The earliest additions of fill to Riverside Avenue likely occurred between 1930 and 1932. Newspaper articles describe construction on Riverside Avenue to add a sidewalk and widen the roadway in 1932, using the additional surface area provided by fill placed the prior year. In 1955, a series of landslides through the late summer and fall wash out Riverside Ave multiple times. City officials alleged that water from a disused culvert had eroded the road foundation. The damage was severe enough that the road was bypassed by vehicles until it could be rebuilt. In the decades that followed, old cars, construction waste and various other debris was dumped down the slope. Several smaller slides occurred throughout this time period, especially following large storm events. By the 1970s, the slope was filled to be level with the roadway.
Heavy rains caused a major landslide in 1976, which dumped large amounts of debris into the Winooski River. In 1981, a major landslide caused by illegal dumping led to criminal charges for a property owner. By 1983, the city of Burlington was looking for a method to starch Riverside Ave as a stop-gap solution to the rapidly destabilizing slope. Clay was removed and the slope was filled with sand and stone to provide better drainage. In 2019, a major storm on Halloween caused a landslide on Riverside Ave just above the Riverwalk.
The changes in Riverside Ave are evident when comparing aerial photography of Riverside Avenue from 1937 and a 2018 orthophoto.