Flirtation Walk at West Point is arguably the most beautiful trail in all of the Hudson River Valley due to its historical significance and extraordinary location. It sits at a most spectacular point along the river although significant erosion and massive overgrowth of trees and shrubs hide much of its spectacular beauty and views. Portions of what we know today as Flirtation Walk made up the Revolutionary Supply Road. The cannons and gunpowder, food, and other supplies that were needed to fortify the Highlands Fortress were brought to the garrison in the 1700’s by Captain Cornelius Gee on board the sloop Federal. What remains a mystery is where exactly on the point did Captain Gee’s ship land and what trail did they utilize to get the heavy weaponry and other supplies up to the Plain?

In the photo to the right you see a small valley that exists from Gee’s Landing area to the left of the Flirtation Walk path as represented by the yellow line. Was this more protected and flatter gully the actual road that they used? Archaeological investigations can tell us more in the future.

Flirtation Walk, originally named Chain Battery Walk in the mid – nineteenth century, sits on a fairly narrow high ridge line close to the river and would have been in full view of the enemy troops should they have ever threatened the Great Chain and river batteries. This is represented in the map to the right by the orange line. There were almost no trees anywhere on Fortress West Point during the Revolutionary period as they had been cut down for miles to expose sight lines, and to provide timber for the fortification construction and  heat and cooking fires for the soldiers.

There is a firsthand documented description of Captain Gee’s House located on the Revolutionary Supply Road by his granddaughter who visited there. In his expansive drawing of Fortress West Point, L’enfant shows a house in that vicinity in his illustration from 1780. There are also remnants of a house foundation still in existence today. A thorough archaeological investigation of that house foundation and of the valley path itself might provide clues to how artillery and supplies were brought into West Point.

FLIRTATION WALK

What we now know as “Flirtation Walk” at West Point was established by Superintendent Richard Delafield during his tenure as superintendent from 1838-1845 and named “Chain Battery Walk.” He purposively extended privileges of cadets to access the trail as he saw it as a means of bringing attention to what had been the Revolutionary Supply Road and the fortifications that remained there. He proceeded to have Yorktown carved high on a ridge on the walk in large letters and enhanced the trail with massive plantings of lilacs. The much faded carving of Yorktown still exists. Unfortunately, cadet orienteering classes crawl down it every year further damaging this historic element. Remnants also still exist of the large lilac stand beneath the Yorktown carving, but they struggle to survive because extreme overgrowth of trees blocks the sun. Remnants of another mass of lilacs at the “west point” and Lanthorn Battery are also barely surviving for the same reason. The beauty of the walk is often referred to in cadet letters and yearbooks and cadets can be seen in the photos below.

Today, Flirtation Walk is used by cadets as primarily a running trail and the American Revolutionary fortifications and carvings are mostly forgotten. Also on Flirtation Walk are the carvings initiated by Superintendent Henry Bremerton memorializing the Mexican American War but they are overgrown by trees and bushes. President / General Grant and  Robert E. Lee and many other West Pointers fought together in these Mexican battles and would eventually go on to fight each other in the Civil War.

“I give it as my fixed opinion, but that for our graduated cadets, the war between the United States and Mexico might, and probably would have lasted some four or five years, with in its first half, more defeats and victories falling to our share; whereas, in less than two campaigns, we conquered a great country and a peace, without the loss of a single battle or skirmish.” – General Winfield Scott

For many years, Flirtation Walk served as the only venue on post for privacy from officers (as many graduates can attest ) from the inception of the Military Academy to about 1975. It was a favorite place for marriage proposals.

There are both lower and upper trails of Flirtation Walk, however, access to the upper trail is compromised at Chain Battery because of serious erosion caused by damaged irrigation pipes. An addition cadet memorial exists at the upper entrance.

The Olmsted Brothers Plan

In the very early twentieth century, West Point hired Richard Law Olmsted’s firm, the Olmsted Brothers, to create a landscape plan for West Point. Olmsted was the preeminent landscape architect in America responsible for the preservation and development of Central Park in New York City. He designed many major city parks throughout the United States including landscape and roadway designs for the following:  Acadia National Park, the Great Smoky Mountains Park,Yosemite Valley, Atlanta’s Piedmont Park, entire park systems in the cities of Portland and Seattle, and many more. His firm completed a comprehensive design to preserve Flirtation Walk with particular attention paid to the still existing American Revolutionary fortifications elements of the trail.

In 2002, the West Point Garrison contracted with the U.S. Army Engineer Research and Development Center Construction Engineering Research Laboratory to complete a comprehensive 120-page document that lays out a Historic Landscape Management Plan for the U.S. Military Academy. This includes recommendations for what is needed along the trail to enhance the natural landscape, expose the views and restore the former beauty of the trail, as well as preserve the American Revolutionary history. Little has been done over the past 100 years to implement any of those plans. It includes the Olmsted Firm’s recommendations for specific plantings of natural elements along the trail and where viewsheds should be opened. Although the recommendations were never implemented, they remain viable for today and could bring back this beautiful element at West Point.

CADET MEMORIALS:

Several cadet memorials exist on Flirtation Walk erected by cadets in honor of classmates who died during their time at West Point. For example, the bench pictured below was erected in honor of a cadet Richard B. Sheridan, Jr., who died while playing during a football game at the Yale Bowl in 1931. Another bench has been installed on the path honoring cadets lost from the Class of 1986. There are approximately eight cadet memorials along the walk thus far.

Kissing Rock

Located on Flirtation Walk, the path beneath “Kissing Rock” is highly eroded as well as many other areas of the upper and lower trails. Tradition says if a cadet does not kiss his or her sweetheart under the rock then West Point will crumble. Flirtation Walk was memorialized in a Hollywood movie of the same name in 1934, and featured mega stars Dick Powell as a West Point cadet and Ruby Keeler as his hard-to-get love interest, as well as Pat O’Brien, future governor of California.