VT 289 opened to traffic in October 1993 and comprises part of the Chittenden County Circumferential Highway, a proposed partial beltway around the northern and eastern suburbs of Burlington.

East of VT 15, the highway veers eastward to meet Essex Way, then gradually turns to the south toward the Winooski River as it traverses several small hills.

[3] Midway between Essex Way and the riverbank, several unused ramps intended for an interchange with Allen Martin Parkway extend outward from VT 289.

[1][3] The highway continues south to the Winooski River, where it terminates at a partial interchange with VT 117 east of Essex Junction.

[5] One of the main concerns that this road was to alleviate was the traffic congestion plaguing a five-way intersection in the center of Essex Junction.

[8] I-289 was effectively redesignated VT 289 when the Vermont General Assembly added the road to the state highway system that same year.

[2] In May 2011, Vermont Governor Peter Shumlin announced that the Circumferential Highway, as originally conceived, would not be built,[10] although the full right-of-way for the road had already been purchased.

On November 19, 2004, the United States Department of Transportation filed a notice of intent to complete an Environmental Impact Statement (EIS) on segments A and B of the proposed route; that is, the section between Interstate 89 in Williston and the current eastern terminus at VT 117 in Essex.

The first forum discussed VT 2A, which has become an arterial road due to substantial development in the late 1990s and early 2000s around I-89's exit 12 in Williston.