The Boys of Summer – Weston Little League Hits Silver Anniversary, Announces Summer Baseball Plans

Weston Williamsport team, 2019

Weston Little League celebrates its silver anniversary, 25 years of all the fun you can have with a bat and ball. And this year, the Boys of Summer are ALL ON, with options for grades 1 & 2, all the way up to 15 and 16 year old competitive baseball. And yes, “Boys” of summer is purposeful as there are no options for girls in the summer, a situation that has been true for several years–there simply hasn’t been interest.

The Owl has a soft spot (feather?) for Little League–if I were positive that JP over there at Weston Soccer weren’t reading this, I would say quietly very very quietly…it’s my favorite youth program! There, I’ve said it–come and find me–I’ve got a nice bat signed by someone I can’t remember on the Red Sox. Why is it the favorite? An absolutely amazing and inclusive crowd of parent volunteers, and kids who cheer for each other all the time, because let’s face it, baseball is a whole lot of sitting on a bench–might as well cheer, no?

Who needs an Owl story about this? You do. Or just click the close window, I don’t care. The Owl family moved here when the kids were in second grade–from Brazil where I can sum up baseball as not a sport. Nothing is apparently a sport except the one with a black and white ball. Anyway, an Owlet made a bestie here who played baseball (and his dad was a former Weston high school baseball player and current coach) and hockey. The Owlet wanted to be with his bestie. Let us kindly call Owlet’s attempts at hockey or even staying up on top of ice as ummmm…less than fruitful and perhaps painful. Baseball was better.

Put me in coach…I’m ready to play…today (John Fogerty of course. Not the first base coach)

The Owlet’s bestie and his father convinced the Brazilian to join Little League in 4th grade. Go Cubs. Oh wait, it was Indians first. He struck out for five games straight. Then a friend accidentally beaned him with a pitch, the Owlet got to first base, stole second, and then the rest was history. Fifth and sixth grades on the Cubs…and then with the help of that father and a few other fathers (even those on other teams), the Owlet made the Williamsport team as a sixth grader–the pinnacle of baseball-osity. And it was fun. Now he plays club baseball– or he would if he weren’t injured from the sport with a black-and-white ball. And the Owl is thankful to a great group of volunteers and snack shack hot dogs for making life in Weston a little bit more American.

This year’s Williamsport team has been selected and the Owl wil be following their exciting drive for the World Series. Go ‘cats!

If you have a kid new to baseball or new-ish to baseball, or who knows? Maybe a David Ortiz in the making–check out the options for your kid this summer.


JIMMY FUND “ROOKIE” LEAGUE (Current Grades 1 & 2):
This is designed to be more of a recre­ational league. There are no weekend games. Season is typically 5 weeks, on Wednesdays, starting the week of 7/6. Games are against neighboring towns – Wayland, Lincoln/Sudbury, Assabet Valley. Players will use Spring 2021 Jerseys.

(Players have just finished grades 1 & 2 grade in June 2021) 

JIMMY FUND LEAGUE (Current Grades 3, 4, 5, 6):
This is designed to more of a recreational league. There are NO weekend games. Season is typically 4 weeks with a short playoff for qualifying teams. Grades 5 & 6 will play on a 70’ diamond and grades 3 & 4 will play on a 60’ diamond.
Games are against neighboring towns (Wayland, Lincoln/Sudbury, Assabet Valley)

Minor League: Current grades 3 & 4 – Games: Monday, Wednesday & every other Friday night.

Major League: Current grades 5 & 6. Intermediate diamond & full baseball rules

Players in both leagues will be issued uniform jerseys & hats

Sponsoring Weston teams in all the divisions above or at all will be contingent upon demand and enlisting a coach. Little League is looking for coaches for each of the divisions above. If you can help, please email:

BAY STATE LEAGUE (9 – 12yrs):
This is the most competitive that Weston offers for the summer besides Williamsport. 12 year olds and some 11 year olds will play on a 70’ diamond (“A” Division) and play full baseball rules. Our 11 & 10 year old team (“B” Division) plays on a 60’ diamond and follows Little League rules. We are hoping to have a 9 & 10 year old team as well (“C” Division).

There are weekday AND weekend games. Games are played in towns all over Eastern MA. Season starts in late June and after a few weeks, teams are reseeded and the season continues until the 2nd week of August.

Sponsoring Weston teams in all the divisions above or at all will be contingent upon demand and enlisting a coach. We are looking for coaches for each of the divisions above. If you can help, please email:

Players will be issued uniform jerseys and hats. 

The Lou Tompkins All-Star Baseball League runs a competitive big-diamond summer baseball season for players ages 13-16. Over 50+ teams from Northeastern Massachusetts compete in over 18 games ending the regular season with a Tournament of Champions. The season runs from mid-June through July with playoffs the first week in August.

This summer, Weston & Wellesley Little Leagues are combining to create more competitive rosters and experiences at all Lou Tompkins levels. Based on past enrollments, Wellesley/Weston will be entering teams in each of the age/grade divisions (LTA, LTB & LTC). All teams will be coached by professional baseball coaches.

Players who play AAU/Club, Middle or High School baseball are encouraged to register. Teams will have weekly practices and games are played during the week and every other weekend. The divisions are structured so there is less travel than prior years. Email: with any questions.

See the Weston Little League page for more information.

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