What you should be tracking is Watt hours per mile. (At the bottom of the driving display if you swipe right you will see your watt hours per mile for the current trip, since last charge, as well as Trip A and Trip B).
I've had my Model Y LR for two months (and 5,600 miles - I love driving that car). Most of my highway driving (in MI, OH, PA, MD, VA) had been at around 270 Wh/mi. That's averaging 75 mph with cruise/Autopilot.
If I have a bicycle on the bike rack, that jumps to 350 Wh/mi (still at 75 mph). When I hauled a 6x12 solid UHaul trailer it jumps to around 450 Wh/mi. And when hauling the trailer I kept the speed at 55 mph. Wind resistance is a powerful force, even with just a single bike in the rack.
Assuming there is 72.5kWh usable in the battery, that works out to about 270 miles of range clean, 200 miles with a bike, and 160 miles driving at 55 mph with a trailer.
In practice on the road I tend to top off at 80% and stop for recharge around 25%, which works out to about every 2 1/2 hours (my bladder has limits). So far range has not been a problem. East of the Mississippi there are plenty of Superchargers.
As for NH, I can't wait to get up there sometime and trek up Mt Washington. I can't even begin to imagine what regenerative braking would be like on the way down.