Chilmark softball players team up on summer Sundays

The Chilmark Softball League has been a hit for 87 years.


It was one of a long string of sparkling Sunday mornings this summer as I drove down Tabor House Road in Chilmark, took a left on Pasture Road onto a dirt road, headed up past a sign that said, “Slow Mice,” and in the distance I could see about 10 cars parked on the side of the road. I was told the game would start at about 8 or 8:30 am, but as I passed the parked cars and looked at the field cut out of the woods on the left it was 8 o’clock sharp and there were about 15 or 20 more cars parked adjacent to the diamond and a game was already well underway. These people love their softball. 

The field was serviceable enough but not without its share of idiosyncrasies. It was 225 feet to the high grass in left and about 240 to the grass and a road in right field. The outfield had a swale that must have tripped up many a fielder over the years, and there was enough stray gravel on the ground to leave a mark. “But as a rule,” Sig Van Raan, a Chilmark softball regular, said, “not a bad field at all.”

On the first base foul line is a scoreboard with a plaque dedicating “Flanders Field” to the legendary batsman and originator of the Chilmark Softball League, David Flanders. Flanders began the league in 1932 as largely a family league played on the back fields of Menemsha, but after several years the game increased in popularity and migrated over to Toomey Field in Chilmark, roughly across from Chilmark Chocolates. During the 1940s, the game, while always welcoming to all, became more of a male-oriented affair and more competitive. And heading the list of alpha players was none other than David Flanders. 

Eighty-two-year-old Hans Solmesson, who still plays today, remembers when Flanders terrorized the league with his mighty bat. “Flanders pretty much hit a home run every time he stepped up to the plate,” Solmesson said. “We’d all stand in the outfield with our hands by our sides and watch the ball sail over our heads.” 

Ultimately, the long ball may have led to the demise of Toomey field; in the 1980s the field was sold, and because the neighbors were tired of having outfielders chasing down fly balls in their backyards, the league was asked to vacate. 

In 1985, the Chilmark Softball League was forced to move — God forbid — to West Tisbuy. 

Longtime league player and Vineyard photographer Peter Simon arranged to have the games played behind the West Tisbury Elementary School and later on the field next to the West Tisbury firehouse but finally in 2001, the game returned to what is now Flanders Field in Chilmark, back to its roots. Instrumental to bringing the game back home were longtime Chilmarker Billy Meegan and the legendary BIll Edison. 

Edison was a former teacher, Chilmark Community Center councilor, and heir to the Edison retail empire, but as Sig Van Raan wrote in his obituary for the MV Times, Edison had strong Bohemian creds as well.

“Bill (had a) long-standing friendship with Lawrence Ferlinghetti and (an) affinity for the San Francisco era of the ‘50s and ‘60s Beat Generation. Bill served as a part-time bartender at El Matador, San Francisco’s infamous bar frequented by the great writers and jazz artists of that time. He got to know Kerouac and Saroyan as well as Ginsburg, who read his poem ‘Howl’ there one night.”

Edison was 90 when he passed away in 2018. “He was a lovely guy, a true champion of the game,” Caleb Caldwell, a league regular, said. “Even after he stopped playing, he’d pull up in his beat-up Volvo, pull out his lawn chair and smoke his pipe, he was such a fixture.” 

But Edison will be most remembered to Chilmark softball for the personal stamp he put on the league. 

“Bill reinstituted the game here,” Van Raan said, “he announced the formation of the position of the Chilmark commissioner of softball … and he became it.” He said there would be no rules and “don’t ask me to mediate anything … just play fair, be nice, and have fun.”

Over time, Edison became commissioner emeritus and passed the reins of commissioner to Sig Van Raan, Caleb Caldwell, and Hans Solmssen.   

“I’m an agnostic and this is church for me,” Caldwell said.

At 82 years of age, Hans Solmssen is a gentleman and a graceful athlete. In the game I watched, Solmssen seemed indefatigable, pitching both games of a double header. 

“The game has become a wonderful institution thanks to Bill Edison,” Van Raan said. “It can be competitive but in a very friendly way, not like the old days … the players range in age from 8 years old to guys in their 80s.”

Each game begins with a ritual called “Gloves In.” Players throw their gloves into a pile and one of the kids pulls out the gloves and puts them into two piles thus assuring an egalitarian choice of teams. 

The game runs itself on the honor system — there are no umpires, the balls and strikes are called by the catcher but, as Caleb Caldwell says, you can’t really strike out, you can stay up as long as you want until you hit the ball. If there are any issues, theoretically the commissioners will settle them but they try to stay out of the way. 

