Back in the day — the day when ladies were admitted to the Westport Y only after ringing the doorbell at a small entrance on Main Street (and even then they were allowed only into a small knitting room) — men swam naked in the pool.
It took a while to break the habit, after women received full membership. Men routinely walked out of the locker room nude. Their saunters were interrupted by females, who were no doubt delighted surprised at the perks their new membership brought.
That’s the kind of tale that gets told at Ambassador Club meetings.
Once a year, the Westport Weston Family Y honors its Ambassadors — anyone who has been a Y member for 25 years or more — with a lunch. The food is one draw, but story-swapping is much more important.

The original Westport YMCA -- now called the Bedford Building.
This year’s event — the 4th annual — is set for Thursday (Sept. 16), 12 noon in the Bedford Room. (Many Ambassadors remember when that room — in the building of the same name — was the true center of the Y. Some may even remember Edward T. Bedford, the local philanthropist who founded the Y in 1923.)
The luncheon draws around 100 people a year — men and women.
All are fully clothed.
(If you have been a member of the Y — any Y, actually — for at least 25 years, and want to attend the lunch, contact Joan Vitali by phone at 203-226-8981, ext. 178, or email: jvitali@westporty.org.)
Interesting piece. I have been a member of the YMCA, off and on, since 1953 and it was really a hub then of kids in the afternoon and then a very gentlemen’s -like -club at night. The first floor was reserved for billards room for adults only. There were Friday night dances there for us teenagers and were a big attraction. And who can forget Ms. Comer’s dance classes, complete with white gloves and suits for us boys, in the gym upstairs. I don’t recall many girls being allowed in the gym, pool-ping pong table area, pool or elsewhere. Yet, I also don’t remember men walking around naked either. Unfortunate for the women, however. My mother found great gender discrimination as a member of Patterson Club back then as well, even though she could handily beat most of the male members (including my father who took so much ribbing that he left to join Waterbury CC). So I guess you don’t have to catch an episode of “Mad Men” or read your illustration here to know that women have come a long way. About time. Maybe some time soon, we can put one in the White House as President (sorry Sarah, too much of a pay cut for you).
I’m not aware of being able to stroll freely au natural at the Y back then but I’m well aware of the sign inside the Sherwood Island bathhouse sternly reminding beach goers to wear their bathing attire while showering. How ironic.