The Two-spotted Tree Cricket is a large arboreal species found in woodlands, edges, and thick stands of young trees. They can be hard to spot, as they are generally high on tall plants or in trees.
An interesting feature of this cricket: Males chew holes into leaves which they then place their wings up against while singing. The leaf becomes an extension of their wings and amplifies the sound. See pictures of this behavior at the BugGuide Species Account.
iNaturalist shows most observations recorded May through November, with large spike in numbers in July, August, and September.