Early October in Borderland State Park means Halictidae all over the place! Not sure which species or genus these are (Auguchlora, Agapostemon, Auguchlorella?).
In this first photo, the protruding part is the bee’s glossa, similar to the tongue.
This utterly fascinating caterpillar seems to be an ant or beetle mimic on its front end! The Caterpillar identification group suggested something like Dichomeris (e.g. https://bugguide.net/node/view/26909) as a good place to start. And here is a Dichomeris caterpillar with a similar webbed leaf: https://bugguide.net/node/view/668363/bgimage.
When dragonflies mate, the male tries to hold onto the female as long as possible, in order to reduce the chances another male will mate with her.
Tetragnathid spiders, Tetragnatha sp. perhaps.
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