Eastham Windmill Weekend 2026: A Cape Cod September Tradition
Looking for a fun Cape Cod event in September? Make plans for Eastham Windmill Weekend, taking place September 11–13, 2026, throughout Eastham, Massachusetts. This longtime Cape Cod tradition brings the community together for a full weekend of live music, food, crafts, family activities, a parade, a road race, contests, vendors and more.
Windmill Weekend is a celebration of Eastham and the end of the summer season, with many activities centered around the historic Windmill Green across from Town Hall. The weekend has been a beloved Eastham tradition for 48 years and offers plenty to see and do for both locals and visitors.
Bring the family to this fun Cape Cod Fall event.
📅 Eastham Windmill Weekend 2026
When: Friday, September 11 – Sunday, September 13, 2026
Where: Windmill Green and other locations around Eastham, MA
Admission: Many events are free
📍 Windmill Green
2405 State Highway, Eastham, MA
Additional activities take place at First Encounter Beach, the Elks Lodge and other locations around town.
🎉 Friday, September 11
The weekend kicks off Friday evening at the Elks Lodge.
🍗 Chicken & Fish Fry – 5:30–7:30 PM
🎤 Talent Show – 7:30–9:00 PM
The talent show is the official kick-off to the weekend, and performers are invited to show off their talents. The organizers recommend ordering ahead for the Friday night fish fry.
🚗 Saturday, September 12
Saturday is packed with activities on the Windmill Green and around Eastham.
🎶 Live Music – 10 AM–4 PM
🍔 Food Vendors – 11 AM–4 PM
🍺 Beer & Wine Garden – 12–4 PM
🎨 Craft Show – 10 AM–4 PM
🚗 Vehicle Show – 10 AM–2 PM
🚲 Historical Bike Ride – 10 AM–12 PM
🚒 Touch a Truck – 11 AM–1 PM
🏖️ Sand Art Contest – Registration at 3 PM; building from 4–6 PM
🧘 Yoga on the Green – 9:15–10 AM
🎟️ Free Kids Raffle – 10 AM–3 PM
💃 Line Dancing – 1:30–2:30 PM
The Sand Art Contest takes place at First Encounter Beach with this year’s theme, “Eastham Rocks!” and live music from Pans in Paradise.
The vehicle show is another popular part of the weekend, featuring more than 70 participating vehicles.
🏃 Sunday, September 13
Sunday brings even more family fun, including one of the weekend’s biggest traditions — the Eastham Windmill Weekend Parade.
🏃 Windmill Weekend 5K Road Race – 8–9:30 AM
💪 Group Workout – 9–10 AM
🎨 Craft Show – 10 AM–3 PM
🎟️ Free Kids Raffle – 10 AM–3 PM
🎺 Windmill Weekend Parade – 10–11 AM
🎶 Live Music – 11 AM–3 PM
🍔 Food Vendors – 11 AM–3 PM
🍺 Beer & Wine Garden – 12–3 PM
🚲 Tricycle Race – Following the parade
🎈 Don’t Miss the Windmill Weekend Parade!
The annual parade is one of the highlights of the weekend and features bands, floats, trucks, cars and plenty of candy.
The 2026 parade theme is “Eastham Rocks!”
The parade begins at 10 AM on Sunday, September 13, starting at Old Orchard Road and traveling along Route 6 to the Windmill Green.
🏖️ Windmill Weekend 5K Road Race
For runners, walkers and families looking to get active, the annual Windmill Weekend 5K starts and finishes at scenic First Encounter Beach.
📅 Sunday, September 13, 2026
⏰ 8–9:30 AM
📍 First Encounter Beach
The race welcomes runners and walkers of all ages and abilities. The scenic course travels along Samoset Road before looping back toward First Encounter Beach.
The 2026 race is also being held in memory of two Eastham neighbors, Kit and Jerry, with 50% of race proceeds being donated to the Kit & Jerry Foundation for Good.
👨👩👧👦 A Great Family Weekend on Cape Cod
If you’re looking for family-friendly things to do on Cape Cod in September, Windmill Weekend is definitely one to put on your calendar.
Kids can enjoy the Free Kids Raffle, Touch a Truck, Sand Art Contest, Tricycle Race and parade, while adults can browse the craft vendors, enjoy live music, grab something to eat and check out the vehicle show.
And of course, there’s the historic Eastham Windmill, an important part of the town’s history. The town describes it as the oldest and last working gristmill on Cape Cod, and it is listed on the National Register of Historic Places.
🚗 Parking & Shuttle Information
Parking at the Windmill Green is very limited, so plan ahead if you’re attending.
Saturday shuttle service runs from 10 AM–4 PM, with loops from First Encounter Beach and the Elks Lodge. There is also service from the Main Street Mercantile parking area, with shuttle times varying by location.
Tip: If you’re bringing the kids, checking the shuttle information before heading out can make your day a whole lot easier!
📍 More Cape Cod Events
Eastham Windmill Weekend is a great way to enjoy Cape Cod in September after the busy summer season starts winding down. Whether you come for the parade, crafts, food, live entertainment, kids activities or simply to enjoy a classic Eastham tradition, there’s plenty happening throughout the three-day celebration.
Save the date: September 11–13, 2026!