February 16 Update – 2026 Great Pirate Paint Off

We’ve hit the midpoint of February and we have some drawings for prizes from the Terrain and Oak & Iron categories for this year’s Great Pirate Paint Off. We would like to thank all the great painters participating in the contest this year. Last year we had 304 entries for the entire contest and we’re at 306 entries at less than halfway through!

But before we get to the prizes, we want to highlight The Plunder Den Terrain Flash Challenge! Dexter from The Plunder Den YouTube channel is running a special little contest through March 15. He’s provided a terrain building tutorial video for you to work from and he’s offering a pretty big terrain prize to the top participant. Check out further details in the video below or this page. We’ve already seem some projects started and they are looking good!

Mid Month Prizes

Here at the midpoint of the month we are giving away one set of Oak & iron Dice from Baron of Dice, and a Spanish Two Story House kit from Things from the Basement.

Terrain Entries

Our Terrain entries are really up this year with 68 entries at the middle of the month (total of 40 Terrain entries last year). These entries come from 23 different painters. Here is a sampling of the Terrain entries so far:

You can peruse the entire gallery of Terrain entries here.

Each of the 23 current contestants receives one chance for the prize, regardless of how many Terrain entries they have submitted.

Terrain Prize – Spanish 2 Story House from Things from the Basement

And this prize goes out to Derek T! The Lethbridge Crew is making a great showing in this contest so far!

From Derek’s entry:

“Some heavy jungle cover. The goal was to make a piece of terrain from dollar store items for less than $10. Came in around $8 all in with plenty of terrible dollar store fake plants left. Picture with my newly painted militia.”

Making terrain on a budget is a good challenge!

Congrats to Derek! We will be sending him the 2 Story Spanish House Kit from Things from the Basement.

Thanks to Things from the Basement for helping provide this prize.

Oak & Iron Entries

Oak & Iron ships are small, but they’re actually a lot of work! But with careful attention to detail, they look amazing, especially the new sculpts of the Galleon, 3rd Rate and Galley Frigate.

We’ve had 15 Oak & Iron entries so far from 7 different painters. Check out some of the entries so far:

You can check out the entire gallery of Oak & Iron entries here.

Each of the 7 current contestants receives one chance for the prize, regardless of how many Oak & Iron entries they have submitted.

Oak & Iron Prize – Set of Oak & Iron Nationality Dice from Baron of Dice

And our winner is Brandan K! Brendan has pretty much painted up an entire starter set these past two weeks! With the entire fleet painted up, he was able to submit the whole set as a “Force” for the end of the contest.

Congrats to Brendan! We will be sending a Oak & Iron Dice set of his choice as a prize.

Thanks to Baron of Dice for helping provide this prize.

Upcoming Deadlines & Prizes

Don’t forget to get started on your Plunder Den Terrain Challenge! Deadline is March 15. The prize is a handbuilt piece of terrain from Dexter.

The Oak & Iron and Terrain categories will be closing at the end of February and we will run a people’s choice contest to determine the winner to receive prize medals.

House by Matthias Van Dyck

The end of month prize drawing for Terrain is a pair of MDF Terrain Kits from Things from the Basement.

The end of month prize drawing for the Oak & Iron is a Kraken monster set from Timber & Sail.

Also, at the end of the month, we will be giving away a 1 Reale Coin from St. Augustine Mint, a set of Blood & Pigment D10’s, and a Blood & Pigment Turn Counter D6 to random entries submitted during February (regardless of entry type).

Please consider supporting our great February sponsors by purchasing cool stuff from them!

March’s categories are Blood & Plunder Units and Port Royal models.

Final Thoughts

Get back to painting! It’s been great to see such high participation this year, and we are please with the stepped quality the work as well. It’s an inspiration to us all to see models come to life with the power of pigment!

Oak & Iron Galleon by Riley F

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