KENT, Conn.—Sal Lilienthal, owner of the Bicycle Tour Company in Kent and author of two books about the American Revolution, will lead a free Revolutionary Spies Bike and Kayak Tour on two weekends, Aug. 16, 17, and 23 and 24, visiting Revolutionary War-era sites between lower Manhattan and West Point.

While the guided ride and kayaking is free, participants will provide their own equipment and transportation to and from the destination points. “I haven’t really envisioned that people will do all four stages,” said Lilienthal. “For instance, if someone from New York City wants to ride the first stage with us, they could take the train back from Setauket. Or if a group is riding, they might arrange for a support vehicle to pick them up at the end of the day.”

It might seem strange that a man who conducts bike tours for a living would provide a four-day adventure for free, but Lilienthal says the donation of his time is rooted in his family’s immigrant experience. 

“First, all of my grandparents were immigrants,” he said, “and they had such a deep appreciation for our country. My grandfather alluded to the cultures in Europe and America, back and forth almost every day. He would talk about the assassination of Duke Franz Ferdinand as if it were yesterday. Secondly, the American Revolution is a hobby of mine and I’m in the right business. This is just a fun ride.”

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Indeed, Lilienthal has promoted visitation to Revolutionary sites for years. He wrote “Revolutionary Battles” in 2014. “The original concept was to bike 25 Revolutionary battlefields from Quebec to Savannah, Georgia,” he said. “The other one was ‘Revolutionary Connecticut,’ an online Revolutionary-themed tour book I wrote with Central Connecticut State University history professor Mary Collins. We created nine routes in Connecticut around people like Ethan Allen and Nathan Hale. People can download that at ctamericanrevolution.com.”

The tour will begin at 8 a.m. on Saturday, Aug. 16, at the Washington statue on Wall Street and will continue 71.1 miles that day to Setauket/Port Jefferson, ending for the day at the Jeanne Garant Harborfront Park just east of the Port Jefferson ferry.

The following day, Aug. 17, the tour resumes at 8 a.m., at the park with an 18-mile kayak crossing of Long Island Sound to Bridgeport.

The following weekend, Saturday, Aug. 23, the journey picks up at the Caleb Brewster homesite at Ellsworth Park in Black Rock (Bridgeport) and continues 65.2 miles to Tarrytown, NY, ending at Patriots Park, the site commemorating the capture of British spy John Andre.

The tour ends Aug. 24, with a kayak launch from Losee Park in Tarrytown, goes 14 miles up the Hudson River to Verplank’s Point at Cortlandt Waterfront Park, and thence 15.7 miles by bike to West Point, finishing at the Washington statue at Trophy Point.

Along the way, the Revolutionary Spies trip will features stories about Thomas Knowlton, commander of Washington’s first intelligence unit, classmates Nathan Hale and future spymaster Benjamin Tallmadge (later a Litchfield resident), friends and acquaintances Austin Roe, Anna Strong, Caleb Brewster, Abraham Woodhull, field operative Robert Townsend, as well as Benedict Arnold and his Loyalist second wife, Peggy Shippen, who conspired with Major John Andre, head of the British Secret Service. 

Even those who do not recognize all the names, many of whom were featured in AMC’s historical drama “TURN: Washington’s Spies,” can connect to their stories. The tour starts by Washington’s statue on Wall Street. George Washington was first inaugurated as President at Federal Hall and Trinity Church in the background served as a center for colonial life. Many revolutionaries are buried in the church’s cemetery, including Alexander Hamilton and Horatio Gates. While occupied by the British, American field operatives gathered information in lower Manhattan. 

The tour then crosses the East River over the Brooklyn Bridge following one of Culper’s routes through Brooklyn, Queens and along the once-British controlled north shore of Long Island. In-the-field operatives traveled undetected along this route, gathering information from Loyalists and British soldiers. Abraham Woodhull coordinated the operation from Setauket. 

