Vanished Port: Middletown and the Great Era of West Indies Trade

By Erik Hesselberg

A Vanished Port Middletown lies at a great bend in the Connecticut River, 26 miles up from where it flows into Long Island Sound. A four-lane highway by the river at Middletown separates the city from the waterfront. Between the highway and Main Street are acres and acres of asphalt—more surface parking than this city of 48,000 could hope to fill on its busiest days. Standing on the upper deck of a two-story parking garage, you see the wide gray river sweeping eastward toward a narrowing between low green hills in the distance. From the parking garage, a walkway takes you up to Main Street and the Romanesque-style brick police station. On a sidewalk nearby is a granite pillar with a bronze plate and cryptic message: “This plaque marks the graphic location of Center Street; a place that will always live in our memories.” Once, on this expanse of asphalt where cars are now parked, were living neighborhoods to which the bronze plaque refers. Center Street was the hub of the Sicilian community.

The Italian district was the last vestige of something quite different, an earlier civilization in a manner of speaking. To find out what that was, you have to cross Main Street and walk south a block to a handsome brick edifice with a wrought-iron gate and lilacs in the front yard. This is the old General Mansfield House, seat of the Middlesex County Historical Society. Here are found documents and memorabilia on the vanished port of Middletown.

The shades are always drawn in the Society’s upstairs rooms, but there are glimmers in the darkness. Fine antique furniture, some of it shrouded in white sheets, fills the ghostly space. There are Chippendale highboys, elegant mahogany tables, graceful carved chairs, curving empire sofas, and bow-front bureaus—relics of a lost era. In the shadows, you sense the stern gaze of a distinguished gentleman in a powdered wig, a painting of a person who lived long ago. He is wearing a buttoned topcoat over a ruffled shirt and billowing cravat. A spyglass is in this mariner’s left hand. This is Capt. William H. Van Deursen.

Mattabesset was the name given to the bend in the river by Native Americans, meaning “the end of the carrying place.” The rich alluvial soil enabled the local tribes to grow a surplus of maize, beans and squash. Wesleyan University Geology Professor Emeritus Jelle Zeilinga de Boer describes the Connecticut River Valley as American’s first grain belt.

The river colony was called Middletown three years after its settlement in 1650. From the first, colonists were shipping lumber, cattle and fish, and later grain to the West Indies, where slave plantations, which now fully occupied the islands, offered a ready market for river valley agricultural products. Yankee traders brought back sugar, salt, coffee, fruits, and spices, especially molasses and rum. Shipbuilding began in Middletown in 1669, and soon three shipyards were busy outfitting vessels for trade with the Caribbean.

Enterprising merchants from all over were drawn to the river port. By 1750, Middletown was the largest and richest colony in Connecticut. This shipping wealth is reflected in the many elegant furnishings now stored at the Historical Society. The Barnum map of 1824 shows the port of Middletown at its zenith, when the maritime district comprised much of the downtown—a 47-acre area extending from Ferry Street, six blocks south to Union Street and east of Main Street down to the river. In this seafaring community stood 200 houses, including elegant mansions of merchants and sea captains. A score of warehouses lined the waterfront, and pushing out into the wide river, a dozen wharves from which sailed full-rigged ships and schooners, West Indies-bound.

William Southmayd was an early West Indies trader, arriving in Middletown in 1667. Beginning with farming and later shipbuilding, the Southmayds were soon among the largest property owners in the maritime district. In 1737, Joseph Southmayd, William’s eldest son, was granted exclusive rights to operate the ferry across the river to what was then called Chatham.

Captain Van Deursen was a seafaring man from a Dutch New York family who came to the busy port of Middletown during the American Revolution. He was 26 when he was offered the command of the privateer Middletown, a 200-ton, 14-gun brig with a crew of 30. The year was 1781. Middletown was owned by Chauncey Whittlesey, a Yale-trained minister now a provisioner to the Continental Army. Whittlesey is remembered gratefully for procuring for the troops 4,500 gallons of “good merchantable West India rum.”

The merchants that put Middletown on the map were mostly outsiders, many arriving in the decades before the Revolution with ready capital. These men were a clan, gathering to discuss business over glasses of Madeira at Bigelow’s Tavern on Main Street, or at the Gaylord Tavern nearby. They were nearly all Episcopalians, attending their new church on South Green, established in 1750. Matthew Talcott and Samuel Bull came down from Hartford, Lemuel Storrs from Colchester, the Alsops, John and Richard, from New York. The Henshaws arrived from Boston, while Philip Mortimer and Arthur Magill were of Scottish ancestry. Benjamin Williams came to Middletown from Bermuda.

