During the War of Independence, both sides recognized the critical
importance of the Hudson River. The river was a critical transport
route from the interior to the coast in an age when good roads were virtually
non-existent. In British hands,, however, the Hudson would
present a formidable barrier cutting New England off from the other colonies
to the south. It would also facilitate free movement of British forces
between Canada and New York City--large naval vessels could navigate the
Hudson all the way up to Albany, and smaller craft could move quickly by
water to and from Canada via Lake Champlain. British control of the
river would hinder intercolonial trade, facilitate British troop movements
both within the region and to and from Canada, and would effectively prevent
the Continental Army from operating in the Hudson Valley and north, regions
that typically provided substantial amounts of manpower to the Patriot
cause.
While the Hudson Valley is generally rolling terrain for most of its
length, the 15 mile wide belt of the Hudson Highlands in the vicinity of
West Point constitutes a crucial choke point on the river.

The Hudson in the Highlands region was at the same time an invaluable
transportation route and a daunting obstacle if controlled by an enemy.
The river is 40 to 200 feet deep and quite wide, ranging from 1/4 mile
before West Point to over a mile near Cornwall (its widest point in the
region). The river is actually an estuary, with significant tidal
action all the way to Albany--a factor which further complicated navigation
by sailing vessels.
Recognizing the importance of the Highlands in controlling the Hudson,
the Continental Congress began investigating the possibility of fortifying
the region as early as 1775. The first fortifications were
planned in August of 1775 by Bernard Romans, a relative novice in the field
of military engineering. Romans identified the "S" bend in the river
before West Point as an ideal location for fortifications--sailing
ships travelling upriver from New York at this point would have to negotiate
the tight curves with multiple tacks, and would also have to contend with
current, tidal flow, and shifting winds channelled by the high hills lining
the valley--conditions that would make them easy targets for cannon on
the banks. Romans chose to build his initial
fortifications on the east side of the river along low-laying Martalaer's
Rock, soon renamed Constitution Island,
a decision soon decried by more experienced military men.
After the Constitution Island fortifications were captured and destroyed
by the British in 1777, the rebels chose to focus their efforts on fortifying
the commanding heights across the river at West Point. Throughout
the war, George Washington kept substantial forces, often the main body
of the Continental Army itself, in the Hudson Highlands to preserve the
rebel hold on the river.
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