Business-minded residents of the Eastern Shore are invited to an exciting showcase of regional entrepreneurship at the 2026 Upper Shore STRT1UP Roadshow, hosted by the hosted by Washington College and StartUp Maryland, in partnership with Cecil County Economic Development, Kent County Economic Development, Queen Anne’s Economic Development, and the Upper Shore Regional Council. The pitch competition will take place on Tuesday, April 14, 2026, at 2 p.m. on the Washington College campus. Aspiring entrepreneurs from Cecil, Kent, and Queen Anne's counties will pitch their innovative business ideas for a chance to win significant cash prizes. This must-attend event brings together startups, students, business leaders, and resource partners from across the Upper Shore.
This is Washington College’s third year hosting the Eastern Shore competition. The College's Warehime School of Business was recently established to further Washington's commitment to providing a premier business education rooted in the liberal arts and is expected to begin accepting students starting this fall. The school’s mission aligns well with that of USRC’s focus on nurturing the physical, economic, and social development of the Eastern Shore. Both are invested in growing business opportunities throughout the region.
“We are proud to host this celebration of entrepreneurial energy for the third consecutive year,” said Caddie Putnam Rankin, associate dean of Washington College’s Warehime School of Business. “Competitions like this reflect the Warehime School’s commitment to experiential learning, regional partnership, and the advancement of innovative ventures. Seeing one of our own students earn top honors last year highlighted the depth of talent within our community, and we are honored to support an event that equips emerging business leaders with the resources, mentorship, and confidence to take their next meaningful step.”
This dynamic event is free to attend and offers a unique opportunity to witness the energy and creativity of local startups. Selected entrepreneurs will present 5-minute pitches, vying for a $4,000 grand prize. The second and third place runners-up will receive $1,500 and $500, respectively. Pitches will be judged on clarity of idea, business viability, problem-solving impact, and innovation.
In addition to the competition, attendees will benefit from the Business Resource Panel with a discussion focused on funding and incentives (panelists to be announced). This session will explore available capital resources, incentive programs, and practical funding strategies for startups and growing businesses. They’ll also have the chance to connect with key resource partners offering valuable support for entrepreneurs and small businesses. Organizations such as Maryland Capital Enterprises / Women’s Business Center, the Upper Shore Regional Council Business Mentor Program, TEDCO, and others will be on-site to share information about their programs, funding opportunities, and technical assistance.
Don’t miss this opportunity to experience the thrill of entrepreneurship and support local business growth. This event is free and open to the public to attend. For those wishing to compete, the deadline to apply to pitch is March 3rd at midnight. For more details and to apply to register to compete or just attend, please visit: https://www.kentcounty.com/strt1up.
About StartUp Maryland
Driven from within the startup community and led by/for entrepreneurs, Startup Maryland is peer-driven and focused on high-growth ventures. Forged on the themes spawned by national initiatives, Startup Maryland strives to connect innovation communities. We recognize the importance of founding - entrepreneurs, startup, ramp-up and speedup companies to the innovation economy. Startup Maryland rallies entrepreneurs, supporters, and other innovation stakeholders around four main mission themes: Celebration | Coaching | Curation | Capital. Learn more at www.startupmd.org
About Washington College
Washington College, Maryland’s premier small college, enrolls approximately 1,000 undergraduates from more than 39 states and territories and 23 nations. Washington is known for outstanding academics in more than 50 academic programs. With an emphasis on experiential learning opportunities across the disciplines, ranging from internships and research to international study and civic engagement, Washington prepares students for successful careers and lives after graduation. The College is home to nationally recognized academic centers in the environment, history, and writing as well as the 5,000-acre river and field campus which provides unique research opportunities for students and faculty. Learn more at www.washcoll.edu.
About Upper Shore Regional Council
The Upper Shore Regional Council (USRC) is a Maryland-based regional planning and development agency serving Cecil, Kent, and Queen Anne’s counties. It fosters economic growth, infrastructure development, and agricultural sustainability through initiatives like the Micro Ag Grant Program, the 3rd Annual Upper Shore STRT1UP Roadshow, and business mentoring. The council connects local, state, and federal resources to promote the region's unique, bucolic identity while boosting its economic relevance.
