Join us for the 2026 Annual Windmill Weekend Road Race! Join us on Sunday, September 13, 2026 for the annual Eastham Windmill Weekend Road Race, a beloved Cape Cod tradition that brings runners, walkers, families, volunteers, and neighbors together to celebrate community and tradition. This scenic 5K welcomes participants of all ages and skill levels . The race begins at beautiful First Encounter Beach , travels through the rolling hills of Eastham’s Samoset Road, continues past the Eastham Library, and returns back to First Encounter Beach. A longtime favorite for many and an enjoyable race for all! This year’s race holds special meaning as we dedicate the event in memory of two beloved Eastham neighbors, Kit & Jerry, who were known throughout the community for their kindness, generosity, and dedication to others. In their honor, 50% of race proceeds will be donated to the Kit & Jerry Foundation for Good , helping continue the spirit of kindness and giving back that they shared with s
Hotels Near This Race
Find accommodation close to the start line in Eastham, MA. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
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Race Travel Insurance
Don't forget travel insurance for September 13.
You've trained for months and booked a trip to Eastham, MA.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
