Killington: 12 miles E of Rutland; 160 miles NW of Boston; 93 miles SE of Burlington
In 1937, a travel writer described the village near Killington Peak as "a church and a few undistinguished houses." The rugged, remote area was isolated from Rutland to the west by imposing mountains and accessible only through the daunting Sherburne Pass.
That was before Vermont's second-highest mountain was developed as the Northeast's largest ski area; before a wide, 5-mile-long access road was slashed through the forest right to the mountain's base. And it was before Route 4 was widened and upgraded, improving access to Rutland considerably. Today this is one of the most heavily traveled routes through the Green Mountains, and that early travel writer would be hard-pressed to recognize the region today.
Killington is plainly not the Vermont pictured on calendars and postcards. The region around the mountain boasts Vermont's most active winter scene, with loads of distractions both on and off the mountain. The area has a frenetic, where-it's-happening feel in winter. (That's not the case in summer, when the vast, empty parking lots trigger either a mild, where's-everybody-gone panic or relief at the sinking prices of lodging.) Those most content here are skiers who like their skiing BIG, singles in search of aggressive mingling, and travelers who want a wide selection of amenities and are willing to sacrifice some of that quintessential New England charm for a broader range of diversions.
About a dozen miles to the west, the rougher-edged city of Rutland lacks the immediate charm of other Vermont towns, but has a rich history and an array of convenient services for travelers. (It's also home to a huge annual state fair each fall.) If you like the action of Killington but want a lower-budget alternative, bivouacking down in the valley in Rutland and traveling by day to the ski area is a popular option, since there's a ski bus that whisks you from Rutland up to the slopes.
Looking for Classic New England? -- If you're in search of classic New England, consider staying in quaint Woodstock (see earlier in this chapter) and commuting the 20 miles to the slopes. It's not a quick ride, but it's scenic. Or stay at one of the resorts tucked into the folds of other nearby mountains, such as the Mountain Top Inn in Mendon.