Bear Mountain is the highest peak located entirely within the State of Connecticut. For a long time, it was thought to be the highest point, period. There is a massive stone cairn marking the summit, six feet high on its western side but cascading forward to the east, and a marble plaque erected in the 1880s to memorialize the mountain as the high point of the Nutmeg State.
Much to everyone's surprise, advanced surveying techniques later revealed that Bear Mountain had been mismeasured and that nearby Mt. Frissell, with its southern slope in Connecticut but its summit in Massachusetts, actually contained the highest point in the state. This was a significant blow to state pride, but the redirection of those high peakers now making the trek to Frissell has not diminished the popularity of Bear Mountain, which affords glorious eastern views to those that make the steep climb to the summit.
Nature abhors a static boundary. The forest of the Taconic Plateau encompasses more than 36,000 acres in three states, but laws and regulations that pertain to it and the land that sustains it differ in each jurisdiction. There are three, separate Federal Forest Legacy designations covering the Plateau, but they are evaluated on a state-wide basis and do not consider the context of the full forest. Each state has its own policies for how it manages its protected lands within the Plateau, and each has its own laws concerning working forests, conservation easements, rare species, and watershed protection.
Meanwhile, the rattlesnakes wander across state lines, often ranging over 4 miles from their winter dens. Not long ago, Connecticut's DEP estimated that there were perhaps 75 "Massachusetts" bears in the northwest corner of the State. Now these and many more are understood to be residents rather than part-time visitors.
The rivers flow off the Plateau to the Housatonic or the Hudson as they please without regard to any geo-political limitation. About a 1/4 of the Plateau drains from Massachusetts and the northwestern slopes of the Taconics into Roellif Jansen Kill and from there to the Hudson River. The rest forms part of the Housatonic drainage, like Webatuck Creek below Boston Corners in New York that runs into Connecticut and out again before joining the Ten Mile River and returning to the Housatonic below Bull's Bridge in Connecticut. The girdling belt of seepage wetlands that surrounds the Plateau in all three states depends of the same, shared forest to provide nutrient poor, calcium rich groundwater to its springs and fens.
There is a whole series of heavy granite monuments demarcating the state lines running up impossibly steep slopes and deep into the forest. They were installed in the early 1900s and replaced even older markers, but it took more than two centuries of European settlement before the boundaries became fixed in their current position. Boston Corners, a triangle excised from Massachusetts along its hypotenuse but even more effectively by the eastern barrier of the Taconic Plateau, was once a lawless outpost of the Bay State and site of an illegal, bare knuckle prize fight in the 19th century before it was ceded to New York State. The "Oblong" of Dutchess County that today forms a 3/4 mile wide panhandle at its northeast corner was part of a larger dispute of longstanding concerning New York's eastern boundary with Connecticut. There was ultimately an exchange with New York that gained Connecticut its own panhandle, the 8 mile wide "gold coast" region in the southwest corner of the State that today is the wealthiest county of the country.
The Taconics form a natural barrier and the boundary disputes were, in part, a question of who controlled the few passes that allowed passage from the Hudson River Valley to the Berkshires and the Housatonic. But it was also about iron ore and the colonial iron industry that evolved in this region. Rival claimants to Indian patents and mining interests from CT, MA and especially the Livingstons of New York, vied for control of the area's bog iron, the charcoal provided by its virgin forests and the marble valleys that provided lime for the region's smelters. It was a war of tenant verses landlord, of shots in the dark and lonely cabins flaring up in the night. The Race family, which gave its name to one of the most beautiful mountains of the Plateau, also gave their lifes to the firebrands of Livingston's overseers. Jan Hollenbeck was a partisan in this low intensity border war who fought the Livingstons but ultimately retired to Connecticut, where a tributary of the Housatonic now carries his name.
All that is in the past, but there are families on Mt. Washington, in Salisbury and Ancram, who descend from those early settlers. The Spurrs, Whitbecks and Van Deusens were here at the end of the 17th century. My paternal grandmother, Clara Livingston, came from an impoverished branch of that manorial tree and the old Patroon, Robert Livingston, who once dominated eastern New York from the Catskills to the borderlands with Connecticut and Massachusetts.
These mountains are higher than they appear. Someone in Millerton, New York, feels little natural connection to someone in Egremont, Massachusetts, even though their lands are within the same, shared forest. From any vantage point in the valleys, the Taconics appear as long ridgelines rather than an elevated plateau. In Massachusetts, they are indiscriminately thought of as "the Berkshires" even though they have a completely different geologic heritage than the adjacent Berkshire Hills. The name "Taconic Plateau" is a recent invention of The Nature Conservancy's awkwardly named Berkshire Taconic Landscape Program and has not yet entered common usage. The ecological boundaries are trumped by definitions of town, county and state, but function according to other, older processes than these administrative distinctions.