Randy Herbertson Has Plans For The Downtown Plan

Better parking. Enhanced river access. Tech upgrades, including vibrant WiFi.

Those are some of the initiatives planned for downtown.

Now all Randy Herbertson has to do is implement them.

He’s not alone, of course. The revitalization of Main Street, Jesup Green and environs is a huge task, with public and private partnerships and investments.

But as the new chair of the Downtown Plan Implementation Committee, it’s Herbertson’s job to see it all through.

He’s hardly parachuting in. He and his wife Deborah have been here since 1998. But although they chose this town in part for its cultural offerings, for more than their first decade Herbertson was “that guy who saw Westport only in the dark.”

He owned a marketing and design firm in New York. She commuted too. It was only after he sold his business and opened The Visual Brand on Church Lane — and Deborah became creative director at Terrain — that he got involved in local affairs.

He went big. David Waldman encouraged him to join the Westport Downtown Merchants Association. He sat on the town website steering committee and the Westport Library board.

And Herbertson joined the Downtown Plan Implementation Committee.

The “plan” is the town’s Master Plan. Developed 7 years ago, it is now “a bit outdated,” Herbertson admits. But it’s a start.

The new chair hopes to prioritize the plan’s 4 or 5 major initiatives, by cost and complexity.

One key issue: Reimagining parking. First up, Herbertson says, is the Baldwin lot off Elm Street. That’s the easiest

Parker Harding Plaza is more complex. It involves rethinking green space, and the lot’s relationship to the Saugatuck River.

Jesup Green is the most complex. The ultimate vision, Herbertson says, is to flip the current parking with the adjacent green space. That would emphasize and maximize river access, while adding perhaps a playground or skating rink.

The greening of downtown, including technology upgrades, could solarize much of the area. A stronger WiFI network would enhance music capabilities.

Herbertson’s committee will also figure out how to create “more stop-and-pause places. People want room to move freely outside, then stop and dwell.”

The DPIC head points to the COVID-induced closing of Church Lane as successful. It led to increased dining and shopping, Herbertson says. Now he wants to build on that success.

Another issue: the best way to manage services like trash pickup and recycling.

“A good downtown is the heart and soul of a community,” Herbertson says. “It’s great to see that ours is becoming that again.” New businesses — restaurants, book stores and more — are opening up. Some are start-ups; others have relocated from elsewhere in town.

During his time as president, the Westport Downtown Merchants Association reinvigorated the Fine Arts Festival. They added special events for different populations — a fashion show, beer fest and more — and advocated for enhanced public/private partnerships. Cables were buried; sidewalks and curbs added.

Herbertson calls his roles with the Downtown Plan Implementation Committee and Downtown Merchants Association “synergistic.” The DPIC is an advisory body, he notes; the town controls all rules and regulations.

But, he notes, “everything the DPIC touches is something the WDMA is involved in.”

He also sees synergy with other initiatives in town — for example, the revitalization of Saugatuck.

“COVID taught us the importance of the retail community, as part of our town as a whole,” he says. “Whatever happens in one place affects the rest.”

So what does Herbertson’s idea downtown look like?

“Highly walkable,” he says.”Real strong integration of natural resources, especially the waterfront. Every space filled with a selection of things that are unique an good for the town, where people can stop and pause.

“And something for all ages.”