The Pirates of Pinehurst: Sherwood’s Free Halloween Adventure

Photo courtesy of The Pirates of Pinehurst

Every October, a spirited band of neighbors in Sherwood, Oregon, transforms Pinehurst Court into a pirate’s paradise. Explore the special free attraction, The Pirates of Pinehurst.

What began as one pirate ship has grown into a whole neighborhood takeover, complete with animatronics, treasure hunts and weekend shows.

Here’s how you can join in on the swashbuckling spectacle of Halloween lights, displays and fun. 

If you’re looking for a display closer to home, don’t miss Davis Graveyard.

The Pirates of Pinehurst: Sherwood’s Free Halloween Adventure

Let’s explore each attraction: the street, the show and the hunt.

The Street: Pinehurst Court Comes Alive

Pinehurst Court—tucked at the intersection of Pinehurst and Woodhaven—is home to The Pirates of Pinehurst. Each October, the quiet cul-de-sac becomes a bustling pirate haven where 11 homes create themed displays worthy of the high seas.

This year’s displays include:

• Sirens’ Cove
• Pitcairn Island
• Port of Destiny
• Swan Island
• Blue Bayou
• Tortuga Tavern
• Dead End Lagoon
• Blackpearl’s Brig
• Botany Bay
• Rum Island
• Avila Blackwater Bayou

Take a stroll through the court to experience each pirate scene up close. Every display is viewable daily throughout October.

The Show: Jack Sparrow and the Pinehurst Gold

Join The Pirates of Pinehurst for an original 10-minute show that tells the thrilling tale of Jack Sparrow and the Pinehurst Gold.

This one-of-a-kind neighborhood production combines animatronics, lights, fog, sound, and video—all created and performed by the residents themselves.

2025 Showtimes

October 3-12, 2025

• Thursdays and Sundays at 7:30 and 8 p.m.
• Fridays and Saturdays at 7:30, 8 and  8:30 p.m.

October 16–30 (including October 29)

• Thursdays-Sundays at 7, 7:30 and 8 p.m.

Park near the intersection of Woodhaven and Pinehurst and walk down to view the show. Be sure to follow the pirates on Facebook and Instagram for daily updates and weather-related cancellations.

The Hunt: Find the Pirate Gold

Think you have what it takes to become a legend? Starting October 1, the pirates hide their gold throughout Sherwood’s trails and parks. Around 400 small doubloons and 15 large medallions await discovery—each hidden no more than 10 feet off the trail.

Every weekend, about 80 new pieces are hidden starting on Fridays. Search high and low, brush aside a few leaves and you might just strike gold.

When you find a treasure, post a comment on the pirates’ Facebook or Instagram so the crew can track what’s still out there. Bring your bounty back to Pinehurst Court on October 25-26 and 29-31 for your reward.

Organizers request only one piece of gold per kid. If you see another one, leave it be for the next person. 

Here’s the map:

All activities are free. The Pirates of Pinehurst is at SW Pinehurst Ct., Sherwood, Oregon. For more information, visit piratesofpinehurst.org and follow the adventure on social media.

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Looking for more Halloween events? Here’s a full list: