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I-490 New York
37.40 miles ; Interstate 490 serves Rochester, connecting at its east and west ends to I-90 (the NY State Thruway).
Near Rochester, I-490 was completed in three segments: 
An early component of Cleveland's expressway planning was the Innerbelt, part of a 1944 metropolitan plan including an outer beltway and seven radial freeways.  The Innerbelt, which now comprises portions of I-90 and I-71 , was completed in 1959.
In 1978, Interstate 490 was planned for 9.6 miles.  This would have been the Shaker freeway, running along the north end of affluent Shaker Heights. Writes Stephen Rojak: "What were they thinking?"
Possible I-490 extension was considered in early 2002
Many Cleveland freeways are more than 40 years old (and as the Innerbelt study emphasizes, each year includes a northeast Ohio winter), and will need rehabilitation or replacement by 2010. ODOT and a consulting team are taking the opportunity (from late 2001 to late 2003) to reassess traffic needs and come up with alternatives for improving the network. The University Circle Access (UCA) Freeway Concept is the most intriguing for road fans: extend I-490 east and north along railroad right-of-way to meet I-90 near 133rd Street. Interchanges could be provided at East 55th St, U.S. 422, Buckeye Rd/Woodland Ave, Stokes Blvd, Euclid Ave (near East 118th St), Superior Ave, St. Clair Ave, and I-90. There's a nice map of all this at http://www.innerbelt.org/Answerforalternatives/graphs/univ%20circle%20freeway.png. (Thanks to Marc Fannin for sending the link).
(Or, possible I-490 decommissioning)
Another alternative from the Innerbelt Study is just as drastic: downgrade existing I-90 north of I-77 to a boulevard. Build a new I-90 in the same path as the proposed I-490 extension above. The existing I-490 would become part of the new I-90, and I-490 would be no more.
... but it was judged far too expensive
In February 2002, the idea of building a new highway through the East Side, regardless of its route number, would "pose extraordinary environmental and capital costs."  There are several options still on the table, including a $476M reconstruction of the Innerbelt, but the new highway is dead. See also: