Denny Way begins as an offshoot of Western Avenue, two blocks uphill from Myrtle Edwards Park on the Elliott Bay waterfront and near the former Seattle Post-Intelligencer offices.

At 5th Avenue, adjacent to Tilikum Place and the KOMO-TV headquarters at KOMO Plaza, Denny Way passes under the Seattle Center Monorail and enters the South Lake Union neighborhood.

[1] From Westlake, Denny Way climbs a steep grade towards the Cascade neighborhood and passes the headquarters of The Seattle Times, which features a mounted news ticker.

[4] After an intersection with the diagonal-running Olive Way, Denny Way narrows into a two-lane residential street and shifts slightly north while passing several mid-rise apartment buildings.

[13]: 7  Denny initially named the road "Depot Street", as part of an unsuccessful attempt to build a major train terminal at its western end.

[14] The city government completed construction of a sewage tunnel under Depot Street in 1894, serving as the main outflow for northern Seattle.

[19][20] A section of Denny Way between Broadway and Nagle Place was closed for the construction of the Capitol Hill light rail station and was redeveloped into a woonerf.

[30] In the 2010s, transit advocates also suggested that Denny Way could be served by an aerial tramway system, with stops between the Olympic Sculpture Park and Capitol Hill station.