Vermont county highpoints are a hiker's dream come true. All the highpoints are true "summits"; there are no liners. Of the 14 counties that make up the state, all but one have highpoints that are over 3,000 feet, and all of these can be reached by good hikes. The exception is Grand Isle County, an island in Lake Champlain which has two points that poke their heads a full 200 feet above the level of the lake (and only 270 feet above sea level).
All of the Vermont county highpoints are within a fairly short distance of a road. Indeed, peakbaggers from Massachusetts and New Hampshire often complain that on trips to Vermont the driving time is longer than the hiking time! Many of these mountains have ski areas on them, and I suppose that in some cases the lifts operate in summer; being a hiker I have made no inquiries.
These notes are meant to give you the flavor of these trips, for directions check the Vermont County Trip Reports on the County Highpointers web site.
Grand Isle County is in the northwestern corner of the state, a group of islands in Lake Chaplain. The two highest points (of equal elevation on maps) are two tiny hills just off roads. One is on publicly accessible ground, the other requires parking at the Snowfarm Vineyard, whose owners are most welcoming to highpointers. We were caught in a thunderstorm while there, and left soaking wet, so we did not return to the store to buy any merchandise. It is a long drive from most places, and as noted above is the only county highpoint in this state that does not offer a worthwhile hike.
Franklin and Orleans Counties are normally hiked together. The main summit, Jay Peak, is in Orleans County and is reached by a short but steep climb up the Long Trail (about 1.7 miles each way, with 1,700 feet of elevation gain). The slightly lower Big Jay is reached by an old herd path which, in 1999, was illegally cleared and made into a trail. While it is not being maintained it is quite easy to follow. It is about a mile (each way) from Jay Peak to Big Jay, with roughly 400 feet of elevation gain each way.
The highpoint of Essex County is East Mountain, the site of an old radar station. There is a road to the summit, but it is gated (many locals seem to have keys, a family drove up to fish at a beaver pond while we were there) and is an easy four mile walk each way, with about 1,600 feet of elevation gain. The summit buildings have suffered severely, both from the weather and from vandals. The views are excellent, and I found the view of the familiar New Hampshire summits, viewed from an unfamiliar angle, rather unusual.
Caledonia and Orange Counties again have highpoints (Signal and Butterfield Mountains) that are usually done together. These two mountains are the only ones in Vermont that require a bushwhack, through largely open woods with lots of blackberries. I hiked them in shorts, a painful mistake!
Chittenden and Lamoille Counties (the Chin and Adam's Apple of Mount Mansfield) are done together by those who set out to do county highpoints, though peakbaggers rarely climb Adam's Apple until they become interested in county highpoints. It is possible to gain a lot of elevation by car (toll road) or gondola, but there are a large number of excellent hiking trails; many are described on the Mount Mansfield page on my peakbagging site. In good weather there are excellent views from both summits, as well as from the ridge that goes from the Nose to the Chin. The ridges on Mount Mansfield have the largest area of alpine vegetation in Vermont. One of the best routes is to go up to the summit station (near the Nose) by the Haselton Trail, go along the ridge over the Chin and up Adam's Apple, then descend by the Long Trail. This is about seven miles (total) with under 3,000 feet of elevation gain. Another excellent approach is from the west, taking the Sunset Ridge Trail to the Chin, then descending to Taft Lodge by the Profanity Trail (steep, but still easier than the Long Trail) and going up to Adam's Apple. Return by the Long Trail, the scramble going up is easier than going down. Roughly the same length as the Haselton-Long Trail loop.
Washington County has two mountains of equal hight (Camel's Hump and Mount Ellen).
Camel's Hump is a beautiful mountain: beautiful to look at and beautiful to look from. It is the only 4,000 footer in Vermont without a ski area on it. It has the second largest area of alpine zone vegetation in Vermont. It also has a large number of trails, most are described on the Camel's Hump page on my peakbagging site. The commonest routes are between five and eight miles with around 2,500 feet of elevation gain.
Mount Ellen, Washington County's other highpoint, is a much less interesting mountain. It is often done, both by peakbaggers and by county highpointers, together with Mount Abraham. When done alone it is best approached from the west, by the Jerusalem Trail and the Long Trail (about six miles and 2,600 feet). Details of the other approaches are found on my peakbagging web site.
The highpoint of Addison County is Mount Abraham, which rises above treeline and has excellent views in all directions. It is the home of Vermont's smallest area of alpine vegetation. As noted above, it is often combined with Mount Ellen. The shortest approach to it alone is from Lincoln Gap, along the Long Trail (about five miles and 1,600 feet). For other routes see my peakbagging web site.
The highpoint of Rutland County is Killington Peak, the last of Vermont's five 4,000 footers. The usual route is from the west by the Bucklin Trail, which joins the Long Trail slightly below the summit of Killington Peak, at the Cooper Lodge. From there a short but very steep spur trail goes to the summit (about seven miles and 2,500 feet). Peakbaggers may want to bag Pico Peak on the same trip, check my peakbagging web site.
The highpoint of Windsor County is Gillespie Peak, one of many bumps on a section of the Long Trail that rises from Brandon Gap. About 6½ miles with 1,700 feet of elevation gain. You may want to read a report of my trip to it.
Bennington County is the one mountainous county with a drive-up highpoint, Mount Equinox, which can be reached by a toll road. It can also be reached by a most enjoyable hike, about six miles and 2,900 feet of elevation gain. It has excellent views.
The highpoint of Bennington County is Stratton Mountain, an almost 4,000 footer (elevation 3,936 feet) with a fire tower that gives 360° views. The easiest way is an in and out trip along the Long Trail from the Arlington-West Wardsboro Road (about 7½ miles and 1,700 feet). A more interesting trip is to do a loop, continuing north on the Long Trail to Stratton Pond, then returning by the Stratton Pond Trail (11 miles and 1,900 feet).