The Connecticut River and the American Revolution

To mark the 250th anniversary of the Declaration of Independence, Estuary presents the first of two stories about the Connecticut River’s maritime contributions to the Revolutionary War.

When a break with England looked like it was inevitable and coming quickly, the 13 very separate American colonies had to figure out how to work together. The British army and navy were bigger, better organized, and better financed.

The only fighting forces in the colonies were separate state militias. All men between 16 and 50 were required to serve in their colony’s defense. Militia companies were made up of local townsmen—farmers, merchants, shoemakers, and the like—and few had military experience beyond periodic training days. As important, there was no command structure that crossed state lines. We needed an army and a navy—and quickly. But there was resistance. A standing army was too much of a reminder of what the colonists were trying to get away from.

While the Continental Congress debated establishing an army (which it did in June 1775) and navy (October 1775), the states bolstered their militias, and all but two (Delaware and New Jersey) established state navies. In addition, both Congress and the states authorized privateering. Civilian owners of ships and boats were licensed to arm their vessels and go after British ships to disrupt British trade and to capture British navy ships. In Connecticut, for any British ship taken, the state received half the value of the ship and cargo; the other half was split between the privateer owners, officers, and crew.

Connecticut’s towns on the Connecticut River played a significant role in both privateering and the Connecticut State Navy. Shipbuilding and maritime trade were major industries there, and colonists had the know-how and the patriotic fervor to go up against the mighty British navy.

Connecticut provided about 200 privateers of the approximately 1,800 authorized by the states and Congress. Towns like Hartford, Wethersfield, Middletown, East Haddam, and Saybrook (which later split into the towns of Old Saybrook, Westbrook, Essex, Deep River, and Chester) sent privateers down the river and out into Long Island Sound and beyond.

The Privateering Hart Brothers
One Sunday morning, two months after news of Lexington and Concord reached Saybrook at the mouth of the Connecticut River, Rev. William Hart was preaching to his congregation. Suddenly, the sound of cannon disrupted the service. As Samuel Tully recorded in his diary July 9, 1775, the British navy had seized and then released several vessels off Saybrook. Three days later he reported, “Harts Vessel Arrived, having escap’d.” The Hart in question was likely Rev. Hart’s oldest son, 29-year-old William Hart, Jr. Beginning in 1776 he commanded the First Regiment of Connecticut militia light horse cavalry. But this did not prevent him from investing heavily in the highly risky business of privateering.

Eleven privateers operated out of Saybrook, of which the five Hart brothers owned at least four. William Hart, Jr., got involved perhaps as early as 1775; in December 1776 he was part of a group of investors in the privateer Fanny.

Fanny was described as “an exceeding[ly] fast Sailing Bermudian Briggantine.” Fellow Saybrook-ite Captain Azariah Whittlesey was at the helm. In February 1777, on his first voyage to Martinique and back, Whittlesey captured the British Apollo off Barbados with 297 enslaved Africans on board. Whittlesey also captured a brig “laden with Fish,” and a sloop carrying barrel staves. The three prizes were taken into Martinique and the cargo sold. This is possibly the only tie between William Hart (who, later, was an enslaver) and Whittlesey and the slave trade.

In April, Whittlesey captured the 180-ton British ship Cesear off Barbados bound from London to Jamaica carrying a large quantity of dry goods and other cargo. The investors were so pleased with themselves, they presented Gen. George Washington with a token of their regard: “two pieces of fine Irish linen—which we beg you would do us the honor to accept as a small memorial of the very great respect & regard we bear to your excellency.” With this record of success, a short time later Fanny was purchased by the Massachusetts State Navy.

Whittlesey next sailed at the helm of the brig Neptune, commissioned December 31, 1778, with William Hart’s 23-year-old younger brother Joseph Hart as the investor. But Whittlesey’s luck had turned. On its way back from Guadeloupe in April 1779 with a cargo of rum, sugar, and coffee valued at £6,000, Neptune was driven ashore on Martha’s Vineyard by the British privateer Tryon and captured. Whittlesey was freed in a prisoner exchange soon after.

Whittlesey continued to sail privateers for the Harts and others, but by 1780 the Harts were investing in privateers captained by their youngest brother, Elisha Hart, then 22. Elisha’s start in privateering is shrouded in mystery. The first record is his appeal in September 1779 to Benjamin Franklin, then the Continental Congress’s envoy in France, for money to return home. Franklin had secured the release of Captain Hart from England in a prisoner exchange.