The elegant brick Georgian house of Capt. Benjamin Williams, the present deKoven House, is still there near the water, but the big, square homes of Matthew Talcott and Samuel Bull on Main Street are long gone, along with the beautiful riverfront mansion of Philip Mortimer, with its avenue of buttonwood trees leading down to the water. A handsome, gambrel-roofed Colonial home at the foot of Ferry Street, where the merchant Arthur Magill lived for a time, appears in a collection of 200 or so Historical Society photographs of buildings in the maritime district that were demolished during the redevelopment years. These photographs were taken for real estate purposes, but even this undistinguished record shows that our waterfront neighborhoods compared favorably with streets in Salem and Newburyport.

The Alsop House on the Wesleyan Campus (now Davison Art Center), a pink stucco Tuscan villa, was built between 1838 and 1840 for Richard Alsop IV, grandson of the celebrated merchant Richard Alsop II. The elder Alsop’s original dwelling stood at the corner of Main and Court streets, but all records of it are gone. However, the Federalist mansion of Richard’s son, shipmaster Joseph Wright Alsop, was a landmark on lower Washington Street. Westward about a mile on the crest of Indian Hill Cemetery stands the Alsop family mausoleum, a huge carved brownstone Romanesque monument. Out in front, a weathered slab of sandstone bears the name of the merchant Richard Alsop.

When Richard Alsop died in 1776, his will was 50 pages long. The estate was valued at more than 35,000 pounds, including a “large sum of money in Jamaica”—this at a time when 50 pounds bought you a house. Alsop & Co. was an East India trading house that shifted to the profitable Caribbean trade in the mid-18th century. The new focus came under Richard Alsop, who moved the operation to Middletown, as the largest port in Connecticut, on the way to becoming the largest seaport between New York and Boston.

Alsop’s death, on the eve of the Revolutionary War, brought some difficult years. Complicating matters was Richard Alsop III’s decision to become a poet (he was one of the celebrated Hartford Wits). The family appears to have accepted young Richard’s flight into poesie, even though bred to commerce. Joseph Wright Alsop, Richard’s younger brother and a seafaring man, continued the business, but only after their mother, the resolute Mary Wright Alsop, of sturdy farming stock, stepped in to rescue the faltering trading house. After giving birth to 10 children, Mary Alsop put the House of Alsop back on firm financial footing. Mary Alsop’s burdens were lightened by the possession of five slaves.

Joseph Alsop’s villa, with its pedimented and columned front, was described by Katherine Mansfield Hubbard, who, in the early years of the last century, remembers the “…beautiful fireplaces, exquisite hand-wrought woodwork and paneling,” and a gracious, carved staircase “…seemingly without any support on its outer side.” She also recalls a conservatory along the west side of the house, where “orange trees and camellias bloomed, giving forth their fragrance.” But more than anything Mrs. Hubbard was struck by the strange and wonderful objects seen about the home, for Captain Alsop “visited many lands and had brought home many treasures.”

The William Cooper House, where generations of sea captains had lived, was also full of exotic objects from distant lands. Facing the wide river at the foot of Court Street, the residence was a study in elegance, a five-bay, gambrel-roofed Georgian dwelling with pedimented windows. Most striking was the front entrance of fluted pilasters and entablature adorned with carved florets. The same exceptional craftsmanship was seen in the rooms, which featured raised and beveled paneling all around. Outside, beautiful gardens on green sloping lawns stretched down to the harbor.

In the 1930s, when the Cooper mansion was photographed for a WPA survey, this fine Georgian home had staked tomato plants growing in the front yard, characteristic of the Italian-American population. Already by the turn of the century, Mrs. Hubbard would lament that the grand dwelling “had been reduced to tenement status.” She preferred to recall when Cooper Lane, as Court Street was known in its seafaring days, “was a place where dwelt people of refinement and culture and note.” Of course, the wealth that produced such elegance came from the ubiquitous slave economy of the sugar islands.

At the Historical Society, in boxes and boxes of shipping records, you can almost smell the briny seaport air mingling with the scents of exotic island products. Here is the brig Mary, which cleared the port of Middletown in April of 1800, bound for the Caribbean. The 75-ton vessel, built across the river in Chatham, measured 62.6 feet along the waterline with a beam of 21 feet. Her owner, Elijah Hubbard, lists a typical West Indies cargo: 1,000 hoops, 2,000 staves, 20 barrels of pork and beef (for plantation slaves), along with a quantity of corn, peas, potatoes and oats. There were also 12 tons of hay to feed the 58 head of cattle Mary carried on her deck.

Cattle and horses were the staple of Yankee exports. The ships were called “horse jockeys.” The animals offered cheap motive power for cane mills on the islands, where waterpower was scarce and windmills more costly to erect. They were precarious cargo, tethered on pitching decks, and newspapers are full of accounts of “stock” being lost in a storm. The brig Mary had no “head” or galley, every inch of space used for cargo.

