The Hillsdale Community Foundation was founded in 2008 by a group of people interested in creating a non-profit that would allow community funds to go directly into neighborhood improvement. Their annual fundraiser, the Hillsdale Book Sale (most recently expanded to be the Hillsdale Book & Art Sale) raised funds each year for the effort. In 2009, the Hillsdale Community Foundation Board of Directors decided to implement their first project. The started by holding a community meeting, offering $3,000 for a community project, and asking participants what they would prefer to spend the funds on. The result was more bike racks, specifically in an area on the South side of the district between Food Front and Baker & Spice Bakery. A group of volunteers, now called the Bike Coalition, formed to move the project forward, leveraging the funds to obtain even more, resulting in early 2011 in what is now called the Bike Plaza.

Meanwhile, in 2010, the City of Portland created the Portland Main Street Program, a neighborhood commercial district program based on the very successful Main Street Approach® used in towns and cities across America to revitalize older, traditional business districts. Portland Main Street followed the lead of urban main street programs in Boston, Chicago, Baltimore and Washington DC, while adding its own unique approach and emphasis on sustainability. After a competitive application process, Hillsdale Main Street, along with Alberta Main Street and St. Johns Main Street, were born.

After four years of grant funding from the city came to an end, the organization transitioned away from the Main Street Program, and back to its roots as the Hillsdale Community Foundation.