For $25, runners can register for the Eastham Windmill Weekend Road Race, a 5K event scheduled for September 13, 2026 in Eastham, Massachusetts. The race starts at 8:00 AM at 1620 Samoset Road. This early-morning start time allows competitors to complete their run during cooler morning conditions. The flat 5K distance makes it accessible to runners of various ability levels, from those building fitness to experienced racers looking for a quick workout.
From the Race Organizer
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 so many. Whether you run, walk, volunteer, or cheer from the sidelines, we invite everyone to come together to celebrate community, tradition, and the lasting impact of kindness . Race Information: The race begins at 8:00 AM. Registration & Bib Pickup: Bib pickup and registration will be offered the day prior at the Eastham Windmill Green from 2:00–4:00 PM. Please note: Registration will NOT be offered in person on race morning. Online registration will remain open until 7:00 AM on race day. Bib pickup will also be available the morning of the race. Participants are encouraged to arrive at least one hour before the race to check in and prepare for an on-time start. We run rain or shine! General Race Entry Includes: Free beach parking Race entry Professional race timing Official race t-shirt for the first 75 registered participants T-Shirts: Participants must register by August 1st to be guaranteed their correct t-shirt size. Awards: This race will be professionally timed, with awards presented to: Overall 1st Place Male & Female Winners 1st Place Winners in each age group Parking: Free beach parking for participants and spectators will be available at both: First Encounter Beach Lot Bee’s River Lot Please note that parking is limited, and carpooling is encouraged whenever possible. We can’t wait to see you all for another memorable Windmill Weekend Road Race! Eastham Windmill Weekend Committee
Hotels Near This Race
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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
When is Eastham Windmill Weekend Road Race – 2026 2026 — Eastham, MA?
Eastham Windmill Weekend Road Race – 2026 2026 — Eastham, MA takes place on September 13, 2026. The race is held in Eastham, Massachusetts.
Where is Eastham Windmill Weekend Road Race – 2026 2026 — Eastham, MA held?
Eastham Windmill Weekend Road Race – 2026 2026 — Eastham, MA is held at 1620 Samoset Rd in Eastham, Massachusetts.
Where can I find hotels near Eastham Windmill Weekend Road Race – 2026 2026 — Eastham, MA?
RaceHotelFinder shows hotels sorted by distance from the race venue in Eastham. Use the map or list view on this page to compare options and book race weekend accommodation.
