Check out Nordic napping. I used to clean out a spot large enough for the stroller, bundle kid up and strap in. Seriously best nap for kiddo and super productive for me!

Second Lake St. Catherine! We've been bringing my now 5 year old since he was about 9 months old.

Castleton might be a good fit. It's a college town and has more diversity than some of the other areas. It's right off of 4, a pretty direct route to Killington and about 15 minutes from Rutland so you still get that small VT village feel but you're still close to a "bigger" city

I'm in NY, literally 1 mile from the VT border. I think we spend more time in VT than NY for both recreation and shopping

There's also the unofficial non-compete clause they have with Price Chopper. You'll never see a PC near Wegs locations and vice versa.