CT State Highpoint/Tri-point Out and Back

This trail begins at the Mount Frissell Trailhead just over the Massachusetts border in Connecticut. Immediately the trail is narrow but well-trod as it is for the route's entirety. Soon it begins to climb up the slope of Round Mountain. This climb is steep, rocky, and at times requires scrambling. However not long after, the trail levels off as it reaches the summit of this mountain. Here, there are wonderful unobstructed views of the surrounding area and of Mount Frissell. The trail then begins to head north as it dips slightly before climbing once again up Mount Frissell. While this climb is also steep, there is much less need for scrambling. The trail then levels off briefly and a spur trail leads to the summit of Mount Frissell. There is a sign at this point, but any views are obstructed by trees. The trail then heads southward and approaches the state line once again. Here lies the CT highpoint (2454 feet - only a little over a hundred feet taller than Bear Mountain) which is marked by a USGS pin and a small, improvised cairn. The trail then continues to descend toward the tri-point. Here again, some of the rocks are difficult and require some scrambling on the way back. After a little while, the trail comes to an opening that is home to the tri-point border marker. From here the route turns back and leads all the way back to the parking lot at the trailhead.

For a very long time, the summit of Bear Mountain was thought to be the highest point in Connecticut. While it is true that the summit of that mountain is the highest peak in the state, the highest point is actually on the south slope of Mount Frissel whose summit is just over the border in Massachusetts. This trail leads to that point.