Past Projects

Since the first Small Business Challenge in 2017, small business owners, business associations, and groups of neighborhood businesses from across the city have used the program's grant funding to energize and invigorate their commercial areas and business districts through a variety of creative projects, design improvements, and branding/marketing advancements. 

2022 Small Business Challenge Winners

  • Cambridge Local First created a digital marketplace and hosted virtual walking tours to complement the digital holiday shopping guide which promotes their Cambridge business members.
  • The Harvard Square Business Association installed new Adirondack chairs for public use in common areas around Harvard Square.
  • Businesses located on the 2200 block of North Mass Ave (Spindler Confections, Curio Spice, Urban Hearth, and Nussli 118) installed a large group sign to attract new customers and help destination shoppers.
  • The businesses of Observatory Hill (at the intersection of Huron and Concord Ave.) hosted an expanded holiday shopping event that had branded swag and collective decorations.

2021 Small Business Challenge Winners

2020 Small Business Challenge Winners

2019 Small Business Challenge Winners

2018 Small Business Challenge Winners

2017 Small Business Challenge Winners

Read how the Small Business Challenge projects impacted small business owners and business districts

To learn more about eligibility and application guidelines, visit