Van Raan explains that there are some local ground rules to contend with. If you hit a fly that’s not caught, you get to go as far as you can without being thrown out — however, if it rolls into the weeds it’s a ground-rule double. If the ball hits the road on the fly it’s a called a Kerouac (On The Road) and it’s an automatic double. Over the road, it’s a home run.

If you hit five foul balls in a row it’s considered a strike out. If a pitcher throws six straight bad pitches it’s an automatic walk. “But most guys think it’s nerdy to walk so they’ll swing at the bad pitches to avoid having to take the walk. I think in the three years since that rule was instituted, I’m the only guy to elect a walk,” Van Raan said. 

There’s also the matter of Tashmoo, Ed Eger’s big lab that was lying just off the first base line the whole time I was there. I’m told he’s also likely to pass out on the playing field, in which case it’s “let sleeping dogs lie.”

“There was a time when we had umps, in fact one of our more famous umps was blind Rabbi Weiz,” Van Raan said. “He was in his 80s and had an odd strike zone, there was virtually no limit to how high a strike could be. That’s why we called him the blind rabbi. But nobody dismissed him, we all really liked him.” 

In fact, a feeling of good sportsmanship and camaraderie prevails at Chilmark softball games. 

“If some guy who may not be the best player makes a good play,” Van Raan says, “he gets an ovation as he walks off the field. It’s a great moment.”

Another thing that makes the Chilmark Softball League unique is the fact that it’s intergenerational. The game I watched had seven father/son, father/daughter, grandfather/grandson combinations playing. 

Perhaps this aspect is best exemplified by the Balaban family of Chilmark and New Jersey. Fifteen-year-old Sophie Balaban was the “Gloves-In” girl for our game. She said she grew up running a lemonade stand on the sidelines. When she was 2 or 3 her father would hold her while playing third base. Sophie’s father Jason has played since he was a kid, and her grandfather, Dan, played from the time he was 16 until he was 90. Sophie’s uncle and cousins play as well, “I’m addicted to the game,” Sophie says, “I’ve been a part of it all my life.”

This has been a tough year for the Chilmark Softball League, it lost two of it’s most beloved members over the winter: Peter Simon and Tony Horwitz. Horwitz was a Pulitzer Prize-winning reporter and bestselling author but Caleb Caldwell remembers him as a center fielder. “Tony had this wonderful, zany, goofy sense of humor. He was a kid and he made all of us be kids again,” Caldwell said. “Softball was so much a part of his life.” After the games Horwitz would write up a synopsis of the games and circulate it to all the players, “Half the time he’d just make the shit up,” Caldwell said.

“Tony set the gold standard for popping it up,” Van Raan said, “and then he’d turn to the bench and say in a talmudic supplication, ‘Why did I swing at that?’” 

Rabbi Jonathan Lipnick was Horwitz’s batting coach. “I just had to laugh at the fact that anyone in this league would have a batting coach,” Lipnick said. “Did I do any good — probably not, but after about five years Tony got me a T shirt with ‘The Hebrew Hammer’ printed on the front, and I’ve been wearing it this year in his memory because I miss him so much.” 

Peter Simon was also an integral part of the game for years. “I’ll always remember him racing around barefoot,” Van Raan said, “and I guess he’ll also be remembered for the day he brought Dodgers great, Jackie Robinson to play.” Simon, whose family and the Robinsons were friends, invited Robinson to play, unbeknownst to the other players, leading Hans Solmesson, who was pitching at the time, to do a world-class double take when Robinson came up to bat. 

“There have been other celebrities at the games as well,” Van Raan said. “Spike Lee played for a season a few years back, he used to show up in a Yankees uniform and cleats. He even got an unassisted triple play.” Apparently Lee was playing shortstop and caught the ball on the fly and tagged the runner out and then ran down the guy at first. “Sometimes I’ll see him at Jet Blue,” Van Raan said, “and I’ll give him the three finger sign — triple play!”

Sig Van Raan ran over to me after the game and said, “Walk-off homerun — 6-5 — this was a really great game!” Yes, as scores go it was a good game, but games at the Chilmark Softball League are measured as much by tradition, camaraderie, humor — by grandfathers playing ball with their grandsons and lazy labs lounging on the infield as they are by walk-off home runs in the ninth. That’s the way the game is played in Chilmark.


  1. Thanks for the kind words about my dad Bill Edison & I wish he were here to laud the passing of Tony & Peter. Toomey’s Lot deserves its own opus: toe bones were broken & sports careers challenged on that stony, poison ivy ridden, pine needled “field,” and woe betide center fielders grappling with a sloping uphill. Scores were kept in the sand and easily eradicated by Peter Simon’s dog. My favorite sound was “ketong!” —a foul ball hitting rusty truck hoods in the lot behind us. All hail those who survived Toomey! I am sure battled tested souls at Peaked Hill have storied scars.

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