In 1744, Dr. Alexander Hamilton took a long trip to New England for his health. Given the rigors of travel in those days, it may have been a poor choice.
Alexander Hamilton was a Scottish doctor who immigrated to Annapolis, Md., where he practiced medicine. In 1744, he had yet to marry, and he included sharp observations about women in a diary of his travels. Newport, R.I., he noticed, was as ‘remarkable for pretty women as Albany is for ugly ones.’
He published his lively and opinionated travel diary in a book, a rare account of colonial American life between 1730 and 1745. He was especially impressed by a colonial womanizer who showed him the trophies he collected from the ladies.
Alexander Hamilton Takes Off
Alexander Hamilton left Annapolis on May 30, and traveled by boat and horseback with his African-American slave, Dromo, and occasional traveling companions.
They journeyed through Delaware, Philadelphia, New Jersey, New York City, up the Hudson to Albany and then back down. Hamilton and Dromo then ferried from Long Island to New London and Stonington in Connecticut and on to Rhode Island. They spent a night in Kingstown, R.I., at a public house run by a man named Case – ‘a talkative, prating man,’ according to Hamilton.
On July 16, Alexander Hamilton recorded in his Itinerarium his visit to Newport, R.I. Some of the things he describes still stand: the White Horse Tavern, the Old Colony House (which he calls the Town-House) and Trinity Church (which he calls the Church of England).
Alexander Hamilton wrote that they set off from Case’s tavern in Kingstowne, R.I., at 6:30 am on Monday, July 16. On the ferry ride, he noticed an island called Dutch Island because the Dutch had once settled it.
As they stepped into the ferry boat some stones lay in her bottom, which made it hard for the horses to get in. Alexander Hamilton wrote,
Dromo desired the skipper to “trow away his stones, de horse be better ballast.” “No,” says the fellow, “I cannot part with my stones yet; they will serve for a good use at another time.”
Alexander Hamilton described Newport as a ‘pleasant, open spot of land, being an entire garden of farms,’ about 13 miles long and five miles wide.
The town itself then consisted of one straight, narrow street, with several lanes going from it on both sides.
Hamilton listed one large Market House, the Town House (‘a handsome brick edifice’), two Presbyterian meetings, one large Quaker meeting, one Anabaptist, and one Church of England, with a fine organ and a clock on the steeple.
Hamilton then went down to see the fort, a square brick and fort building on an island in the harbor.
“This place is famous for privateering,” wrote Alexander Hamilton. “They had about this time brought in several prizes, among which was a large Spanish snow near 200 tons burden, which I saw in the harbor, with her bowsprit shot off.”
Alexander Hamilton had an eye for the ladies. In Newport, he wrote, ‘This town is as remarkable for pretty women as Albany is for ugly ones, many of whom one may see sitting in the shops in passing along the street.’
He had lunch at the White Horse Tavern, and in the afternoon his friend Dr. Moffatt showed him around town. Moffatt was probably Dr. Thomas Moffat, a Loyalist whose house was destroyed by rioters in 1765.
Moffatt then took Hamilton to see the painter Robert Feke and look at his work. Today the Redwood Library and Athenaeum exhibits one of his portraits.
Alexander Hamilton described Feke as, ‘the most extraordinary genius ever I knew,’ because he captured likenesses without taking any lessons.
Feke looked exactly like a painter, wrote Hamilton, ‘having a long pale face, sharp nose, large eyes,– with which he looked upon you steadfastly, –long curled black hair, a delicate white hand, and long fingers.’
Cabinet of Curiosities
Alexander Hamilton enjoyed society, and had entrée to the elite circles wherever he “traveled.
That evening he and Moffatt spent an agreeable visit with Dr. Keith, ‘another countryman and acquaintance’ and Dr. Brett, ‘a very facetious old man.’
“I soon found that Keith passed for a man of great gallantry here, being frequently visited by the young ladies in town, who are generally very airy and frolicsome,” wrote Hamilton. “He showed me a drawer full of the trophies of the fair, which he called his cabinet of curiosities. They consisted of torn fans, fragments of gloves, shims, snuff-boxes, girdles, apron strings, laced shoes and shoe-heels, pin-cushions, hussifs, and a deal of others such trumpery.”
Alexander Hamilton wrote that he spent the night at Dr. Moffatt’s, thinking, no doubt, about Dr. Keith’s cabinet of curiosities.
Photos of buildings courtesy Library of Congress. Portrait courtesy Brooklyn Museum, 43.229_SL1.jpg. Licensed under Public domain via Wikimedia Commons. “SusannahBoutineau” by Robert Feke ( – Nova Scotia Museum. Licensed under Public domain via Wikimedia Commons. This story bout the other Alexander Hamilton was updated in 2021.