In June 1780 Capt. Hart took over the helm of the Hart-owned Retaliation from Whittlesey. He recaptured two American vessels from the British and captured four British sloops including one carrying British troops.

As Hart recounted in a letter to Connecticut’s Governor Jonathan Trumbull, while flying a decoy British flag he sighted the British sloops south of Long Island coming from New York and took chase.

I discovered she had no guns, but appeared full of Men Elligantly Dressed. I then Supposed her to be a Pleasure Boat from the Fleet, which I then saw Lying In the Narrows and was within One League of them and in full View of the City and More than a League within the Guard Ships.

Hart hailed her but her commander refused to come on board. “I then ordered Down my English Colours, Ran out my Bow Guns and Told him if He did not Come on Board I would Sink Him Immediately. He then Hove out his Boat and Come on Board. I Immediately Man’d the Prize and Took out the Prisoners.”

Capt. Hart’s next cruise, towards the end of 1780, was for trade. But it did not go well. On the way to the West Indies with a cargo of horses, Retaliation sprang a leak and had to put in to Bermuda, a hotbed of British privateering. The ship, captain, crew, and cargo were taken to South Carolina as a British prize. Capt. Hart was imprisoned there, but was released to continue privateering aboard another Hart-financed privateer Restoration, commissioned in May 1781.

In September 1781 (the same month the British, under turncoat Benedict Arnold, burned New London) the Connecticut Courant reported that a British frigate had driven Restoration onto a sandbar off Long Island. Capt. Hart and his crew managed to repel the attack and capture a British captain and eight soldiers. British reinforcements soon arrived and demanded they surrender. Hart refused and negotiated an even exchange for his prisoners and the rest of his men to return home on parole. Having been captured a third time by the British, the Courant simply reported, “Capt. Hart accordingly returned home with his people the Wednesday after.”

This may have been the last of the Hart brothers’ involvement in privateering. They had won and lost in the art of privateering, though every British ship taken was a feather in Saybrook’s cap. The experience was the brothers’ entrée after the war into the West Indies trade—a very active and lucrative, though still risky, business conducted from many of the lower Connecticut River towns.

The Connecticut River and the Connecticut State Navy
Meanwhile the State of Connecticut, recognizing the vulnerability of both its citizens and its maritime economy along 600 miles of coastline (100 miles as the crow flies), established a navy a few months before Congress acted.

Connecticut’s navy only ever amounted to 13 vessels. In an effort to get up and running quickly, in August 1775 the brig Minerva (a two-masted, square-sailed ship) belonging to Capt. William Griswold of the Connecticut River town of Wethersfield was selected as one of the state navy’s first two ships. Minerva was retrofitted for a crew of 40 seamen and 40 marines. While being outfitted in Middletown, supplies of cannon, powder, and cannonballs were collected in Saybrook at the mouth of the river.

Minerva was ready for service by early October 1775 and was ordered to capture British troop and supply transports heading to Quebec. But for reasons unrecorded, Minerva’s crew refused the orders, returned to port, and the crew dismissed. The ship was returned to Capt. Griswold.

Minerva later sailed as a privateer and proved her mettle—but perhaps too well. On July 31, 1781, she captured the British Hannah, bound from London to New York with a cargo valued at £80,000 sterling. This was said to be the largest prize taken by a Connecticut privateer and may have been the impetus for the British attack on New London—the state’s largest port and center for privateering—a little over a month later.

After the state navy’s misstep with Minerva, in 1776 Connecticut took a different tack. It commissioned the construction of its first purpose-built warship, the Oliver Cromwell, from Uriah Hayden’s shipyard in Essex (then part of Saybrook). The 300-ton, three-masted brig—three times the size of Minerva—was launched in June 1776.

The Oliver Cromwell, however, was not used in defense of Connecticut’s shoreline nor local shipping, but to harass and capture British ships (like privateers) as far away as the West Indies. In three years of service, captain and crew took nine British ships, primarily in the Caribbean, before being captured in June 1779. She was rechristened the HMS Loyalist under the Royal Navy. Two years later, the French recaptured her, rechristened the ship for a third time as the Loyaliste, and returned her to the US a few months later. But her days in the state navy were over.

One of the most colorful vessels of the Connecticut State Navy was the invention of the nation’s first submarine—the Turtle—by David Bushnell of Saybrook. Read more about the Turtle in the Fall 2026 issue.

Elizabeth Normen is managing editor of Estuary magazine and a historian. This story is drawn from her new book, Awakenings and Revolutions: The Harts, Saybrook, and the New Nation (2026) published by the Old Saybrook Historical Society. Visit saybrookhistory.org for more information.