward or upward from the laterals (scaffold branches that are attached to the trunk). That will help limit regrowth in the spring. You'll be amazed at how much green you'll have lying on the ground when you're done!

If the scaffolds have developed branches that are growing into competition for the branch from which they are growing -that's more than about 1/3 the diameter of the scaffold- cut those competitive branches off where they attach. Leave the pencil-sized branches that grow horizontally off of your main scaffolds- those should become fruiting wood.

Expect to continue thinning for the next few weeks as new growth tries to replace what you removed. It takes a while to develop a clear picture of how it all works (I'm certainly still figuring it out) but the tree will forgive a good number of mistakes.

I tried picking these pears at different times towards the end of summer, and letting them ripen inside.....each time the pear was still pretty crunchy, kind of sour, and just didn't taste like a pear to me. I ended up letting most of them just fall on the groudn and rot.....which they then fermented and attracted bees and wasps......it was just too much in my busy schedule to deal with. I may just end up cutting it down sometime.

Is it possible you picked them all too early? My very rookie understanding is that you can know you definitely waited too long to pick if the inside (by the core) is starting to get soft/mushy already. Did you keep picking some up until that point?

Even if you don't like your pears for fresh eating (no matter when they're picked), they may be great for canning or pear sauce -- some pears make horrible sauce (like gritty soup), but others make sauce I prefer to applesauce -- or other cooked/processed uses. You might want to consider those options before you cut it down, especially if it seems to be producing with zero care.

I hope you let them fruit next year and try refrigerating them for about two weeks before allowing them, a few at a time, to ripen on the counter top. Many pears benefit from this approach.

Pick them when the neck gives a little to a firm squeeze.

You've got a lot of tree there, and I can appreciate the problem in dealing with fallen fruit. I think you could benefit by thinning out quite a bit of the tree- at least one third of it. Take branches off where they attach to the trunk, leaving the ones that are spaced well and attached at good, not too-steep angles. You could start any time now and expect to continue into the summer.

That is a nice looking tree. That's something I really like about pears...they grow to such perfect trees...naturally.

It is pretty thick (as many have said) and would benefit from some pruning work. Personally I'd do a little pruning to thin and allow some light in, but I'd mainly leave it alone. It's producing and looks as healthy as can be.
Being a street tree like that, it's aesthetic value to me would be worth a lot. It will produce more pears than you'll probably want anyway.
Looks like there is some suckering at the base...get rid of those first, then the vertical water sprouts and crossing or damaged limbs, clean up the low growth for neatness and to make mowing underneath easy.
For me, that would be all I would do. That would increase the fruiting potential slightly while retaining the beautiful natural shape.

That is a pretty tree.
How tall is it?

Looks like a Kiefer pear to me. They definitely mature later than most pears. My neighbors doesnt pick his until early November, and then lets them set at room temp for up to 2 weeks before he eats them. They arent the best tasting pear IMO either, my description of taste would match yours as you descibed it. They are a very hardy pear, nice looking tree.

They are best for canning where they can be used while hard but after they turn yellow on the tree. Only decent as an eating pear and most people won't bother although some are fond of them. They never get the full sweetness of a quality pear.

This is based on my experience with them in SE NY. Here they don't ripen until almost Nov.