Creativity Connects Westport: Meet Tom Fiffer

Creativity Connects Westport

What fuels a vibrant, connected and creative community? What makes people feel good about living in Westport?

When locals share the creativity that they uncover in the nooks and crannies of their community it brings about connectivity and makes us all feel good. Believe it or not, you discover creativity every day as you walk, shop, work, and play in Westport? 

Meet Westport resident Tom Fiffer, writer, author, storyteller and founder of Christmas Lake Creative.

How does creativity connect you to Westport?

To outsiders, Westport, Connecticut, looks like any other wealthy coastal suburb, with its mix of gracious homes and modern mansions, upscale restaurants and pizza joints, top-ranked schools, and, of course, beautiful beaches. But the town has a long history as a home for creativity, before we had MoCA Westport, the Playhouse, and a library with a maker space—to name a few of the institutions that make me feel good about living here.

In the Roaring 20s, F. Scott Fitzgerald and his wife Zelda spent a summer near Compo Beach, and some believe Westport was Fitzgerald’s inspiration for West Egg in The Great Gatsby. During the booming post-war 50s and 60s, Westport was home to authors such as Max Shulman (who immortalized the town in Rally Round the Flag, Boys) and Robert Ludlum, illustrators (Hardie Gramatky, creator of Little Toot), television writers (Rod Serling, The Twilight Zone), scores of “Mad Men” types, and of course, Paul Newman and Joanne Woodward. There was even the Famous Artists School, founded in part by Norman Rockwell.

Creativity is in the air here, and I am constantly inspired both by the natural beauty of the town and the contributions of its famous residents. I no doubt visit the same places they did to light their creative fires or find the quiet all creatives need to clear our heads for the next endeavor: Compo Beach, with its painterly sky and glorious sunsets; the little wooden walkway over the Saugatuck off Parker Harding Drive; the green stretches of Winslow Park for contemplative walking; the winding streets of the Old Hill neighborhood for a trip through colonial history; or Sherwood Island State Park to commune with the geese and, on a clear day, catch a glimpse of Manhattan. When I go out in Westport with my mind opened to creative possibilities, I am never disappointed.

For the first ten years, I was really only here on weekends, as I commuted to New York for a job in business information. Frustrated with endless hours on the train, I began writing a blog, Tom Aplomb, during my morning ride. The daily discipline of penning (actually tapping out) posts helped me become an editor at an online magazine, The Good Men Project, and for a short time, I helmed Westport’s HamletHub. My day job ended in 2014, and as I began to move in more creative circles, I started teaching at the Westport Writers’ Workshop.

Eventually, I opened up my own workshop with my writing partner, Julia Bobkoff. We named it Christmas Lake Creative, after the street, Christmas Lake Lane, where our home and business are located. We offer group classes in creative writing, fiction, memoir, screenwriting, and a course for young writers (13-18). We also work one-on-one with numerous writers, helping our clients develop their memoirs, novels, and projects for television and film. During the pandemic, we’ve been offering a free Zoom creative writing class on Thursday nights to keep people’s creative juices flowing. Whether people know Westport’s history or not, they all seem drawn to this remarkable town’s creative energy, and we love living and working in such a storied setting.

Thomas G. Fiffer is a writer, editor, founder of Christmas Lake Creative, and author of two books—Why It Can’t Work: Detaching From Dysfunctional Relationships to Make Room for True Love, and What Is Love: A Guide for the Perplexed to Matters of the Heart.

Creativity Connects Westport made possible by LIFEWTR.

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The views and opinions expressed above are those of the author and do not necessarily reflect the views of HamletHub or LIFEWTR. 



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