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.

Randy Herbertson

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 Developed 7 years ago, it is now “a bit outdated,” Herbertson admits.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.

A slender ribbon of green separates the Saugatuck River from Parker Harding Plaza. (Photo/Amy Berkin)

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.

Among the new businesses downtown: Capuli restaurant.

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.”

Downtown Westport. (Photo/John Videler for VIdeler Photography)

13 responses to “Randy Herbertson Has Plans For The Downtown Plan

  1. A number of us already find Downtown to be “walkable.” And what we see when we walk is what you show in the picture of the slice of grass near Parker Harding: a whole bunch of garbage. We see it every time we walk by there. We make calls. Send e-mails. We talk to the surrounding businesses. We pick up some ourselves if we happen to remember to bring gloves and a bag. It never seems to get any better. I imagine a good amount of it blows into the river. I’m glad he mentioned “trash pick-up” as being on the list. But it shouldn’t be on a list of something we’re going to look at some months from now. WDMA or the Town needs to take responsibility “yesterday” for a regular (think “daily,” not a “once a season” community effort) coordinated cleaning these areas and better disposal practices to minimize the litter in the first place.

    • This is a big issue with chain stores vs. locally-owned. A local shopkeeper takes pride in the establishment and keeps it clean inside and out. A chain uses low-wage retail workers who punch in and punch out . Drive by the back of any of the chain store strip malls and you’ll see what I mean.

      The opening of the current Starbucks opposite Carvel was a great example. There was some snafu with their garbage service, and instead of using their own initiative to get it carted away, they let it build up until the mini dump dominated the already inadequate parking lot.

    • Given there a public spaces beyond which even dedicated shopkeepers would include within their cleanup territory, Westport merchants might consider the Business Improvement Districts as in NY commercial zones in which the landlords contribute to a fund hiring private sanitation people to sweep and pick up trash.

      • You hit the nail on the head, Peter. That corner pictured opposite Starbucks has a Dunkin cup and a Coke bottle, so Starbucks management may rightly say “wasn’t us.” Not to open another can of worms, but Compo stays generally clean because there is staff that cleans it every day. The rest of the town’s public spaces, especially where people tend to eat, needs the same. I imagine that some people might be less likely to litter if there wasn’t already litter underfoot.

  2. Sounds great! Parking lots here have the best views in Westport. Great idea to flip as many as possible! Good luck!

  3. To enhance downtown shopping and strolls consider two electric small town shuttle busses that run from all the parking lots down the retail and restaurant offerings throughout downtown. Free ridership and open easy to step off spaces and and quick on and off access. Growing and improving shopping for the merchants and restaurants will keep downtown a unique experience for townspeople and visitors alike!

    As a more radical and expensive idea to enhance the river and more open views take the parking lot between the river and main street shops and put in a two level underground parking and create an open park like setting at ground level with walks, sitting and open space for enhancing the river side.

  4. While parking and litter pickup are nice things, a bigger one in drawing people to downtown is having a place to buy frequently needed items like groceries, cheese, fruit, wine, etc.

    Decades ago downtown had all of these things, but they’ve progressively moved outward towards the Fairfield and Norwalk town lines.

    Re: groceries, I’m not saying there’s room for a full supermarket downtown, rather something equivalent to Gristedes or Westport Food Center for those who remember.

    But, it’s got to be more than just some artisanal butcher selling chicken for $19.95/lb.

  5. Don Willmott

    I always thought that making the Baldwin lot into a double-decker parking lot made sense because it slopes down so steeply. Done right, it wouldn’t be very obtrusive. Then…remove some of the riverside parking at Jesup and Parker Harding.

  6. Donald Bergmann

    The re make of Parker Harding to enhance the river location and related possibilities is the first of any major projects. Members of the BoF have spoken publicly in favor, as have most on the P&Z Commission, many on the RTM and of course our First Selectman. I believe each of the possible candidates for First and Second Selectman, the election is in November, also place Parker Harding as a priority. it will happen, the question is when.

    Now is the time to plan and once, next year, with the completion of the work on the Baldwin Lot, the time to implement will arrive. Whether the changes to Parker Harding tie into the long discussed dredging of the Saugatuck River, the creation of a pedestrian bridge from Gorhan Island to the other side of the river, even design changes that have Main Street stores look more towards our wonderful river, will be discussed and decided upon. Aesthetics will be crucial. A new Parker Harding will be an exciting development for Downtown Westport, Randy and many others will spearhead the effort and its gestation and birth can be a metaphor for our awakening from the pandemic. Our next First Selectperson will be a champion of the undertaking.
    Don Bergmann

  7. As a furthur idea for downtown, the full closure of Main street to Elm street and a conversion to a public promenade would be a wonderful addition to the downtown. This type of conversion has been very successful in a few small towns in the US like Boulder Colorado and Aspen, Colorado. You can visit these promenades with online images and see the asthetic. People stroll, shop, walk with their families, children, pets and enjoy good social interaction with neighbors and visitors alike.

    As for an underground parking at Parker Harding, no it won’t sink and alas with current construction and engineering it won’t flood or float either! Underground parking has been used in several cities in the US right up against full rivers, ocesn and bays with great long lasting sucess Let’s face the fact that above ground large parking lots of cars and trucks are butt ugly and the less we see them but have good parking available is a good thing for any local. Use the great backdrop and beauty of the Sauatuck river as a wonderful enhancement to downtown Westport, not as a parking lot feature!

    Westport needs to think out of the box with new vibrant ideas, planning and execution. Today there are better ways to use public space and activities.

  8. Annette Norton

    I want to respond to the above comment regarding closing Main Street. As a small business owner on Main Street I have a first hand perspective on this issue. I with Ray have also been to areas where they have closed the “Main Street” and enjoyed the experience. However, the places Ray is speaking of are tourist destinations. Westport downtown businesses rely on Westporters. The people that visit Westport are not enough to support the businesses downtown. The numbers do not lie. I can speak from my own experience and on the days that Main Street has been closed for events (other than Sidewalk Sale) have had a more than 50% loss in revenue consistently. I have heard many concerns about parking. People do look to park on Main Street and use it to more easily navigate to other parking areas. People are dissuaded to shop Downtown when they perceive there is not easy access with their vehicle. My comment is made because I love downtown and Westport and truly care about our Downtown.