Killington, Vermont

The scale of Killington's terrain is the primary reason guests come and the primary driver of vacation rental demand in the area. Six interconnected mountain peaks — Killington, Skye, Bear, Ramshead, Snowdon, and Sunrise — offer everything from wide beginner cruisers to sustained expert steeps like Outer Limits, one of the most sustained mogul fields in the East. The K-1 Express Gondola, which accesses the main Killington Peak summit, is the fastest way to the top-to-bottom terrain that represents the best of what the mountain offers. The mountain receives both natural snowfall (typically over 250 inches per season) and extensive snowmaking coverage that allows it to open earlier and close later than any other Vermont resort. The season typically runs from mid-October through late April, with some years seeing skiing into Memorial Day weekend. The vertical drop of 3,050 feet is the second-greatest in New England, behind only Sugarloaf in Maine. Weekend and holiday lines at popular lifts can be long; mid-week skiing is dramatically less crowded and often offers the same conditions for a fraction of the hassle.

Killington's bike park is among the best-developed downhill mountain biking operations in the eastern United States. With more than 40 miles of purpose-built trails across multiple difficulty levels and gondola-accessed descents from the 4,000-foot summit, it draws serious riders from Boston, New York, and Montreal who come specifically for terrain that does not exist in the flatlands they call home. The trail network includes dedicated beginner and intermediate flow trails with smooth berms and tabletops alongside gnarly expert lines with technical rock features and significant drops. The K-1 Express Gondola carries bikes to the summit, and the Killington Summer Pass provides gondola access throughout the operating season. The Spartan Race — a major obstacle course racing event held at the resort — brings an additional wave of fitness-focused visitors in summer.

The Long Trail — Vermont's historic footpath running 272 miles from the Massachusetts border to the Canadian line — crosses the Killington summit and traverses some of its most spectacular terrain in this section. The climb from Route 4 at the Sherburne Pass trailhead to Killington Peak is approximately 3.5 miles with 2,200 feet of elevation gain; the summit views on a clear day take in Mount Washington, the Adirondacks, and a sweep of Vermont's Green Mountains in both directions. The Appalachian Trail shares the Long Trail in Vermont and diverges east at Sherburne Pass, making this one of the more heavily trafficked sections of both trails. The Inn at Long Trail at Sherburne Pass has operated as a hiker's hostel and pub since 1938 and is worth a visit for both the hiking culture and a post-hike Guinness in the stone-floored tap room.

Killington's après-ski culture is the liveliest in Vermont and among the most active in the eastern United States. The cluster of bars along Killington Road — including the Wobbly Barn, which has operated as a ski town institution since the 1960s, and the Lookout Tavern with its outdoor deck — fill quickly after the lifts close and maintain energy into the evening. The atmosphere is genuinely festive on peak weekends, with live music, competitive pricing on drinks, and the particular social energy that comes from a couple hundred people who just spent eight hours doing something physically demanding in the cold. Killington's nightlife is one of the draws for younger vacation rental guests who want the full ski vacation experience rather than just the skiing.

Pico Mountain, connected to Killington by a shuttle bus and included on the Killington lift pass, offers a quieter alternative to the main resort with 48 trails on a 1,967-foot vertical drop. The mountain has maintained its independent character — smaller lift lines, a more intimate base lodge, a loyal local following — even within the Killington Pass system. Families with young children and skiers who prefer to avoid the crowds and energy of the main resort often prefer to spend their days at Pico. The terrain is weighted toward intermediate and beginner runs, making it a logical choice for groups with mixed skiing ability.

The land surrounding Killington includes a network of state forests and reservoirs that provide four-season outdoor recreation beyond the resort's managed terrain. Calvin Coolidge State Forest encompasses over 26,000 acres of managed woodland with hiking trails, camping, and hunting access. The small lakes and ponds — including Kent Pond at the base of the mountain and Colby Pond in Plymouth — offer swimming, fishing, and kayaking in summer, and ice fishing and snowshoeing in winter. Plymouth Notch Historic District, the birthplace and summer home of President Calvin Coolidge, is twelve miles south of Killington village and provides a striking contrast: a perfectly preserved Vermont village that looks as it did in 1923, surrounded by mountain terrain.