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While Bear Mountain (elevation 2,316 feet) is the highest summit in Connecticut, the highest point in that state (elevation 2,380 feet) is on the south slope of Mount Frissell, along the Mount Frissell trail, a little to the west of the summit (elevation 2,653 feet). Most highpointers reach it by a rather short route starting high up in the col between Mt. Frissell and Bear Mountain, at an elevation of around 1,800 feet. While planning a trip to the CT highpoint I decided to look for more interesting ways of reaching that point. This trip eventually became a four day highpointing expedition in the Berkshires.

County highpointers may want to attempt to reach the two nearby New York county highpoints: Dutchess County (the summit of Brace Mountain) and Columbia County (on Massachusetts state line 0.3 mile west of Alander Mountain). The Resources section has information on maps of the region; for those who do not have a paper map I am including a Topozone map of the area.

Routes to Mount Frissell

I have not attempted to list all possible routes to Mount Frissell, just those that I think a highpointer is most likely to use. Many other routes can be put together using any of the maps in the resources section. Since most highpointers do not hike as part of a large group I have not described any routes which require a car spot.

From the East

A high valley separates the South Taconic Range from the Bear Mountain-Mount Everett Range to its east. Three trailheads, all at elevations of over 1,600 feet, lie on a road in that valley. More ambitious hikers can start east of the Bear Mountain, climbing over it, descending to the valley, and then ascending Mt. Frissell.

The Standard Route

I am including this for completeness, it is well described in all highpointing books. The trail starts on the Massachusetts side of the border with Connecticut, on a road called East Street in MA and Mount Washington Road in CT. It first goes over Round Mountain (open summit, good views), climbing very steeply. After Round Mountain the trail descends to a col then climbs, very steeply again, to the summit of Mount Frissell. The summit itself is wooded, but there are good views on the eastern ledges.

From the summit it is a short distance to the highpoint on the boundary, passing the south ledges with good views. The tri-state point (MA, CT and NY) is a bit further along the same trail. The round trip distance to the highpoint is 2.6 miles, with roughly 1,000 feet of total elevation gain. This gives a book time of 1:50.

Note that there are two sections on this short trail that the Massachusetts and Rhode Island Trail Guide (see Books below) describes as "very steep". A friend has used the word "climbing" to describe those two sections.

Jeep Road from Mount Washington Road

This easier approach uses an old jeep road (called the Brace Mountain Trail in the Massachusetts and Rhode Island Trail Guide) that starts from the Mount Washington Road about 1.2 miles south of the state border. It climbs part way up Brace Mountain and meets first the southern end of the Ashley Hill Trail and shortly after the South Taconic Trail. Turn right (north) on either of these to reach the Mt. Frissell Trail west of the tri-state point. Follow that trail eastward, passing the tri-state point and the Connecticut highpoint before ascending to the summit of Mt. Frissell. Round trip distance is 3.4 miles with an elevation gain of about 600 feet, for a book time of 2:00.

County highpointers will want to go south for a short distance on the South Taconic Trail to get to the summit of Brace Mountain, the highpoint of Dutchess County. Others may want to reach it for the excellent views.

These two routes can be combined to make a loop, which will include a road walk of 1.2 miles.

Over Bear Mountain

This route takes you over the highest summit in Connecticut on the way to the state's highpoint. Take the Undermountain Trail, off CT 41 north of Salisbury, to its junction with the AT. Go north (right) on the AT over Bear Mt. and down the steep North side. From the top you go about ¾ mile down very steeply and as soon as the trail flattens out there is an unmarked trail to the left (if you get to the junction with Paradise Lane and signs to Sages Ravine you've gone too far). Follow this trail for about 0.8 miles to the Mt. Washington Road, almost across the road from the start of the Mt. Frissell Trail. Follow that trail over Round Mountain and the summit of Mount Frissell to the Connecticut highpoint. Round trip distance is 9.6 miles with an elevation gain of 3,000 feet, book time is 6:15.

This may be turned into a loop by using the Paradise Lane Trail to bypass the summit of Bear Mountain in one direction, the distance is unchanged but there are 500 fewer feet of elevation gain for a book time of 6:00.

Loop over Alander Mountain

A scenic loop over Alander Mountain starts at the Mt. Washington State Forest Headquarters on East Street in the town of Mt. Washington, Massachusetts. Take the Mount Alander Trail to the summit of Mount Alander. There are two choices from the summit. You may go down by the South Taconic Trail, going over the highpoint of Columbia County, NY, or you may take the Alander Loop Trail which joins the South Taconic Trail. In either case, follow the South Taconic Trail to its junction with the Mt. Frissell Trail, and take that trail eastwards passing the tri-state marker and Connecticut highpoint on the way to the summit of Mount Frissell.

