Sister Cities International (2021) defines a “sister city” or “twin town” agreement as a long-term partnership between two communities in two countries that is officially recognized after the highest elected officials from both communities sign an official document decreeing their partnership. Since the launch of President Dwight D. Eisenhower’s People to People program in 1956, sister cities practice citizen-led, people-to-people cultural paradiplomacy: subnational and nongovernment cultural initiatives within two officially linked communities. However, sister cities established towards the end of the 20th century shifted to regional trade initiatives, prompting more government involvement. The 21st century saw a decline in government involvement and funding for sister cities in the US, prompting a return to citizen to citizen paradiplomacy, and in turn a return to the artistic and cultural initiatives intrinsic to the sister city format. The visual and performing arts were intrinsic to the establishment of the modern incarnation of sister cities: as funding and municipal support continues to decline for these community partnerships, the volunteers who run these culture programs from within the community are inspired by and rely on the arts and shared lore of their local communities in order to maintain their sister links through artistic exchange activities, including the visual and the performing arts. This is certainly the case for the Maine-Aomori sister state relationship, which has shifted its programming away from the program’s long withstanding regimen of student and delegation exchange initiatives to focus on visual art exchange initiatives and an art residency program during the last decade. This article suggests that US-Japan sister cities which operate predominantly without government support like the Maine-Aomori relationship tend to rely on artistic exchange: this denotes a return to the seminal grassroots model of paradiplomacy modeled by early sister city activities and the seminal People to People program that relies on local culture for citizen engagement, recruitment, and communication between sister cities.