Exploring JFK's Brookline - Another Kennedy Pilgrimage

Ten days ago, on October 4, was the birthday of Joseph P. Kennedy III, former representative of the Fourth District of Massachusetts in the United States Congress. He is the grandson of former Attorney General and New York Senator Robert F. Kennedy (1925–1968), grandnephew of President John F. Kennedy (1917–1963), Massachusetts Senator Edward M. Kennedy (1932–2009), and Ambassador Jean Kennedy Smith (1928–2020). I met him nine years ago at a forum at the John F. Kennedy Presidential Library and Museum. He was very kind to me, and I wish I had more time to interact with him. Today, he serves as Special Envoy to Northern Ireland for Economic Affairs.

It seemed fitting, then, that on October 14—ten days after his birthday—I should return to Brookline to visit sites connected to his family. I had been here once before, on August 12, to see the Kennedy birthplace, but this time I wanted to remain within Brookline itself and visit four places, all within walking distance. Each would be seen only from outside, early in the morning, so as not to disturb the quiet neighborhood.

I woke up earlier than planned and decided this was the perfect day to go. After an early breakfast, I printed out directions and left the house at 5:43 a.m. The air was cool at 47 degrees, and the streets were still dark.

I boarded the bus to Wellington Station at 5:46, then transferred to the subway at 6:01. For the next twenty-six minutes, I read from JFK: Coming of Age in the American Century, 1917–1956 by Fredrik Logevall. It felt appropriate to be learning about Kennedy’s youth while traveling to the places where he grew up.

At 6:30 I exited Roxbury Crossing, where daybreak had just begun. The rising light silhouetted the Islamic Center of New England, a striking sight that made me think of distant lands I may never visit. Duke Ellington’s “Arabesque Cookie” played in my mind, recalling a scene from Malcolm X (1992) where Malcolm makes his pilgrimage to Mecca.

At 6:44 the number 66 bus arrived, only slightly late. Twelve minutes later, I reached my first destination: the Florida Ruffin Ridley School at 345 Harvard Street, formerly the Edward Devotion School.

According to the National Park Service, this was where “from kindergarten through third grade, John F. Kennedy attended his local public school.” The school had a strong academic reputation, and Rose Kennedy wanted her children to grow up alongside neighborhood friends.

As a student, Jack was bright but often distracted. One teacher recalled his habit of daydreaming in class. Once, when the teacher planned to tell Rose about it, Jack sprinted home ahead of her to defend himself, saying: “You know, I’m getting on all right, and if you study too much, you’re liable to go crazy.”

Today, students at the school continue to honor Kennedy’s memory by studying his legacy in third grade. Standing outside the building where his early education began, I could almost picture the boy who would one day become president.

From there I walked ten minutes along quiet neighborhood streets to my second site: St. Aidan’s Church and Rectory.

Built in 1911, St. Aidan’s was Brookline’s third Catholic parish and central to the Kennedy family’s life during their years in town. John Fitzgerald Kennedy was baptized here on June 19, 1917. Though the building was converted into housing in 1999, the original architecture remains striking.

I walked carefully, aware that it is now private property, but lingered to admire the design. I imagined Joe and Rose Kennedy walking up those very steps with their children for Sunday Mass or baptisms. It was moving to stand where such milestones in the family’s life once took place. 

I next sought the Kennedys’ second Brookline home, located at 51 Abbottsford Road. 

After briefly losing my way, I found it at last. Without a marker to indicate its importance, it would be easy to miss. Out of respect for the residents, I took only a few photos before leaving.

The National Park Service records that the family moved here in 1920 as they grew to include Eunice, Patricia, and Robert. Joe Sr. was then a young bank president and film industry investor. Rose loved the wraparound porch, where she could watch the children play, sometimes dividing it into sections so each child had space of their own. She also encouraged them to read clippings from the bulletin board she kept, preparing them for spirited debates at the dinner table.

The family lived here until 1927, when Joe decided to move them to New York, convinced that Boston was “no place to raise an Irish family.”

Finally, I returned to 83 Beals Street, the Kennedy birthplace and now the John Fitzgerald Kennedy National Historic Site.

When I last visited, the property was fenced off. This time, the fence was gone, the house renovated, and a sign announced that tours would resume on October 19. I resolved to return soon for an inside visit. 

Though I had seen the house before, standing there again felt like closing the circle of my Brookline pilgrimage. To walk where history unfolded, even quietly on a suburban street, is always a moment of awe.

Although my pilgrimage in Brookline was supposed to take less than half an hour to accomplish, it took me fifty-two minutes to complete my sojourn here. To walk where the past walked. To know that things happened here that history has recorded is a thing of awe and wonder.

I walked up Harvard Street and waited for the number 66 bus arrive, which it did about 8:12. I got onboard and after sixteen minutes of waiting, I got off the bus stop located at JFK Street and Eliot Street in Cambridge, near Harvard University. I was going to begin another pilgrimage for President Franklin Delano Roosevelt, who stayed at Adams House as an undergraduate student in the early 1900s. However, there was construction around the site, so I decided to return next year in 2024 to accomplish this new pilgrimage.

My pilgrimage to Brookline was completed, but there was one more task I wanted to finish. I decided to go to Mount Auburn Cemetery to pay my respects once again at the final resting place of Arthur Meier Schlesinger Jr., among the most famous historians of his time and had known President John F. Kennedy since his time in Harvard. 

Though my pilgrimage to Brookline was complete, I wanted to end the morning by honoring one more figure connected to Kennedy: historian Arthur M. Schlesinger Jr.

At 8:52 I arrived at Mount Auburn Cemetery. As I walked along the paths, I heard singing “Ave Maria,” clear and beautiful, from a woman practicing for a funeral. For a moment I felt like Prince Philip in Sleeping Beauty, following an unseen voice through the woods. When she noticed me listening, I apologized, and she kindly explained. It was a fleeting but memorable encounter.

At 9:15 I reached Schlesinger’s grave, where I sat for nearly an hour, reflecting and photographing three of his books I had brought with me. 

 Though his birthday would be the next day, October 15, this visit felt like a fitting conclusion to the day’s pilgrimage.

As I thought about how to close this entry, I realized that October 14 was also the birthday of Dwight David Eisenhower: general, commander, and the 34th President of the United States. Though Arthur Schlesinger did not hold Eisenhower in the same regard as Kennedy, the two presidents were connected in history. Eisenhower’s words to students at Grinnell College in 1965 echo Kennedy’s own call to service, making them a fitting conclusion for today:

“All around you at this moment are problems that arouse in you an ardent wish that you might participate directly and actively in their solution. Your idealism and enthusiasm for justice seem to require of you some personal and public proof of their existence within you. This is entirely natural and laudable. And I, for one, would never attempt to quench or even to dampen the ardor of youth. But I would point out to you that in the long years ahead, countless calls will be made upon you for a deep and sympathetic understanding, a thorough knowledge and a generous wisdom of what America is and what it should be… By no means, in so speaking, do I advocate a do-nothing attitude about current public affairs. I only urge that now you ready yourselves to help solve the nation’s inevitable and sometimes dismaying problems of your time.”