Here at Cape Charles Main Street, we host three signature events to promote our community in the off-season. These events promote vitality of the town and community-wide spirit for our residents and visitors. Our three signature events are….

LOVE Run
LOVE Run incorporates Cape Charles and Virginia’s sense of love with our adoration for the outdoors. At the LOVE Run, participants can compete in the 10k, 5k, or 1 mile race. The course will take you through historic downtown Cape Charles overlooking the Chesapeake Bay. All participants can opt in to be sprayed with bright, fun, harmless, and environmentally safe colors. Additional race-day fun includes a kids’ dash and wheelchair accessible race.
LOVE Run 2026 TBA.

LoveFest
Hosted alongside Citizens For Central Park, LoveFest offers attendees soothing music and vibes as the ’60s come back to life for one night only! Get your flower power, tie-dye, and go-go boots ready to dance the night away and don’t forget about the Best ’60s Costume contest!
August 30th | Central Park

Festive Fridays
From Thanksgiving through Christmas, experience Cape Charles’ holiday charm and enjoy many FREE Friday night festivities for the whole family. Activities include horse-drawn carriage rides, movies at the Historic Palace Theatre, petting zoos, live music, and more!
Festive Fridays TBA.