Friday Flashback #322

The Apple Festival has been gone now far longer than it ran.

But for 18 years — from 1982 to 1999 — it was one of the highlights of autumn in Westport.

Conceived by Staples High School PTA leader (and, later, 2nd Selectwoman) Betty Lou Cummings, it was a celebration of apples, apple cider, apple pies — and a huge fundraiser for Staples organizations.

Betty Lou Cummings and a gift basket filled with (probably) apples.

The fieldhouse was filled with up to 10,000 visitors. Booths, games, food, fun — it was all there. Any high school club or team could offer anything.

One of the most popular, year after year, was Staples Players’ Haunted House. Coming right before Halloween — and with teenage actors eager to entertain (and scare) little kids, it was a no-brainer.

The cast of Staples Players’ Haunted House.

Eventually, CLASP joined as a sponsor, and recipient of funds.

With Election Day around the corner, the Apple Festival also attracted politicians. Bob Dole showed up one year, stumping for someone I’ve long since forgotten.

Today, the Apple Festival — like the Great Race and Festival Italiano — is just a memory.

We’ve got new traditions, like the Slice of Saugatuck.

How do you like them apples?

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7 responses to “Friday Flashback #322

  1. William M. Banks

    I was on the founding committee with Betty Lou. The first-year drawing prize was an Apple keyboard, which was a big deal back then.

  2. Jennie G Pickering

    the Apple Festival was the best!

  3. Westport once had a first selectman, Herb Baldwin, who owned an apple orchard. People would pick their own apples, paying by the bushel.

  4. Chip Stephens SHS 73

    Expired annual events: Don’t forget The Great Race of the 70s and the Christmas Walk of the 60.s

  5. The Apple Festival was one of our family’s favorites and one of Westport’s major annual events. It would be wonderful if it were revived.

    In addition to food and drink and various celebrations of the Fall, the Festival hosted many charitable and civic organizations which set up booths and distributed informational material. It created a terrific community weekend.

  6. Dorrie Barlow Thomas (SHS '86)

    I would love to know what year that Players Haunted House group photo is from. I swear that’s 1985’s group, but maybe these people are all doppelgängers. Anyone know for sure who some of these people are? I’m thinking I see Dave Kramer, Chris Hartel, Adam Marcus, and several others I recognize but can’t come up with their names. Any thoughts anyone?

  7. It was such a fun event. The dunk tank (with Mr. Yovan?) was a hit.