Here are three short sports entries from the early years of the 20th century. The first has a high school hockey game played at Jamaica pond. Hockey, on the pond? Hmmm... It took me a while to sort this one out. I suspect that the game was played at the pond, not on the pond. At the time, the city would flood playgrounds and set up rinks for skating, as the second entry shows. I think we can assume that the hockey game was played on the field on Perkins street opposite Ward's pond, and not on the pond itself.
[Addendum: Apparently, hockey was played on Jamaica Pond. Here's an exerpt from from a book published in 1906.
"Jamaica Pond was, far and away, the favorite and fashionable skating ground. Here, almost any afternoon or evening, when the ice was good, could be seen hundreds of skaters. Skating parties of Boston's elite were formed for visiting the pond, both by day and on moonlight evenings, and this custom remained popular for years. Here also was the boy's paradise for ice hockey; the boys frequently lined up fifty or more strong on a side, and the constant "mix-ups" that occurred, in which a hundred or more hockeys were flying about in reckless confusion, gave onlookers the decided impression that "something was doing." Surely those of us now living who took part in them will feel our pulses beat a trifle quicker as we recall those hard fought contests on Jamaica Pond." Source: Old Boston Boys and the Games They Played. ]
The third entry shows that curling was being played locally one hundred years ago. There were many Canadian immigrants in Boston at the time, so it makes sense. Before the building of indoor rinks, the Globe reported on natural ice conditions through the winter, with news from Fresh pond, Scarboro, Jamaica, and the rest of the metropolitan Boston ponds. Winter weather was significantly colder at the time, and Boston seemed to be in love with skating and ice sports. Some ice was reserved for school hockey, some used by amateur club teams, and apparently the curling fans were able to reserve Scarboro pond for their special use.
Boston Daily Globe January 18, 1902
Brookline H.S. 2, Boston Latin 1.
One of the closest and most exciting hockey games played in this vicinity this season was that yesterday afternoon between Boston Latin and Brookline high schools in the Preparatory school league series at Jamaica pond, which was won by Brookline, 2 to 1.
[a short description of the game follows]
Local Skating Bulletin.
Skating in Boston and suburbs is generally good. The Boston park commissioners issue the following bulletin on the condition of the ice:
Jamaica Pond, good.
Wood Island park, East Boston, good.
Billings field, good.
Columbus-av playground, good.
Roslindale playground, good.
First-st playground, South Boston, good.
Gibson playground, fair.
Nepoonset playground, fair.
Charlestown playground, good.
North Brighton playground, excellent.
Scarboro pond, Franklin park, good.
Franklin field, no skating.
December 3, 1903
Season Opened with Two Contests on Scarboro Pond, Franklin Park.
The Boston Curling club opened the season yesterday afternoon with two matches played on the ice at Scarboro pond, Franklin park. The rinks were skipped by Messers Renton, Weymss, McGaw and J.Cairns. Renton's team defeated Weymss' 21 to 11, and McGaw's quartet won from Cairns' 21 to 17.
[finished with scoring results]