[9]) The winner of the inaugural Maryland Cycling Classic on Sunday, September 4, 2022 was Sep Vanmarcke of Belgium riding for Israel-Premier Tech with a time of 4:34:45.

[11] The cycling race is part of a four-day weekend community celebration of healthy lifestyle and living with participatory events, festival with interactive exhibits, local foods and drinks along with other fun activities.

The Maryland Cycling Classic also includes the charity Bridges of Hope Ride Presented by Kelly Benefits,[12] which provides the opportunity for cycling enthusiasts to ride sections of the Maryland Cycling Classic (MCC) course the day before the pro-cycling event, while raising funds for the UnitedHealthcare Children's Foundation (UHCCF).

"[10] The 2023 Maryland Cycling Classic supported by UnitedHealthcare took place on Sunday, September 3, 2023.

The 2024 race was cancelled following the Francis Scott Key Bridge collapse in March 2024 which heavily impacted traffic in the Baltimore region.