Having lived in SF for many years, I was lucky with endless road trip options leading to outdoorsy destinations. In NYC, it can seem the opposite, trapped! I stumbled upon a great list of pit stops in the Hudson Valley and Berkshires. Starting in Tarrytown and winding through Dover Plains, New Marlborough and ending in North Adams, this 4 day guide is a perfect rustic retreat with art, waterfalls, hikes, riding vintage plains, culinary treats and bed and breakfasts.