1773 Yale classmates Nathan Hale and Benjamin Tallmadge were teachers after graduating and exchanged letters about freedom, liberty, and drinking too much Madeira. Due to the failure of Hale’s spy mission, Tallmadge designed an intelligence system with operatives already in place from his childhood hometown, Setauket, NY. A stone and bronze marker at the Stamford Yacht Club commemorates Tallmadge’s 1779, 130-person raid on Long Island, sailing out of Stamford Harbor.

The next day’s kayaking trip across Long Island Sound could be disrupted if the water is too choppy—“We will adjust according to weather and attendance,” Lilienthal said—but is slated to leave from the Jeanne Garant Harborfront Park just east of the Port Jefferson Ferry. Stratford Shoal Lighthouse marks the halfway point and is the site of many “Devil’s Belt” shipwrecks. Sailing and rowing a whaleboat, Caleb Brewster, Abraham Woodhull’s childhood friend, transported coded messages from Setauket to his home at the Black Rock section of Bridgeport, then considered to be part of Fairfield.

From Caleb Brewster’s homesite on a hidden cove in Bridgeport, the Second Connecticut Light Dragoons often galloped through Yorktown Heights carrying the spy ring’s intelligence dispatches to Washington’s Hudson Valley headquarters. The relatively safe direct route to Verplanck’s Point provided the Dragoons a way to cross the Hudson River at Kings Ferry. 

While American and British spy networks developed, the Redcoats raided Connecticut from Long Island Sound, landing at Compo Beach (Cedar Point) Westport, then headed to their main target, Danbury’s supply depot in 1777. Ironically, Benedict Arnold, later a traitor and Redcoat spy, rushed to defend his home state as a Continental Army General. The British shot his horse out from under him at the Battle of Ridgefield.

When Washington first met with French General Rochambeau at Hartford in September 1780 to plan a joint offense against the British, Benedict Arnold plotted with British Major John Andre to attack West Point, the Patriots’ most strategic location. Peggy Shippen, Arnold’s Loyalist second wife, also conspired with the British Major. 

On Andre’s return trip from his rendezvous with Arnold, en route to New York City, American militia men John Paulding, David Williams and Issac Van Wart captured him at Tarrytown. The bicycle tour on stage 3 finishes at Patriots Park, where a monument commemorates the event. 

The Spy Tour continues on Stage 4, kayaking up the Hudson River, following Arnold and Andre’s treasonous sail on the 16-gun British sloop HMS Vulture. After paddling up the Hudson River to Verplanck’s Point from Tarrytown, the tour continues north cycling to West Point. 

Washington was constantly on the move, rarely staying in one place very long. He often travelled around West Point and the Hudson Highlands reviewing the Americans’ strategic positions, where intelligence dispatches were delivered to him directly.

Navigating the section of river between West Point and Constitution Island was particularly challenging due to unpredictable tides, a double bend in the river and strong winds funneling through a narrow opening between the hills. 

For the American Colonists, failure to defend West Point meant New England could be divided from the rest of the colonies, ending the possibility of enduring freedom and liberty outlined in the Declaration of Independence. Blacksmiths even forged an enormous chain, anchored on both sides of the river and held afloat by rafts as an obstacle for British ships. Some links are said to have been forged in Salisbury.

Benedict Arnold’s family was stationed at the Robinson House on the east side of the river, near West Point. When Paulding, Williams and Van Wart captured Andre, exposing the treasonous plot, Arnold fled down river to the Vulture moored near Tarrytown, missing Washington’s return from Hartford by hours.

The spies uncovered a British plot to attack the French Army when it first arrived at Newport, possibly their most significant accomplishment. As a response, Washington leaked a counterattack plan to invade New York City if the Redcoats left for Rhode Island. The British cancelled their initiative, which potentially saved the French Army and the entire Revolution.

The tour finishes at the Washington Equestrian statue on West Point’s campus.

Those interested in exploring this portion of Revolutionary history should contact Sal Lilienthal at 860-309-1449 or Explore@RevolutionaryBattles.com.

Kathryn Boughton has been editor of the Kent Dispatch since its digital reincarnation in October 2023 as a nonprofit online publication. A native of Canaan, Conn., Kathryn has been a regional journalist...

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