Ah Connecticut. A common route to the CT high point, at 2,454ft, involves starting near they base of Round Mountain and hiking to the summit. Then, you hike down Round Mountain and to the base of Mt. Frissell and to the summit. Then, you hike partially down Mt. Frissell, cross the state line into CT, and achieve the highest ground in the State of CT. The trail is about 1mi from the trailhead to the top of Mt. Frissell, but don't let that fool you. In between the trailhead and the summit lies the steep Round Mountain where you might find yourself scrambling occasionally. In the winter, when we chose to visit, snowshoes are a must and poles helped get up (and down!) both Round Mountain and Mt. Frissell.

The drive to the trailhead is paved (until the last bit) and can wind through Great Barrington, MA (if coming from the north), or Salisbury, CT (if from the south) all while taking in views of the Berkshires (a continuation of the Green Mountains in Vermont and part of the Appalachians). Even during the winter, we found the entire route to be plowed and easily accessible in an all-wheel drive mid-sized SUV.

The trailhead itself is well-marked and red-blazes will take you straight up the side of Round Mountain. At the summit, you'll find scrub brush and the obligatory cairn visitors have constructed. Don't be fooled, though, you're only halfway there!

From the top of Round Mountain, the red blazes continue to the right (north) and down the far side. The views from Round Mountain are great and you can see several surrounding lakes.

As you follow the red blazes down Round Mtn., you'll wind around a bit, then head up Mt. Frissell. Near the summit, the trail will split and the right-hand trail leads to the summit. The summit of Mount Frissell is in a wooded area with no views and marked with a yellow sign posted about 5ft off the ground (about 10 yards on the right). After returning from the summit to the red blazed trail, continue on along the shoulder of Mt. Frissell until you find another cairn on your right (upslope). When there's no snow, you'll find the high point benchmark with a green pole sticking up (4-6in). When we visited, snow covered everything.

Gear Recommendations:
We highly recommend snowshoes if visiting when there is snow on the ground. We rented some MSR Evos from REI on the way and they helped us move quickly and reach the summit and back in less than 3 hours (with several stops to enjoy the views, have lunch, etc.).

We also recommend trekking poles as they will help ascending and descending the, at times, steep routes up Round and Frissell.

Along with the snowshoes and poles, leg gaiters (see our gear review for more info) will help when you inevitably step down into 2ft of snow (as we did on several occasions). Our gaiters kept our feet and legs dry and cozy during the hike. We purchased ours from Amazon for about $14.

Here are the ones we used:

While the CT high point may not have the best views, several spots along the shoulder of Mt. Frissell offer great photography opportunities, as does the summit of Round Mountain. Enjoy the hike and bag another Appalachian high point!