The village's 2009 comprehensive plan identifies three objectives for downtown: to promote it as a business location, create a major downtown draw for visitors and residents, and improve and enhance its amenities.
It recommends specific actions to accomplish all three.

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.
The Village Board and Planning Board should both be able to provide more information and reach out to local and regional business organizations.
The zoning process, the plan contends, could be improved, since many existing businesses downtown are on conditional uses, and site plan approvals should have a time limit, forcing owners to begin development.
Creation of a business improvement district and appointment of a Main Street Manager would make the development of downtown businesses more effective and efficient.

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.
The plan considers this ill-advised and unlikely to happen for several reasons.
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.

Instead, it recommends building on the existing clusters of restaurants and home-furnishings stores.
Two businesses in each, Doca's Portuguese restaurant and Melita's respectively, draw customers from all over the county.
Other regional chainlets could be drawn to Ossining.
Restaurants in particular could see more ethnic diversity, widening the existing focus on Latin fare.
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.

Residents also complained that the parking lots opposite the Crescent were unsightly, and that they found it difficult to find parking downtown.
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.
It could retain parking along the sides or even in a garage underneath, a common practice in Europe.
Further parking could be added in an aboveground garage on Brandreth Street, outside of downtown.
The village should also act to create a consistent downtown environment by encouraging infill development, making signage and lighting consistent, and strengthening and consistently enforcing its historic preservation guidelines.

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. "
A synergy between waterfront uses and downtown will enhance both areas, and provide reasons for visitors to stay in Ossining longer", it says.
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.
Other measures to enhance the connection include signage, improved walkways and lighting, and dedicated space for river views.

In 2019, the village began the process of updating the plan.
In July, a steering committee, with mayor Victoria Gearity, village trustee Quantel Bazemore, planning board member Jeff Gasbarro and six citizens, was appointed.
Several months later the village put out a request for proposal to identify a pla
The village's 2009 comprehensive plan identifies three objectives for downtown: to promote it as a business location, create a major downtown draw for visitors and residents, and improve and enhance its amenities. It recommends specific actions to accomplish all three.
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. The Village Board and Planning Board should both be able to provide more information and reach out to local and regional business organizations. The zoning process, the plan contends, could be improved, since many existing businesses downtown are on conditional uses, and site plan approvals should have a time limit, forcing owners to begin development. Creation of a business improvement district and appointment of a Main Street Manager would make the development of downtown businesses more effective and efficient.
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. The plan considers this ill-advised and unlikely to happen for several reasons. 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.
Instead, it recommends building on the existing clusters of restaurants and home-furnishings stores. Two businesses in each, Doca's Portuguese restaurant and Melita's respectively, draw customers from all over the county. Other regional chainlets could be drawn to Ossining. Restaurants in particular could see more ethnic diversity, widening the existing focus on Latin fare. 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.
Residents also complained that the parking lots opposite the Crescent were unsightly, and that they found it difficult to find parking downtown. 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. It could retain parking along the sides or even in a garage underneath, a common practice in Europe. Further parking could be added in an aboveground garage on Brandreth Street, outside of downtown. The village should also act to create a consistent downtown environment by encouraging infill development, making signage and lighting consistent, and strengthening and consistently enforcing its historic preservation guidelines.
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. "A synergy between waterfront uses and downtown will enhance both areas, and provide reasons for visitors to stay in Ossining longer", it says. 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. Other measures to enhance the connection include signage, improved walkways and lighting, and dedicated space for river views.
In 2019, the village began the process of updating the plan. In July, a steering committee, with mayor Victoria Gearity, village trustee Quantel Bazemore, planning board member Jeff Gasbarro and six citizens, was appointed. Several months later the village put out a request for proposal to identify a pla
Downtown Ossining Historic District