Ross Benincasa is a community development leader and strategist with more than a decade of experience guiding projects that bring together housing, economic vitality, small business growth, and placemaking. He has built a career at the intersection of real estate, nonprofit leadership, and civic service, helping communities unlock opportunity and design strategies that are both bold and practical.
At Rivers & Roads Consulting, Ross partners with organizations and municipalities to deliver economic development strategies, master plans, and revitalization initiatives that strengthen communities. His recent work includes feasibility planning for mixed-use development, technical assistance for towns across Maryland, and strategic consulting for nonprofits and associations. He draws on his experience in both the private and nonprofit sectors to guide clients through complex challenges — balancing vision with execution.
Previously, Ross served as Executive Director of Discover Easton, where he spearheaded the creation of the Chesapeake Fire & Ice Festival, expanded the town’s signature events, and re-accredited Easton as a Main Street Maryland and Main Street America community. He later led community development initiatives at a regional nonprofit, where he managed real estate development projects and advanced inclusive housing strategies such as Easton Crossing — a model that combines affordable, market-rate, and supportive housing into a single, integrated community.
Ross has also served as a licensed commercial real estate advisor, working with investors, developers, and municipalities to maximize the value of properties and projects. Earlier in his career, he founded a creative consultancy, helping businesses, nonprofits, and governments strengthen their digital presence and marketing capacity.
In addition to his professional work, Ross is deeply engaged in civic leadership. He is an elected commissioner in the Town of Hillsboro and has served on multiple boards, including Chesapeake Music and the Talbot Interfaith Shelter. His contributions to economic development and community revitalization have been recognized regionally, including being named to APG Media’s “Best Consulting Firm” list on the Eastern Shore.
Ross is known for blending data-driven strategy with community-rooted engagement, helping leaders move from vision to implementation with clarity, momentum, and impact.