Return by following the Mt. Frissell Trail back west slightly beyond the tri-state marker, then take the Ashley Hill Trail north to join the Alander Mountain Trail a short distance from the trailhead. Round trip distance is 11.2 miles, with 1,600 feet of elevation gain, book time is 6:25.

It is obviously possible to add Brace Mountain to this loop. Before heading east on the Mount Frissell Trail follow the Taconic Crest Trail south for 0.5 mile to the summit of Brace Mountain, then return to the Mount Frissell Trail. There is minimal elevation gain, so add 0:30 to book time.

From the West

South Taconic Trail from the South

This starts at the Rudd Pond Farms residential development in New York State. The South Taconic Trail starts gently going eastwards along the side of a field. It soon starts to climb steeply, over very rough terrain, and there are some scrambles up ledges that I found unpleasantly exposed (your tolerance for exposure may well be greater than mine!). Reaching the ridge it goes north over Brace Mountain (highpoint of Dutchess County, NY), to its junction with the Mt. Frissell Trail. That trail passes by the tri-state point, then the highpoint of CT, and then climbs to the summit on an open slope with great views. The round trip distance to the summit of Mount Frissell is 6.6 miles with about 1,500 feet of elevation gain, book time is 4:00. This is the route that I used to do Mount Frissell and Brace Mountain in the spring of 2003.

Summary of Distances and Elevation Gains

To summarize, here are the distances, elevation gains and book times of the various possible routes to Mount Frissell:

Routes to Mount Frissell
Route Distance Elevation Gain Book Time
Mt. Frissell Trail from east 2.6 1,000 1:50
Jeep Road 3.4 600 2:00
Over Bear Mountain both ways 9.6 3,000 6:15
Over Bear Mountain one way 9.6 2,500 6:00
Alander Mountain Loop 11.2 1,600 6:25
South Taconic Trail 6.6 1,500 4:00

Mount Frissell in Winter

Many highpointers think of Mount Frissell as an easy highpoint, largely because of the short (but steep!) standard route. Many are unpleasantly surprised when they attempt it in winter. The Connecticut access to the standard route is closed in winter, and the route itself can be tricky, with the steep rocky climbs covered with snow. Before attempting the trip, read the trip reports by DickMc and markv.

Directions to Trailheads

The Undermountain Trail starts on a state road well shown on all maps, all the others start on more obscure roads.

Trailheads on Mt. Washington Road

The Alander Mountain Trail, the Mount Frissell Trail and the Jeep Road all start on the Mt. Washington Road, a portion of which is called the East Street.

From Massachusetts

Follow Rt 23/41 through South Egremont, where Rt 41 branches off to the right (south). Almost immediate the Mount Washington Road (clearly signed) branches off to the right. After 8 miles a road branches off to the right going to Bish Bash Falls and Copake Falls (again, clearly signed). Continue straight ahead past it. After about a mile the Mt. Washington State Forest Headquarters is reached, it has a large parking lot and is the trailhead for the Alander Mountain Trail.

The Mount Frissell trailhead is further south (my guess from the map is about 2½ miles) just beyond the state line. The Jeep Road starts about 1.2 miles south of the state border.

From Connecticut

NOTE: This road is unplowed and closed in winter.

Take Factory Street (also known as Washinee Street) about 0.1 miles south of the junction of Rts 41 and 44 in Salisbury. After about half a mile bear left on the Mount Riga Road, following it for about three miles. Then turn right onto the Mount Washington Road. Follow that road for 3.3 miles to the state line for the Mount Frissell Trail, or 2.1 miles to the jeep road.

Undermountain Trail

The trailhead is on the west side of CT 41, about 3.5 miles north of Salisbury.

South Taconic Trail

Drive on NY 22 either 5.5 miles north of the traffic light in Millerton, or 7.5 miles south from the intersection with Rt 344 to Copake Falls. Then go east on White House Crossing Street and drive to its end. Here take a left on Rudd Pond Road, and after 0.3 miles take a right onto Deer Run Road into a residential development (Rudd Farms). Take a left on to Quarry Hill Road and follow it to a small parking area at the edge of the woods.


I have made no effort to produce a comprehensive list of resources, and have just listed books, maps and web sites that I have actually used myself.



Online Resources

There are many highpointer trip reports on the America's Roof website.