PFSense on Hyper-V - Can't Access VMs from hypervisor
I ended up figuring out my problem. I had a vpn client (Forcepoint to be exact) I noticed every time I'd try to ping that IP, the forcepoint client would prompt me to login. I suspect it's looking for traffic outside my network, and if it think's i need to VPN in, it's prompting me to login..
Anyways, I had already created and deleted my static route a million times, but I also noticed I had a loop when running traceroute. It just kept hopping to my router (192.168.1.1) endlessly. I uninstalled forcepoint client and everything is working now.