Experience the Eastham Windmill Weekend Festival 2023

The annual Eastham Windmill Weekend Festival will take place September 8th -10th, 2023 on the Eastham Town Green. Planned and organized by a dedicated team of local volunteers, this festival celebrates the history, warmth, charm, and community connection unique to Eastham and the Outer Cape. The theme of this year’s Eastham Windmill Weekend Festival is “Once Upon a Time.”

Some Facts about The Eastham Windmill

eastham windmill weekend festival

The Eastham Windmill, located on the Green in the center of town, was built in Plymouth, MA, around 1680. It was moved to Truro in the 1770s and then to Eastham in 1793 (first where the National Seashore Salt Pond Visitor Center is now located), and then to its present site in 1808. Lovingly restored and maintained, it is the oldest and last working gristmill on the Cape.

In Colonial times, gristmills were a vital centerpiece of community life in coastal towns. While many of us rediscovered the earthy joys of bread baking and sourdough starting while quarantined during the COVID-19 pandemic, bread baking back in the day was an arduous necessity. Farmers brought their grain to the local gristmill to be ground into flour for baking. Corn, not wheat, was the predominant crop here on Cape Cod, so many traditional New England recipes are built around cornmeal – think Johnny Cakes, Anadama Bread, Indian Pudding, and Brown Bread.

Vintage Cars, Local Talent, Touch-A-Truck, Parade, Live Music, Tricycle Race, and more Family Fun

Eastham locals consider the Eastham Windmill Weekend Festival the unofficial beginning of fall on Cape Cod. The festival attracts visitors who enjoy the fairs, festivals, and other small-town traditions that preserve the salty charm and culture unique to the Cape.

The Eastham Windmill Weekend Festival opens with a talent show on Friday night featuring a collection of performers from tiny dancers, school-aged martial artists, and magicians to first-rate local musicians. Be sure to stop by the Orleans/Eastham Elks Club for their annual fish fry before you set up your chair on the Green to enjoy the show.

On Saturday, the vehicle show opens at 10:00 a.m.. Car enthusiasts can stroll the grounds to view vintage and unique vehicles while chatting with owners happy to share the cars’ history and anecdotes about their path to ownership and restoration.

eastham windmill weekend festival

The Eastham Town Green will be bustling all day with live music, crafters and local artisans, children’s activities, and a booth featuring antique appraisals, so dig those treasures out of the garage and attic to see what hidden value they might hold. There will also be food! Mary’s Fine Food Provisions will be serving up cod cakes, pulled pork, slaw, and beans. Food trucks, fried dough, burgers, and ice cream will also be available if you are hungry for traditional fair fare.

The Great Tricycle Race takes place at 2:00 on Saturday afternoon. Trike-riders of all ages and sizes will race for the win and bragging rights on Depot Rd. next to the Town Green.

Touch-A-Truck, located on the Field of Dreams across from Windmill Green, is always a favorite among kids and big-rig-loving kids at heart.

Can I get an adult beverage at the Eastham Windmill Weekend Festival?

This year you can! For the first time, the Eastham Windmill Weekend Festival will include a beer and wine garden open from noon to 4 p.m. on Saturday featuring wine from Cape Cod’s Truro Vineyards and Hog Island Brewery.

Do You Love a Parade?

There is something about a small-town parade – beach chairs lining the streets, the middle school band trying their best at Yankee Doodle, dogs dressed as lobsters, and homemade floats built by neighbors and Scout troops.  Parade entries are designed around the 2023 parade theme – “Under the Sea.” Winners will be announced when the parade winds down at the Town Green.

Bagpipes Anyone?

eastham windmill weekend festival

Immediately following the parade, the Highland Light Scottish Pipe Band performs. Comprised of pipers and drummers ages 16 – 60 from Cape Cod and South Eastern Massachusetts, the band has been thrilling audiences with the traditional music and spectacle of the Great Highland Bagpipes and Drums for over 40 years.

Stroll Back to “Once Upon a Time” at the 2023 Eastham Windmill Weekend Festival

Welcome the calmer, cooler fall days with a beloved Outer Cape tradition, the Eastham Windmill Weekend Festival. This event is the perfect time for locals to celebrate their community and the gifts of small-town life and for Cape visitors to “play local” for the day and get a glimpse of year-round living in one of Cape Cod’s outermost towns.

Learn about more Historic Windmills on Cape Cod.




Please feel free to share your favorite Cape Cod experience about this topic with our audience!

This Post Has One Comment

  1. Remi

    Beware they don’t allow pets in the festival! Who does that seriously? Stay away if you love animals.

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