Oak Bluffs • Martha's Vineyard
Welcome to the first annual Vineyard Classic 5K, a celebration of community, movement, and the breathtaking beauty of Martha's Vineyard. Our USA Track & Field certified course winds around the stunning East Chop Bluffs, giving every runner a race experience unlike anything else on the island. Whether you're a seasoned runner or lacing up for the first time, this race is for everyone. Bring your family, breathe the sea air, and be part of a brand new island tradition.
This 5K is certified by the USA Track & Field Association — accurately measured and officially recognized.
Every mile of this course offers something special — from historic streets to a refreshing seaside stretch to the vibrant energy of the open air markets at the finish.
Oak Bluffs Harbor on Lake Ave — the heartbeat of the island. Your race begins and ends here.
Head out along the iconic East Chop Drive with stunning views of the harbor and open water.
Catch your breath and hydrate at the first water station as you round toward the lighthouse.
Wind up toward the East Chop Lighthouse — the crown jewel of the course and a photo-worthy moment.
Refuel at the second water station as you head back through the tree-lined interior.
Cross the finish line near Oak Bluffs Harbor surrounded by the energy of the open air markets. You earned it.
Your official number for race day, included with every registration.
A Vineyard Classic keepsake shirt — a perfect island memento to remember the day.
Refuel after the finish line with post-race refreshments provided to all participants.
Open to all ages and fitness levels. Walk, jog, or run — everyone belongs here.
A portion of all proceeds from the Vineyard Classic 5K will be donated to a local Martha's Vineyard charity. When you register, you're not just running for yourself — you're making a difference for the island community we all love.
Supporting the island
we love.
Secure your spot in the inaugural Vineyard Classic 5K. Race bib, shirt, and post-race refreshments are all included. Space is limited — don't miss the island's newest race tradition.
We're grateful to the businesses and organizations who help make this event possible.
Interested in sponsoring the Vineyard Classic 5K? Get in touch.