The Legend of Lover’s Leap

By Amy Leiser, Executive Director
Monroe County Historical Association

An old tale from Monroe County’s history recounts the legend of a love between and Indian princess and an early Dutch settler. The story, which may or may not be true, was first recorded in Luke W. Brodhead’s 1870 book,
The Delaware Water Gap, Its Legends and Early History.

As the story goes, Princess Winona was the beloved and only daughter of Chief Wissinoming, the noble leader of the Minisink. While the chief ruled all of the land along the Delaware and Susquehanna rivers to the Atlantic Ocean, the headquarters of the tribe was located near Shawnee Island and present-day Smithfield Township, Monroe County.

Winona grew up in the 17th century, during a time of relative comfort and peace. She was a great beauty, but also possessed great character, strength, and kindness. When European settlers began to arrive in the area, they were welcomed by the native peoples, including Winona. These new inhabitants were Dutch settlers who traveled south from the Hudson River in search of new areas in which to reside. The lush and beautiful lands surrounding the Delaware River were already appealing to the settlers from Holland, and, when a scouting party discovered a rich deposit of copper, the land became even more desirable. A Dutch settlement filled with families was quickly established across the Delaware River from Shawnee in modern-day New Jersey.

(There are varying historical reports, records, and research debating the infrastructure surrounding the copper mines; many believe that the 104-mile Old Mine Road in New Jersey was built by the Dutch to transport the copper to ships on the Hudson River near Kingston, N.Y., to carry the ore back to the Netherlands.)

In Brodhead’s account, a young man named Hendrick Van Allen was sent to the new settlement to oversee the mines that were of considerable financial interest to the mother county in Europe. Hendrick was described as fair, well-mannered, accomplished, and well-suited for a life of adventure. While visiting with one of the families in the Dutch settlement, Hendrick overheard the lady of the home speaking highly about the Indian princess. Princess Winona was well-liked by the Dutch women who lived in the new settlement, and the new settlers quickly befriended the native princess.

Because of Winona’s kind demeanor, the Dutch women enjoyed when she would visit the settlement. Princess Winona, in turn, took pleasure in the women’s company and was curious to learn their customs, manners, and styles. After learning of Winona, Hendrick was determined to meet the princess, and a close friendship developed. They shared many interests, including hunting the abundant game along the Delaware River – Hendrick with his rifle and Winona with bow and arrow.

During this time, when Winona was enjoying life with her new neighbors and Hendrick was traveling between Kingston and the settlement, tragedy struck the Indian village – Chief Wissinoming died. Not only was this the saddest time in Winona’s life, but the chief’s death caused a power struggle among local Indian tribes. While several neighboring tribes tried to invade Wissinoming’s fertile land, each was defeated. According to custom, Manatamany, Winona’s younger brother, naturally became successor to his father’s chiefdom.

In the meantime, relations between the European settlers and the native people became strained when a young and well-liked colonist was killed. The basis of the conflict centered around who was allowed to occupy and cultivate the Great Shawano Island, a fertile swath of land in the middle of the river that was revered by both peoples.

To resolve the conflict, and return friendship and peace to the two cultures, Winona proposed a two-part solution. First, her people would retain the Great Shawano Island and give the settlers the Island Manwallamink. Second, in return for the terrible loss of the young settler, Winona would sacrifice her own life. The settlers, who adored Winona, vehemently refused the offer of her life. When Hendrick returned from his business affairs in the Hudson Valley, the residents relayed the offering Winona had made, including her proposal and the devotion she showed for a continuing peace between the native people and the settlers. The settlers continued to speak highly of Winona, and her loyalty made her even more intriguing to Hendrick.

After hearing their account, Hendrick spent less time in New York and more time among the Dutch settlers. Indeed, when his immediate responsibilities at the mines were satisfied, Hendrick sought out Winona, and their friendship blossomed. According to Brodhead, Hendrick “should have discovered the spark he was kindling, and the danger of fanning to a flame that which, in a breast like Winona’s, would continue to burn forever.” Hendrick spent endless hours talking with Winona about all of his worldly experiences and travels.

Winona was enthralled with his stories, but was saddened that she could not return (in her mind) conversation as exciting as his. She focused on sharing tales of the natural beauty of the land she inhabited, her people, the forests, the river, and her noble heritage.

Wanting to share her world with Hendrick, Winona offered to show him the beautiful view of the Pohoqualin (Delaware Water Gap). While Hendrick had urgent business to attend to in Kingston, the two agreed that on his next visit to the settlement, they would travel in her little red canoe to the foot of the cliff, where they would hike up an Indian path and climb to the summit.

While seeing to his duties of oversight of the mines, Hendrick was ordered to stop all mining operations – the English government had acquired ownership of New York. Hendrick was emotionally devastated – not only did he have to abandon the copper mines, but he had to tell Winona the sad news that he would be returning to Europe, leaving her forever. Hendrick realized he had fallen in love with Winona, and he also knew that he could never marry her or take her with him to Holland.

As agreed, when Hendrick returned to the settlement, he and Winona met so she could show him the beautiful view of the gap. Winona paddled Hendrick down the Delaware River in her red canoe until they reached the trail. On the trail, Winona described every rock, brook, tree and view. Hendrick was noticeably quiet, and Winona questioned his unusual behavior. Hendrick had not yet decided how to tell Winona the sad news that he would be leaving the settlement forever. As they walked to the summit, Winona could sense something was wrong with her dear friend; he was very quiet and unlike himself. Winona begged him to tell her his thoughts.

With that, Hendrick regretfully revealed his orders to Winona, in the form of a sealed letter from his employers. He read it to Princess Winona. After hearing the news, Winona stood and calmly delivered a lengthy speech, ending with, “Farewell, brother! Tutor, lover! Winona’s sun has set forever.”

Princess Winona walked to the edge of the cliff. Hendrick ran to her side, catching her in his arms in an attempt to save his love from falling over the edge. The two reeled on the precipice, and, stumbling, they fell to their deaths, embraced in one another’s arms.