For over 40 years, Eastham Windmill Weekend has been the town’s most anticipated end-of-summer event. After a two-year hiatus because of the CoVid-19 pandemic, the festival is back on in 2022 at Windmill Green and other venues around the community.

This year’s festival theme is “Once Upon a Time,” and the event is sure to be more popular than ever after taking a couple of years off. There will be live music, vendors, a parade, a talent show, and a car show, giving visitors plenty of opportunities to experience some of the fun.

Here’s a look at what you can expect when attending the 2022 Eastham Windmill Weekend on September 9, 10, and 11 during your Cape Cod vacation.

Friday, September 9

The festival kicks off on Friday, September 9, with a talent show at the Elks Lodge on McKoy Road. This show will highlight some of the best local talent the Cape has to offer and feature six or seven different performers during its 90-minute duration.

This show will take place outdoors at the Lodge’s pavilion and has a professional sound system that makes it a wonderful experience for attendees. There’s also a fish fry at the Elks Lodge earlier in the evening, so you can head down for dinner if you wish.

The talent show begins at 7:00 PM and is a great way to start Eastham Windmill Weekend.

Saturday, September 10

Saturday is far busier than the Friday evening, featuring multiple events throughout the day.

First, there’s a concert series at Windmill Green, which starts at 10:00 AM and runs until 4:00 PM. Bands playing at the concert include Rock Harbor 3, Toast and Jam, the Sarah Burrill Band, and The Dirty Water Dance Band, providing a full day of music for the entire family.

The music is accompanied by an artisan market, some food vendors, and other booths giving you the perfect opportunity to buy some souvenirs of your time on Cape Cod.

You might want to grab a raffle ticket or two while checking out the festivities because it offers the chance to walk away with some prizes. Available prizes in 2022 include an original painting by Robin Wessman, a $500 Ace Hardware gift certificate, and $100 gift certificates to various local businesses. Tickets are $3 each, four for $10 or ten for $20.

Saturday is also when the Eastham Windmill Weekend Vehicle Show takes place. This event is at the Elks Lodge and attracts nearly 100 classic and exotic cars to Eastham. It’s worth checking out if you’re interested in rare vehicles or simply want to see what local car lovers are driving.

The car show is free to attend, and first, second, and third place trophies are given out to some lucky participants who show up with the best-looking cars.

If you can only make one day of Eastham Windmill Weekend, it should be Saturday.

Sunday, September 11

Eastham Windmill Weekend finishes up on the Sunday with a parade, more music, and more food.

The parade starts at noon, where Old Orchard Road meets Route 6 near Arnold’s Lobster and Clam Bar. It then heads south on Route 6 before ending at Windmill Green at about 1:00 PM.

From there, the music begins at about 1:30, kicked off by the Highland Light Pipe Band. The concert series will finish with a performance by American Idol top 50 finalist and Eastham resident Natalia Bonfini.

It’s easy to wander in and out of Eastham Windmill Weekend because the events run all weekend long. Checking out Eastham on the September 9-11 weekend ensures you’re in town for some of the action.

Enjoying Your Time in Eastham

Although Eastham is one of the Cape’s smallest towns, there’s plenty to do in this community throughout the year. The area might start slowing down a bit in September, but the weather is still great, and events like Eastham Windmill Weekend provide abundant entertainment.

Book your vacation rental in Eastham if you’re heading to the region in September to ensure you don’t miss out on this wonderful end-of-summer event.