By Gretchen Webster

WESTPORT — Longtime Westport residents are all too familiar with chronic problems caused by a lack of parking downtown, where a succession of proposals to address the issue has faltered and stalled with little or no success.

At a recent Downtown Plan Implementation meeting, for example, someone in the audience called out that it’s been “30 years” since efforts to solve parking problems were launched, only to be contradicted by another person who said it’s been “50 years.”

Both were right.

In the 1950s, Evan Harding, a landscape architect and owner of the former Daybreak Nursery, designed the Parker Harding lot to include green space and riverside plantings, much as DPIC, 70 years later, wanted more riverside green areas in recent redesigns for the Parker Harding lot. 

The lot, named after Harding and Emerson Parker, a town selectman at the time, was designed to resolve the lack of downtown parking that even then had plagued the town for years.

Thirty years after Harding drew up plans for the parking lot, the parking crunch again was at the top of the municipal agenda in the early 1980s. 

Ronald Friedson, owner of the Tack Room on Post Road West, joined with the Westport Chamber of Commerce “to help come up with a solution to a problem that has plagued Westport merchants for the past decade — parking,” according to an article published in the Westport News in September 1980.

A  few months later, in an article headlined, “Parking frustrates police and merchants,” the president of the Downtown Merchants Association at the time, Daniel Coughlin, also sounded off on a continuing shortage of downtown parking. “For twenty years we have lived with this problem … no one wants to do anything,” he said.

Mini buses were pressed into service by the Westport Transit District in the 1970s in an attempt to lure drivers from their cars as a way to ease the parking crunch and traffic congestion. The effort even attracted attention of The New York Times, which headlined an article, “Westport Rediscovers the Bus,” in 1974.

By 1981, the transit district hired a consulting firm to conduct a $25,000 traffic study of the still-troublesome vehicular and pedestrian problems.

Although officials were hoping to address the issues by using the small buses to transport people from their cars to jobs and shops, it hadn’t been working. “So far, we haven’t been very successful in wooing shoppers to take the buses,” Martha Hauhuth, the first selectwoman at the time, said in a newspaper article. “It’s up to the merchants to decide what to do with Main Street,” she said.

The New York Times once more was prompted to cover Westport’s thorny downtown problems in an article headlined, “Customers and Complaints Mingle on Trendy Main Street,” in November 1990, and another, “Is Heart and Soul Gone From Main Street?” in December 1998.

One more radical idea — banning traffic on Main Street to transform it into a pedestrian shopping district — was even considered, but later rejected in the “Westport Center Plan” published by the town in 1987.

“There is a desire to officially drop the ‘closed-street mall’ concept on Main Street that was recommended in the 1975 Town Plan Update,” the 1987 Westport Center Plan read. “There is also a desire to officially drop the concept of constructing a parking structure or structures in the downtown area,” the plan also said. “A structure or structures would not enhance the desired aesthetic character of New England charm of Westport Center.”

And yet, the 2015 Master Plan for Downtown Westport resurrected the idea of evaluating the need to build “structured parking” at the Baldwin parking lot.

Today, many of the same options considered over the decades to help ease Westport’s parking issues are again under review, such as the possibility of building a downtown parking structure and providing public transit to shuttle downtown employees and shoppers to outlying parking lots.

Building a parking structure in downtown is an option that many have said is the only way to solve the chronic lack of downtown parking. And the concept is being studied again by DPIC, which earlier this month issued a “Request for Proposals” to update the 2015 parking study and analyze the feasibility for “structured parking” downtown.

And plans to remodel the Jesup Green area to accommodate more parking have also been considered many times before — years before the most recent plan to carve new spaces on the upper green was rejected by the Representative Town Meeting this May.

The 1987 Center Plan called for three major studies of the Jesup Green area to be “revised and coordinated” — the Jesup Green Study (1978), the Library Master Plan (1982) and the Police/EMS Building Renovation/Future Parking Plan — covering many of the same issues being studied again today.

Have any of the downtown projects proposed over the years, designed at least in part to solve the parking crunch, been accomplished? 

A few outlined in the 1987 Westport Center Plan actually became reality. 

The Westport Library’s move from Post Road East to the Jesup Green area is one such plan.

Another proposal that was realized called for building a road through the Parker Harding lot to connect Main Street to Post Road East. But that “cut-through” road was slated to be removed under controversial plans floated by DPIC last year to upgrade the lot. Amid furor over the plan, the road was restored in a revised proposal that officials called “a compromise” last August.

Now, rejection of plans to use Jesup Green for additional parking, coupled with a lawsuit filed in May challenging the Planning and Zoning Commission approval of the Parker Harding redesign, have left downtown planners searching for new routes — via another public-engagement effort — to address the familiar, decades-old problems.

The Board of Selectwomen is scheduled to vote on awarding a contract for that program at Wednesday’s meeting.

Freelance writer Gretchen Webster, a Fairfield County journalist for many years, was editor of the Fairfield Minuteman and has taught journalism at New York and Southern Connecticut State universities.