Past the church it turns north again to include all the buildings of Ossining High School while excluding its more modern athletic facilities.

Industries that had been a source of Ossining's early growth, such as boat-building on the riverside and transportation-related businesses like hotels along Albany Post Road, suffered.

While shipbuilding and river shipping finally faded as an industry when the railroad, now part of the New York Central, was fully established, quarrying continued.

The village had become an industrial center, with over a hundred small businesses located downtown or on the waterfront, from Brandreth's pill factory to pickle and sleigh manufacturers.

On the other side, 61 Central retained its cast iron storefront with columns on high plinth blocks, the only example of that design element in the district.

Trinity has elements in common with the other churches in the series, such as its mix of materials and large rose window, but is unique among them for its U shape, the result of a later expansion.

[1]: 26 At the beginning of the next decade, another longstanding building from the early years of Ossining, the Union Hotel at South Highland and Church Street, was demolished.

[10]: 218  In 1892 the corner section of the Barlow Block was separated internally from the rest of the building so it could serve as Ossining's post office, the first of two former locations for that facility within the district.

It was refaced in stone, with Doric and Ionic pilasters, terra cotta detailing and full entablature leading up to a tile roof,[1] meant to emulate St. Mark's Library in Venice.

The stone building by Lansing C. Holden, a past president of the New York chapter of the American Institute of Architects, is the only example in the village of the Beaux-Arts style.

The stone edifice at 16–20 Croton Avenue, the northern end of the district, was in the Classical Revival mode common for most governmental buildings of the era.

It is the only Westchester building by Donn Barber, designer of the Connecticut State Library and the first American admitted to the French Society of Beaux-Arts architects.

After several attempts, voters in 1929 approved a new building when a nearby private school made a donation that helped cover the $750,000 ($10.9 million in 2023[12]) construction cost.

The Collegiate Gothic building, taking up the large area of South Highland's west side between the houses and the Methodist church, has some similarities to Harkness Tower at Yale University, also designed by Rogers and considered one of the best examples of that style.

The village used its urban renewal grants to demolish the old buildings along the south side of Main Street that year in an attempt to revitalize downtown.

In 1975, the village followed up with a study of the prospects for rehabilitating and preserving downtown that, for the first time in its planning history, drew on community input.

A second plan two years later also failed, but made specific recommendations for preserving historic buildings and called for new development to be on the same scale, rather than the larger structures proposed at the beginning of the decade.

[1]: 12  Many businesses that closed or moved out were replaced by new ones, particularly restaurants, that catered to a growing Latin immigrant (at the time, largely Ecuadorean) population that had settled in the neighborhoods nearby.

[21] Extensive public involvement led to the implementation of ideas from earlier plans, such as design guidelines for the district and a Historic Review Commission to enforce them.

[17]: 24–25  In 1992, the aqueduct gained National Historic Landmark status,[22] and the following year the 1840s Greek Revival buildings at 147–55 Main Street burned, creating a new void for redevelopment; the village initially used the space as a parking lot.

The post office moved out of its building for a newer facility on the south side of Main Street, in the space cleared three decades earlier by urban renewal opposite the western extent of the district.

[8]: 41–54 To the first end, it recommends making the village's government more user-friendly for existing and prospective businesses, addressing the 18 percent vacancy rate reported in 2007.

[8]: 44–47 During the process of drafting the plan, many residents expressed a desire for a national chain retailer or restaurant to be enticed to locate near or in downtown as a draw.

Chains do not like to pioneer a new area, instead preferring to cluster with each other, and this leads to the development of large strip malls, impractical and undesirable in downtown Ossining, which still shows the scars of previous demolitions for urban renewal.

Ossining as a whole is also geographically undesirable for chains, since not only is it neither affluent enough or accessible enough from major highways, the Hudson River cuts the potential trade area for such stores in half.

The plan also recommends both improving cultural offerings downtown, and promoting more residential and office use to increase foot traffic at more times of the day.

The plan recommends creating a village green on part of the lot at the southwest corner of Main and Spring streets, outside the district, as a focal point of downtown.

[8]: 51–60 The plan also recommended improving connections between downtown and the waterfront, where the Metro-North commuter rail station or the Haverstraw–Ossining Ferry could bring visitors into the village without adding to the parking problem.

[8]: 53  The plan further suggests studying the possibility of establishing a jitney or shuttle bus service that would not only allow visitors to bypass the steep climb up Main Street from the waterfront to downtown but continue westward to the residential areas of the village and town.

In July, a steering committee, with mayor Victoria Gearity, village trustee Quantel Bazemore, planning board member Jeff Gasbarro and six citizens, was appointed.