DRive in approach
The Mount Washington Road on the CT side is closed until May. This is clearly posted on the Massachussetts side. THe last 10 miles of road are muddy but maintained with gravel in the mushy spots. When the road into CT is closed, the trailhead at the border is obvious because you cannot go any further.
The Hike
My wife, two sons and I decided to head in the direct way, primarily following the CT-MA border. It is a beautiful path through mountain laurel and abundant phyllite exposures. It is steep on a few short (100 feet) pitches but just Adirondack style trail steepness, definitely doable for any able bodied person. My three-year old loved it!
The summit of Frissel has no views but the views from Round and the south side of Frissell are worth the hike.
There is an abundance of blow down between Frissell and Round. It causes some very short detours (20 feet) and step overs. It added significently to our hike time because the three-year old wanted to inspect each one.
We decided to descend to the tri state marker and then loop back on the alternate approach out to the closed Mount Washington Road and then back north on the road to the car. It made for a great 4 mile loop.
It looks like the path along the CT-NY border between the tri-state marker and the jeep road is no longer maintained. It was obvious that from the tri state marker the defined trail continued west. Presumably it intersects with the jeep road further west. The CT_NY border trail was overgrown and had noticeable erosion.
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