In 1956, the Westchester County Planning Department proposed an expressway connecting the eastern part of the county with Stamford, Connecticut. The proposed route would have permitted traffic entering Westchester from southwestern Fairfield County and destined for northerly points to connect with the various north-south arteries. The proposed expressway route was recommended again throughout the 1960's by various planning agencies.
The proposed Pound Ridge-Stamford Expressway was to utilize the alignment of NY 137 and CT 137 throughout its entire 12-mile length. It was to begin at the proposed Ossining-South Salem Expressway (NY 172) just north of Pound Ridge, continuing south between the existing NY 137 (High Ridge Road) and the Mill River into Connecticut. Interchanges were to be provided at NY 124 (Westchester Avenue), CT 15 (Merritt Parkway), CT 104 (Long Ridge Road), US 1 (Boston Post Road) and I-95 (Connecticut Turnpike). In the city of Stamford, the proposed CT 137 expressway was to have been included as part of a downtown urban renewal project.
A decade later, the Westchester County Planning Department, the Connecticut Highway Department and the Tri-State Transportation Commission recommended construction of the Pound Ridge-Stamford (Route 137) Expressway from I-95 in Stamford north to NY 35 in South Salem. The expressway between I-95 and CT 15 was designated as a "priority segment" for completion by 1975. North of CT 15, the expressway was designated as a "long-range" proposal for completion by 1985.
The Commission stated the purpose and benefits of the NY 137-CT 137 Expressway as follows:
By filling a gap in the regional highway grid, this north-south expressway will relieve congested arterials and distribute traffic for radial routes. It will serve to tie the suburbs to a redeveloped city center.
Because of funding difficulties and intense community opposition, the Tri-State Regional Planning Commission, the successor organization to the Tri-State Transportation Commission, dropped the Pound Ridge-Stamford Expressway from its list of recommended projects in 1975.