Independence Day is the annual celebration of America’s birthday — and so, on Martha’s Vineyard, it seems fitting that an innately American sport goes to bat each year on the Fourth of July.
While the whole Island will be focused on the 250th anniversary of the signing of the Declaration of Independence, the Island also has a 100th anniversary to mark in Chilmark at Flanders Field, at one of the oldest pickup softball games in the country. So Sunday morning, at the small diamond on Peaked Hill, the century-long tradition will continue as players arrive and — at the call of “Gloves in!” — throw their gloves in a pile to be randomly separated into teams.
To understand the start of this tradition, travel back 100 years ago to the Roaring Twenties, which would soon collapse into the Great Depression. The Island population back then was under 5,000, and by the early 1930s, one-third of the population was on some form of government relief under Roosevelt’s New Deal.
In this uncertain and relatively idle time, people pulled together for Sunday gatherings, and a game called softball was just becoming popular. The lore is that the game was invented in 1887 on Thanksgiving Day, when a Princeton student rolled up a boxing glove and threw it at a Harvard student, who hit it with a broomstick. Softball, sometimes called “indoor baseball,” was born. It became a way to keep baseball skills sharp through the winter. The game officially adopted the name “softball” in 1926, and it grew in popularity throughout the 1930s.
During the early years of its history, the Chilmark softball game was established in the backyard of the Flanders family in Menemsha as a Sunday morning neighborhood pickup game. Following church services, families would gather, choose sides, and play until lunchtime. When the game outgrew the Flanders’ backyard, it wound up in Muriel Toomey’s expansive yard off the road to Gay Head, now Aquinnah.
Fast-forward half a century to the mid-1980s. Toomey’s field was sold; the diamond moved to the softball field of the West Tisbury School, and then to behind the West Tisbury fire station. Here it remained for a decade.
During this time, photographer Peter Simon took on the unofficial role of softball manager. He and Jim Brooks, team captains, would choose sides. This was known as “the Era of the Chosen.”
It was in 1984 that this writer first started playing. By the seventh inning of my first game, I was hooked. Those games were serious and competitive — or so it seemed until the kibitzing began. There were arguments about everything. Sometimes the arguments almost took over the game.
But Bill Edison, the longtime commissioner, would stop the game when the quarreling got out of hand and consistently remind everyone, “Time is running short — play the game! Summer is fleeting.”
Around 2002, the game moved back to Chilmark, to a field off Peaked Hill Road. This was accomplished through the efforts of longtime players David Flanders, Billy Meegan, and Peter Simon, and of course Edison, among others. Some of these legends have sadly passed on, but their spirit remains, and the game remains, too — with opening day set, as always, for the Fourth of July. Those who have passed on are typically honored, as they were last Sunday at an informal gathering of the old guard for a practice game prior to the July 4 opener. There were fond words of remembrance for Jay Grossman, a longtime player who passed away in March after a battle with cancer.
Once the game was moved back to Chilmark, it took on a gentler and much-improved culture. Longstanding player Jason Balaban remarks, “Although we were all trying our best, there was always something larger than wins and losses. Comradery, friendships, history, dreams were all being formed or played out in this universal summer game. It was and still is an instrument transmitting and transferring us to our childhoods. There’s a reverence for the simple act of playing ball on a field with friends.”
On July 5, 2009, the field was dedicated as Flanders Field, in memory of legendary Chilmark player David Flanders, who had died the year before. Hans Solmssen, our oldest player at 89, reflects on Flanders as one of the true founding fathers of the game: “What I vividly remember is David Flanders stepping up to bat. All the infielders would drop their gloves, because we knew David would drive the ball into the pine trees for a home run.”
Although there is no official dugout, there is a large players’ bench: the Tony Horwitz Honorary Bench, a tribute to the late Pulitzer-prizewinning author who was one of our most enthusiastic players, as well as the in-game scribe.
Chilmark softball may not have had Babe Ruth visit, but still, it has a storied history. One of the more searing memories is of Hall of Famer Jackie Robinson, who attended one game back in the early ’60s. In the ninth inning, with men on base, Bob Crichton stepped back from the plate and announced, “Now batting for Crichton, Jack R. Robinson.” He handed the nearly blind Robinson his bat and stepped away. Robinson fondled the bat and peered out toward the pitcher. He clearly wanted to give it a try, but then he handed the bat back. What followed was the silence of respect that no one else was ever accorded on the field.
Edison’s most profound contribution to the re-establishment of the game in Chilmark was the promotion of friendships, good sportsmanship, and high-spirited fun. Paul Iantosca recalled taking his son-in-law to the game, assuming he himself would just watch it. But “everyone was warm and welcoming. I watched players from 14 to 84 just out on the field having an inordinate amount of fun and laughter. Everyone was enjoying the game as if they were kids again. I was hooked, and threw my glove into the pile for the second game. What I realized as the morning progressed was that I was amid a group of the kindest and warmest people I had ever experienced.”
At the end of the day, what makes this game so special is the spirit that has developed but which remains similar in its formula to those early days almost a hundred years ago. It’s about families — moms and sons and dads and daughters. It’s a social event where friendships have formed and exuberance and joy accompany a well-played game. It’s the game of summer.
Players have come and gone. The famous, the not-so-famous, the year-round Islanders and the summer folks. Hedge-fund founders and hedge trimmers, fishermen, artists, writers, carpenters, architects, teachers, doctors, lawyers, psychiatrists, surgeons, pilots, writers, poets, photographers. Moms and sons and dads and daughters. All playing a game that has no clock. It’s the timeless game, and we’re all just kids again.
Heading out to Peaked Hill on Sunday mornings this summer, we will recite the resonant words of Bill Edison: “Time is running short — play the game! Summer is fleeting.”
Retired psychotherapist Sig Van Raan has been playing Chilmark softball since 1984. He has three grown children and a growing brood of grandchildren, who are regular visitors to his home in West Tisbury, where he lives with his wife, Susan Dickler. A longer version of this story was previously published in Arts & Ideas 2026 and can be read here.