Great Scott! Annual Gatsby Day Is Proposed

On May 14, 1920, F. Scott and Zelda Fitzgerald signed a lease to rent 244 Compo Road South.

Deej Webb — whose film and book about the famous couple’s wild time in Westport has shined a light on both their literary legacy, and our town’s Jazz Age days (naked swims at Compo Beach!) — wants to make May 14 an annual holiday.

It would be called “Great Gatsby Day.”

F. Scott and Zelda Fitzgerald, Photoshopped in front of their Westport home.

The 1980 Staples High School graduate/history teacher/amateur historian is circulating a petition. Citing Westport’s influence on “The Great Gatsby” (and other Fitzgerald novels), it says:

We want to insure that the town celebrates and treasures its connection with the Fitzgeralds and the book.

Furthermore, in times of rapid change we wish to ensure that this town’s marvelous history is not lost.

Webb envisions events at the Westport Historical Society and Westport Library; a tie-in with the Longshore flapper party; a walking tour of Longshore-influenced scenes from “Gatsby” and “The Beautiful and the Damned,” and more.

He’s open to other ideas from the community too.

Maybe another naked swim at Compo?

(To view — and sign — the petition to make May 14 “Great Gatsby Day in Westport,” click here.)

8 responses to “Great Scott! Annual Gatsby Day Is Proposed

  1. Bill Boyd (Staples '66)

    I really like this idea to preserve the connection!

  2. What a a great idea! But I think the event needs to have a game of croquet at the Longshore Club to give it that 1920s feel that Fitzgerald experienced as the occupant of the house near the Longshore property.

  3. My copy of Boats against the Current arrived this week & is a belated 92nd Birthday gift to my mom Sally Deegan who recalls the gossip of the time…her 1st date with my dad, Don Kellogg, was to The Compo Inn.

  4. Bonnie Bradley

    Go for it, Deej!

  5. Jack Backiel

    I want to lose 15 pounds this year. I only have 18 more to go! Once I reach my goal, I’ll participate in a 06880 skinny dipping party.

  6. Arline Gertzoff

    Key West has a Hemingway Festival so why not an F Scot and Zelda Day Have a Reading by a Fitzgerald scholar and a frivolous event or two Next aJD Salinger Fete ,etc A better idea would be an author festival for all the luminarie writers who made Westport home at one time or another

  7. Dave Lowrie

    Go Deej! Fab idea Old Sport!

  8. WHS has an exciting walking tour scheduled for July 28 at 3pm, Destination Westport: In Gatsby’s Shoes, with Deej as our guide! Go to to reserve