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This multi-state route was created in Connecticut as a north-south route, but now extends much longer inside the Empire State going east and west. In the 1960s, Route 35 was one of a long list of highways considered for a regional freeway network.
Just over the state line, NY 35 intersects NY 123; if you follow that road, you will eventually cross back into Connecticut on CT 123.
In the 1920s, Route 35 was part of New England route NE-3, a progenitor to today's US 6.
The modern Route 35, commissioned in 1932, has changed slightly in the intervening years. An old rotary at US 7 no longer exists; and the spot where it crosses the New York state line has changed twice.
In 1932, Route 35 followed West Lane all the way from Main Street in Ridgefield to the New York state line. (New York would not designate a continuation of Route 35 until about 1942). A year or two later, Route 35 was moved to South Salem Road, and the remainder portion of West Lane became Route 35A. In 1963, Route 35A became SR 835, which exists today. New York never designated a Route 35A on its side.
In 1940, Route 35 was moved slightly southward near the state line; Old South Salem Road is the older alignment. The new road had been designated SR 434 in 1939.
The late 1930s Route 35 (West Lane, South Salem Road and Old South Salem Road) was known as Bedford Road in the 1700s; if you followed that road into New York State (where it changes name to Old Post Road), you would move west then south to Bedford, N. Y. However, Route 35 takes a more westerly route to Yorktown.
This Post Road continued from New York State into Ridgefield along today's Route 35, then continued north into Danbury, where an old "Boston Post Road" east of US 7 marks part of the old route. This branch is not one of the three primary routes of the Boston Post Road from New York City to Boston. When the Danbury and Ridgefield Turnpike was laid out in 1801, postal traffic moved to that route.
Grander plans were in the wings for Route 35 a few decades ago. A 1956 New York plan called for a Route 35 freeway from Peekskill to Ridgefield, following CT 102 to meet the proposed US 7 freeway.
In 1966, the Tri-State Transportation Commission proposed an expansion of the freeway to New Haven via Monroe, Derby, and the Route 34 alignment. So would it be called 35, or 34? The TSTC instead called it the "Conn. 110 Expressway," citing its benefits as:
East-west route through the former Fairfield County. Fills 18-mile gap in regional highway grid. Connects rapidly developing suburbs. Extends stub-end expressway.
A few comments: "former Fairfield County" alludes to Connecticut's dissolution of county governments in 1960 (no, Westport did not slide into the sea). The "stub-end expressway" was the Oak Street Connector part of Route 34 in New Haven, which has mostly been removed. Route 110 does have an east-west portion in the corridor between Monroe and Derby, and is closest to the proposed alignment in that area. And finally, the TSTC was at the time quite interested in completing highway grids, filling gaps, and other geometric temptations. This made for some interesting ideas that had little chance of realization. (Also, note that the earlier TSTC has no relation to the modern-day Tri-State Transportation Campaign (http://www.tstc.org), which espouses a more environmentally friendly, less highway-centric approach to transportation planning.)
In 1969, the new Conn. 110 Expressway proposal surfaced in a dispute about a planned interchange at Florida Hill Road and the proposed US 7 freeway in Ridgefield. Residents nearly unanimously opposed the interchange at a town meeting, saying that 1) there were already two nearby interchanges proposed, at Route 102 and old US 7; and 2) this interchange looked like it was really in preparation for the Conn. 110 Expressway.
A DOT engineer replied that the Route 110 proposal was only "a line on a map", and that the state had no inclination to proceed with it – especially if residents did not want it. Furthermore, the Florida Hill Road interchange would be too small for crossing freeways; and the study line had Route 110 crossing US 7 to the south, at Route 102.
In 1975, the Regional Plan Association urged Connecticut not to proceed with its part of the plan. I haven't seen mention of reviving it since then.
In June 1973, DOT officials told Ridgefield officials that "there no longer exists any plan to extend Route 35 through Ridgefield or to expand Route 116." I don't have details of these plans, though.
Traffic is growing on the Route 35 corridor, but plans to address this do not include the freeway proposal from the 1960s. In 2003, the town of Ridgefield studied Route 35 traffic and figuring out ways to ease congestion. Problems include: lots of on-street parking and delivery trucks stopped in traffic lanes; and people using Route 35 and Route 33 as a "Route 7A" alternative to clogged US 7.
Improvements could include widening Route 35 or building a roundabout at its intersection with Route 33. The study was completed around 2004.