I started May 19 last year and had a great time. I ran into snow on one occasion. There weren’t very many people on the trail except in popular areas like Mansfield and Camel’s Hump. The Inn at the Long Trail was closed. I did share shelters with one other person two or three times, so I wasn’t totally alone.
The spring wildflowers were all out, and in places the trees were still bare, adding to the views.
On the whole, I’d say it depends on how you feel about lots of solitude. I tolerate it pretty well so I enjoyed myself. You might feel differently.
The GMC says not to do the trail in May, as you probably know. There are parts that are closed – although it’s probably not enforced.
I went anyway, because it had been a dry year up to the point when I started, and I thought I could use common sense not to wreck the trail. The trail was mostly in good shape, except for a couple of days after heavy rains. It was pretty squishy on Killington, and I avoided the top of Stratton on a rainy day partly to avoid damage. But I could see how damage could be a real problem on a bad year. So I guess, use your judgment on that issue.
Bob McCaw