In 2014 WINGS launched a $10,000 Dare to Dream grant to be awarded to an area non-profit which WINGS felt had the most compelling dream to help women and children in the Northfield area reach their full potential. WINGS sought proposals that were innovative, impacted the community and built capacity. Applicants outlined ideas that could not be carried out without this financial award. This award did not take the place of annual grants, but rather created a new and exciting way to encourage applicants to take risks and dream big with either a new endeavor or an enhancement to a current initiative. This grant was offered again in 2016. Awards are as follows:
- 2014 - Dare to Dream was awarded to Northfield Healthy Community Initiative on behalf of the Community School Advisory Council to support Greenvale School as it became a community school, a place where children and families are supported through after-school care, community activities and clubs and other programs that build community around the school.
- 2016 - Dare to Dream was awarded to Growing Up Healthy to collaborate with ECFE and Northfield Promise to create a Latino Childcare Providers Network.