Presidents and Winchester

Built in 1858 and photographed in the 1930s, the house at 5 Cambridge St. was constructed for Edmund Dwight and his wife Ellen Randolph Coolidge, a great-granddaughter of President Thomas Jefferson. The house is one of several connections between Winchester and presidents’ families or even the presidents themselves.

WINCHESTER – Wherever candidates for the presidency made personal appearances during this last campaign, the list of stumping-grounds did not include Winchester.

Yet, in the past, a few presidents have visited the town or family members have created a connection between Winchester and U.S. presidents.


To go chronologically, 5 Cambridge St. was the home of a great-granddaughter of Thomas Jefferson, and, according to its National Register nomination papers, its design was thought to have been based loosely on the plan for Monticello.

Built on a 12-acre site in 1858, on a hill with a broad expanse of lawn reaching down to the shore of the Upper Mystic Lake, the house was built for wealthy Boston businessman Edmund Dwight (1824-1900) and his wife Ellen Randolph Coolidge (1825-1894), granddaughter of Martha Washington (Jefferson) Randolph.

The house has since had several owners (including mathematician Claude Shannon, considered "the father of information theory") and has been renovated several times. One detail noted in the National Register nomination is the first floor octagonal room which contains a parquet floor said to be laid in a pattern identical to a floor at Monticello.

T. Roosevelt

On Oct. 28, 1884, Theodore Roosevelt came to Winchester to make a speech at the Republican Rally at Lyceum Hall.

At the time, he was 17 years away from becoming president and 16 years from being elected governor of New York. He was just 26 and had hardly any national reputation, being an assemblyman for New York with only two years’ experience in politics.

The Winchester speech came at a significant time in Roosevelt’s career, his entry into the national political scene. That October found him in Massachusetts stumping for the Republican ticket and for Henry Cabot Lodge.

In 1884, the contest for president was between Grover Cleveland and James Blaine. While Roosevelt had opposed Blaine’s nomination and for some months was unwilling to take part in the campaigning, by October he had decided that the party took precedence and so spoke in support of the Republican ticket.

When the election came, Blaine lost by 37 electoral votes. Lodge also lost but in a few years won additional support and represented Massachusetts in the U.S. House of Representatives from 1887 to 1893 and in the Senate from 1893 to 1924. While senator, Lodge was able to work again on party politics with Roosevelt, this time president of the country.


Former President William Howard Taft was more than once a guest of his friend Samuel Elder, one of the town’s most distinguished residents, on Myopia Hill.

On Oct. 10, 1913, “the Common took on a decidedly holiday appearance when about a thousand scholars of the public schools and residents assembled there to greet ex-President Taft.” The party, which also included former Rep. Samuel McCall, was late in motoring to the Common but was greeted with cheers.

“Boys and girls,” Taft said,” it is a great pleasure to meet so many of you this morning and to look into your bright, pleasant faces, your happy, healthy faces….It is not often that I receive such as greeting as this now.”

With just a few words more he was off with a wave of his hat and a smile for the crowd, leaving behind much disappointment that he did not get out to shake hands.

When the country entered World War I, Elder was among the first to fly a new flag from a new pole at his home on Myopia Hill. Taft pulled it to the top in the presence of a small gathering, including then Gov. McCall.

Taft was also present and gave a speech when the Calumet Club (for gentlemen) raised its new flag at 15 Dix St.

Taft made one more war-time appearance, at a patriotic meeting at Town Hall on May 19, when he reportedly urged “the United States, the greatest country in the world, to make for itself a nation of power and strength to support its ideals among all nations.”


During WWI, while Winchester’s Samuel McCall was governor, his lieutenant governor was Calvin Coolidge, who may have visited the McCall home many times.

At least one occasion was documented in the local paper. In May 1916, a senator from Medford invited the entire state senate, the governor, lt. governor, several representatives, and members of the press gallery and attachés to his home for lunch.

Afterward, the entire party, loaded into about 20 automobiles, drove around the Mystic Lakes to the McCall mansion on Myopia Hill. Mrs. McCall and daughters assisted the governor in welcoming them. “The entire house was thrown open” for an informal social time.

The gathering then rode through Stoneham where they visited the Royall House and moved on to the Medford Armory.


Franklin Delano Roosevelt may not have visited Winchester, but his son John was part of the business community prior to the outbreak of World War II.

After graduating from Harvard in 1938, Roosevelt went to work at the Filene's department store in Boston, beginning as a stock clerk in its famous bargain basement.

In March 1940, a new branch of Filene’s opened in the Locatelli Block in Winchester. It was an event for the town and a promotion to assistant manager for Roosevelt.

Though not a resident, young Roosevelt became popular in Winchester. He settled into the mercantile community, joining the Rotary Club and, early in 1941, assisting the Red Cross’s Disaster Preparedness and Relief Committee as chairman of clothing.

Roosevelt resigned his Winchester position in 1941 to enter the Navy. Before leaving, he visited Winchester to say good-bye. At least once during the war, in November 1943, he returned to Winchester while a guest at a Boston Filene’s employees’ rally for the United War Fund campaign.

The Winchester Rotary kept Roosevelt on its list of honorary members for the duration and included him among the Rotarian servicemen to whom they sent gift boxes. However, following the war, the Club had to acknowledge he was a past member.


About 1940, the stable belonging to the estate where Jefferson’s great-granddaughter lived was converted to a dwelling house. Along with a lot of nearly one acre divided between Winchester and Arlington, it was sold as a separate parcel, 9 Cambridge St.

In 1941, this became the home of MIT professor John George Trump (1907-1985), uncle of Donald. That year the country was caught up in World War II during which Dr. Trump was influential in the development of radar and short-wave radar equipment and was appointed director of the British branch of the M.I.T. Radiation Lab.

After the war he remained on the faculty of MIT but also became a co-founder of the High Voltage Engineering Corporation and was associated with the Department of Radiology at the Lahey Clinic.

His many awards included His Majesty's Medal, given by George VI in 1947; the President's Certificate of Merit, presented by President Truman in 1948; the Lamme Medal, awarded in 1960 by the American Institute of Electrical Engineers; and in 1983 the National Medal of Science.

The house on Cambridge Street stayed in the family until 2015. It was the home of Dr. Trump’s son John Gordon (1938-2012). His children sold the house during the year following the death of their mother Gisela (d. 2014), who had moved to Myopia Road.

Neighborhood word of mouth has it that Dr. Trump’s nephew was a visitor at the Winchester house, even making a helicopter landing, though he was not a presence in the community.

There may be other presidential connections. In 1972, the Boston Globe reported that a rumor was making the rounds in town that Jacqueline Kennedy Onassis might be seeking a secluded home in Winchester for part-time living. The rumor re-emerged in more recent years that she may have lived on Myopia Hill, though there is no confirmation.

Any further information about presidential connections would be gratefully received at the Archival Center.

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