Elijah Hubbard grew rich in the West Indies trade, founding Middletown’s first bank. Chartered in 1799, it was the oldest in the state. But he lost money on the Mary, which was seized off the islands by French privateers. The sea has its hazards. The brigantine Dolphin, which sailed from Middletown in June of 1787, for Port-au-Prince, fared better. In addition to the usual cargo of cattle, the vessel carried 610 feet of white pine boards and 4,550 bricks from the Mattabesset River, these returning a tidy profit for shipowner Lemuel Storrs.

New England captains usually headed first for Barbados, the farthest to windward; returning, each port of call was a simple run before the trade winds. Sugar, molasses, and rum were the principal imports, but ginger, indigo, pimento, cotton, cacao, coffee and various fruits also were brought back, along with salt from the Turks Islands. Mary Alsop imported mahogany and satinwood, along with sugar and molasses, which was made into rum at the Alsop distillery in Middle Haddam. Local merchants Stephen Clay and Arthur Magill brought back Cuban “segars,” sweetmeats, limes, and pomegranates, while Joseph Wright Alsop, in the 1790s, had a standing notice in the Middlesex Gazette for Jamaican “Pimento by the bag,” pimento being the Spanish word for allspice. Alsop’s principal import was Jamaican rum, sold “by the hogshead or barrel.”

Huge quantities of rum arrived at the port of Middletown. A Customs House ledger for the years 1815?1824 shows vessels loaded with 100 to 125 casks, or “puncheons,” of rum, as much as 15,000 gallons. In 1820, some 165,000 gallons of rum came through the port. Rum was the medium of exchange. J.B. Beers, in the History of Middlesex County, 1884, states that the builders of Middletown’s first Courthouse were paid in West Indian rum, the frame costing 750 gallons. Rum also bought slaves.

Historical Society records show that slaves were brought to Middletown as early as the 1660s. In 1756, Middletown listed 218 slaves in a population of 5,664, every respectable family owning a slave or two; Philip Mortimer had twelve, most toiling at his ropeworks in the North End. A map showing Main Street in the 18th century lists two slave dealers, a Captain Joseph Gleason and a certain Dr. Walker. Also prominent in the trade was Middletown sea captain John Easton, remembered by Connecticut historian George L. Clark as one of “the most successful slave dealers of his time.”

Connecticut outlawed the slave trade in 1788, but many continued to pursue the business. Papers at the Historical Society show Middletown merchants still trafficking in slaves in the late 1790s. A remarkable letter on the trade is found in the Van Deursen correspondence, where instructions are given on the purchase of slaves in the Caribbean. The letter is from a prominent Middletown trading house and addressed to none other than Capt. William Van Deursen.

Capt. Van Deursen, a much-respected shipmaster, represented several Middletown merchant houses, carrying the usual cargo to the islands and back. He also trafficked in slaves. In July of 1798, Van Deursen, master of the shipConcord out of New London, is instructed to proceed to the French island of Martinique, “with all possible dispatch.” Here, he is to sell his cargo, including his ship: “As you shall judge best—if you cannot still sell the ship, you will then vest your property in New Negroes and proceed to Havanah (sic), there dispose of your slaves to best advantage.” Van Deursen, his principals suggest, should also consider selling the “Negroes” on the island of St. Thomas, “always having in mind the grand object of profit, which will be the basis of all your arrangements.”

In 1815, Capt. Van Deursen was appointed to the coveted position of Inspector and Surveyor of the Port of Middletown in an atmosphere of great rancor. Van Deursen had replaced the controversial Alexander Wolcott, whose robust enforcement of Jefferson’s Embargo had made him unpopular with merchants. The Embargo and ensuing War of 1812 was a blow to shipping, but the appointment of Capt. Van Deursen appeared to give merchants a lift. More and more, however, Middletown would see her commerce move to Boston and New York. Times were changing. Sail was giving way to more dependable steam. The year Van Deursen took charge of the port, the steamboat Fulton churned up the Connecticut River, arriving in Middletown with great fanfare.

The grand mansions of High Street, well away from the crowded waterfront, were in the new fashion of detached villas, in their own sylvan setting. These elegant dwellings were built by owners whose shipping fortunes now flowed into manufacturing. The prime example is the pillared Greek revival mansion, designed in 1824 by Ithiel Town for Samuel Russell, whose China trading wealth financed the city’s Russell Manufacturing Company, producers of elastic webbing for men’s suspenders. This shift to industry in the second quarter of the 19th century kept the port of Middletown alive.

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Erik Hesselberg was a longtime newspaper and magazine editor at the Journal Register Company in Connecticut. He is currently working on a book about the lower Connecticut River, from which this story is drawn. He would like to thank Deborah Shapiro, director of the Middlesex County Historical Society, for her valuable assistance.