Born and bred in southern New England, moved from the Worcester area in 2010, now a Coloradan x 7 years. Who knows if and when we'll move back but I do miss it some! Have to say that my biggest adjustment was coping with the traffic when we arrived. Unless you have chronic lung disease, hiking < 8000 feet elevation should be a non-factor after the first few weeks. The sun is nice; seasonal affective disorder is nonexistent. They don't plow the roads here much when it snows, banking on the sun melting it. This works mostly, except when it doesn't....
My $.02: Three critical factors. Tolerance for lots of people; cultural things; and job availability/diversity. The Front Range has many people, many cultural opportunities, and many job possibilities, including one of the lowest unemployment rates in the country and a high minimum wage. Cost of living is high- not as high as Boston or NYC but comparable to the nicer parts of Central MA and CT.
Co Springs is up and coming, and the cost of living is going up too. Politics are pretty conservative, so infrastructure isn't the greatest, but it is close to lots of hiking.
Telecommuter? Don't care much about opera and national-class theater? Can't stand traffic? Then avoid the Fort Collins to Colorado Springs corridor. Bozeman might be the better choice, or SLC, or Salida CO, or Durango, or Glenwood Springs, or even Grand Junction. We have neighbors who moved to Bend, OR a few years ago to escape the busy-ness here, but they just moved back here because it was TOO quiet for them there.
Like a wide variety of great restaurants? Have a flexible work schedule, so you can commute and hike/camp off-hours? Don't mind traffic jams? Like to see Broadway-bound shows before they get there? Denver might be a good choice, just know that you and many thousands of others will be driving west to compete for camping spots every weekend of the summer. I-70 is not unlike I-93.