Cobblestone streets in Peekskill will guide walkers to the heart of the city. Old buildings, iron street lamps, and a scent of history and memories will be part of the tour promoted by the Peekskill Business Improvement District (BID) on Saturday, October 4. The event, beginning at 10 a.m., will explore the historic architecture of Peekskill’s northern sector and its hidden treasures.
The tour will depart from the Hudson Valley Gateway Chamber of Commerce, located at 1 South Division Street. From there, visitors will walk through the historic corners of the city. The activity, aimed at the general public and free of charge, will be led by David Kaminsky, a member of the BID board, who has promoted these tours since 2023 to connect the neighborhood with its own heritage. According to official figures, in its first year, the tours attracted an average of 15 participants per event, with attendance on the rise.
Kaminsky noted that nearly every building in downtown Peekskill carries historical significance, yet the initiative has been structured around two distinct tours encompassing 26 notable sites.
“The goal is two-fold: Share Peekskill’s history with residents and visitors alike, and while walking through the downtown, we point out places to shop and dine,” he explained.
On Saturday, the group will follow the northern route, which includes North Division Street and Main Street. Kaminsky stated, “There are 12 locations we highlight along the way, ranging from the site of Harriet and Hawley Green’s barber shop to St. Peter’s Church, to Monument Park, to City Hall and the former Evening Star Building.”
The Chamber of Commerce functions as the gateway to the north route, which traverses a series of streets lined with buildings of different periods and styles, some of which bear witness to Peekskill’s industrial boom during the second half of the 19th century, when the city consolidated as a Hudson Riverport and a railroad hub.
During that period, machinery factories, mills, and metal workshops flourished. These industries drove the construction of most commercial and residential buildings that today form the historic downtown.
On that point, Kaminsky emphasized a detail that often goes unnoticed: “We always tell guests, ‘Look up, look up!’ We have amazing architecture at the tops of many buildings, some with names of the original owners and the date the building was constructed.”
Kaminsky has served as the voice and guide of these walks since their inception. His role is not that of a lecturer but that of a conductor accompanying the group on foot, marking stops in front of exteriors that summarize the city’s urban evolution. In this case, the route heads north, an area with examples of residential and commercial buildings that have withstood the test of time. Although the objective may seem simple —showing the city’s architecture— the BID’s motivation is deeper: to trace a continuum between past and present that strengthens Peekskill residents’ sense of belonging.
During walks, residents often ask about new businesses, Downtown Revitalization Initiative (DRI) projects, or upcoming shows at the theater.
“We like spontaneity,” Kaminsky added. “We often take advantage and stop in the Paramount so people can see the amazing interior, a local business like the Bean Runner (where the owner often comes out and gives more of the history of that building), or an artist loft like in The Old Field Library building.”
The tours also serve as a tool to attract foot traffic downtown. Frequently, the guide hears participants remark, “I did not know that was here,” or, “I was always thinking about eating there. I will have to try it.” At times, some even “decide to extend their visit and shop at the Flat Iron Gallery, dine at Whiskey River or Ruben’s, or pick up fresh produce at the Farmers Market.”
For those unable to attend the guided tours, Peekskill BID also provides self-guided maps, available at the Chamber of Commerce and other locations throughout the city. The brochures include a detailed route and historical information. According to Kaminsky, “We are planning to coordinate with the Peekskill Museum to be open when we do tours, so folks can see the exhibits. That’s planned in conjunction with the celebration of the 250th Anniversary of the American Revolution.”
To participate in this community activity, prior registration is required by emailing [email protected]. Additionally, organizers recommend participants wear comfortable shoes for the 90-minute walk, bring water for the route, and, in case of rain, be alert to possible rescheduling.
