Hi Michael, 

Sorry about your pear tree! It appears to be a fungal leaf spot. This can happen in wet weather. From the photo I can't tell for sure which one, but the procedure is the same. Take and destroy the affected leaves this fall and prune to open up some room for air to circulate among the branches. More airflow and room for light to penetrate will help during overwintering. Also, I would recommend removing any fallen leaves from the soil underneath the tree and keep on that to make sure the fungus isn't allowed to overwinter in the soil.

In a slightly unrelated note, A helpful step to monitoring the health of trees such as yours is getting a soil test. UVM has resources for you if you decide to do so (https://www.uvm.edu/extension/agricultural-and-environmental-testing-lab). If you have tested recently, ignore this advice - but doing so could give you a good picture of the health of your soil, and will cue you as to whether or not fertilizer is needed (and what kind). Below are some resources that may help - hopefully this all helps! 

Resources: 

https://extension.umn.edu/fruit/growing-pears

https://extension.psu.edu/pear-disease-leaf-blight-and-fruit-spot

https://newswire.caes.uga.edu/story/4768/leaf-spot-disease.html

https://netreefruit.org/pears/diseases/fabraea-leaf-spot

https://www.uky.edu/Ag/kpn/kpn_05/pn050718.htm

https://extension.umaine.edu/fruit/growing-fruit-trees-in-maine/diseases/