Whether or not someone has any out of state skiing this season really depends upon the answers to the questions.....do you intend to comply with stated travel restrictions and do you intend to answer honestly if you are involved in any contact tracing?
Realistically there’s no way for VT to know if you quarantined for 14 days before going to VT or not, or for NY to know you travelled to VT.....unless you get sick and contact tracing happens, and you answer related questions honestly. How willing are people to take on the remote financial risk of penalties if not honest? Not something I really want to risk. Flying into NY airports for western travel could get dicey, if there’s enforcement at the airports. Maybe the EWR loophole stays open for a NY traveller to slip in under any enforcement, but who knows? So many variables right now.
For me, sad as it is, as things stand I’m not sure I see myself skiing out of state this season. Too many hoops to jump thru to stay on the up and up. While I may be working from home (easier to quarantine), even if I were inclined to bend the “rules” (which I’m not saying I am), my wife isn’t, and she works in a public school. She can’t afford quarantine. She’s also concerned (as she should be) that if the kids or I don’t all comply, and one of us gets sick, and she spreads COVID to her school and causes any kind of shut down....it will reflect badly on her. I have to respect that.
I don’t foresee a great season, unless we get lots of snow and ADK backcountry is in play. Still waiting for Whiteface to start selling tickets for MLK weekend but nothing yet. Midweek powder chasing day trips in NY could be easier this season (since I haven’t used much PTO since March)...if online tickets are available.