Last month, Randy Herbertson chaired his last meeting of the Westport Downtown Association. After 6 years he moves into the same role for the Downtown Plan Implementation Committee, an official town body.
Among the key activities of the DMA — whose mission is to “enhance the downtown experience for shoppers, diners and other visitors, with the goal of building business and economic vitality for our community” — Herbertson cites:
Trash collection and general outdoor maintenance not covered by local government. The town paid for the reconfiguration of Parker Harding Plaza, including installation of compactors with recycling. The DMA took over weeding and bed maintenance, with reimbursement from the town. Coming in 2022: “Baldwin and Church Lane.”
Beautification activation, including season outdoor décor. This includes a revitalized and upgraded banner program with non-profit partners; upgraded summer planting, including baskets, planters and barrels; street string lighting throughout downtown, and new holiday decorations, with street posts, barrels and a tree tour.

Main Street planters
Communication and collaboration with merchants and residents. Progress includes a website with robust merchant listings, commerce and event features; 250% membership growth, with bi-weekly digital and physical communication merchant support advertising and social media; consistent consumer communication via a database of 16,000, and exponential social media growth; long-term in-kind and paid media partnerships and relationships.
Sponsorship and oversight of events that reflect the varied interests of consumes, complements the district profile, and drives consumer traffic. The WDA revamped their event calendar to discontinue events that were not traffic drivers or financially manageable; added new events like Westoberfest, Fashionably Westport, and Health & Fitness Day; revitalized the Westport Fine Arts Festival by returning it to Main Street and beyond; enhanced Sidewalk Sales with street closures, additional dates and more support; closed Church Lane and added entertainment, and grew sponsorship revenue by 200%.
Collaboration with other Westport organizations having interests and responsibilities for downtown. This includes the Westport Weston Chamber of Commerce, non-profits, local and state governments such as the Board of Selectwomen, Planning & Zoning, Police and Fire Departments, and Westport Weston Health District.

The Fine Arts Festival returned to Main Street and environs.
Herbertson also cites partnerships with town and key constituencies “through the darkest days of the pandemic,” and the establishment of the WDA as a full non-profit 501(c)3.
He notes progress in areas like burying cables throughout the district; rebuilding Elm Street and Church Lane; the new Sigrid Schultz parking lot, and 2 upcoming projects: rebuilding the Baldwin lot (this spring) and revamping Main Street (this summer).
Starting in 2023, Herbertson says, “even more dramatic updates” will begin. A new design and build RFP will go out soon to address Parker Harding, Jesup Green and the Imperial Avenue parking lot.


Our community is deeply indebted to Randy for the guidance and hard work that he has committed to making the downtown area more appealing, more workable, and more accommodating for shoppers and businesses alike. It has been a great pleasure serving on the Committee with him.