March 4th Update – 2026 Great Pirate Paint Off

/ josephforster86

Last Updated on March 5, 2026

We’ve finished the second month of the 2026 Great Pirate Paint Off and we’ve got some People’s Choice Voting happening now, and we have some end of month prizes to give away. Both the Oak & Iron and Terrain categories were incredible this year. Very impressive work!

Entry #8 - Bridgetown Street
Bridgetown Street by Ret T

We’re only halfway through the contest and we’ve already surpassed last year’s total entries. It’s great to see stuff getting painted and crafted.

For full details on schedule and rules for the contest, visit this page.

End of February Prizes

We give away some prizes and the midpoint and endpoint of every month. Most of these prizes are drawn at random from qualifying entrants while the People’s Choice voting will determine the winners of each category. Today we are giving away:

Finally, we will have People’s Choice voting up for both Terrain and Oak & Iron categories, running until the end of the day Friday, March 6th. Prize medals will be awarded for the top placing entry in each category.

Kraken Set from Timber & Sail

Created and donated by Jason Klotz, this Kraken model is sure to add some massive spice to your Oak & Iron games.

This prize goes out to a random participant in the Oak & Iron category, one chance per person. We had 26 entries from 13 painters in the Oak & Iron category.

Oak & Iron Winner

And our winner is Derek S! Derek painted up one of Firelock newest Oak & Iron ships, the Galley Frigate:

This prize is a 3d printed set of a Kraken, 10 tentacles and a movement base. Full rules, cards, and even rules for solo play against the Kraken can be downloaded from Timber & Sail.

Jason has done a huge service to the Oak & Iron community with his Timber & Sail page and he has an increasing number of high quality STL’s available for both Oak & Iron and Blood & Plunder. If you dabble in the darks arts of 3d printing, checkout his Cults3d page and pick up some of his excellent designs.

Thank you to Jason and Timber & Sail for supporting the contest with this prize donation!

Terrain Kit from Things From the BAsement

The Terrain category really took off this year with more than 100 entries! For comparison, we had 35 Terrain entries last year. For this category we are giving away a MDF Spanish House kit from Things from the Basement.

Things from the Basement has a couple series of 28mm building kits that are perfect for Blood & Plunder use, most notably their Mediterranean Village set.

Terrain Winner

And our winner for this prize is Peter J! Peter is a great painter who has participated in the Great Pirate Paint Off over several years. Peter’s entry for terrain this year is one of the prizes from Stone Temple Studios from the Summer of Plunder last year!

And Peter has completed his entry for Dexter’s Plunder Den Terrain Flash Challenge (which is ongoing until March 15).

Montgomery entered several characters as well, along with a beautiful Oak & Iron ship. Congrats on the great work and the paint set prize!

Plunder Den Terrain Flash Challenge – 2026 Great Pirate Paint Off

A huge thanks to Things from the Basement for helping subsidize this prize this year!

1 Reale Coin Fortune Token

These next three prizes are drawn at random from all entries from the month. So the more entries you submit, the better chance you have of winning something! These are some fun little accessories from our Blood & Pigment shop.

Our first little prize we’re sending out is a 1697 1 Reale coin reproduction from St. Augustine Mint. This is a small but authentic and beautiful handmade coin that we love to use as Fortune Tokens for Blood & Plunder, Oak & Iron, or Port Royal.

Chosen at random from the 131 entries, Dave B is our winner! Dave entered a whole fleet of Oak & Iron ships, and sets of terrain for both Blood & Plunder and Oak & Iron. Great work in quantity and quality!

Blood & Pigment Turn Counter D6

We’re happy to have a couple fun Blood & Pigment branded items to give away this year! First we have a bone d6 turn counter die.

These are made of real bone and their extra large size makes them great turn counters for your 6 turn Blood & Plunder games. And the winner for this prize this month is Gerardo G! Congrats to Gerardo. He has submitted entries in nearly all categories so far, most recently these Birchbark canoes.

Blood & Pigment Set of D10’s

We recently worked with Baron of Dice to get a set of d10’s made with our logo on them. They make us feel cool and we hope you enjoy them!

The winner for this prize for January is Carlos MG! Carlos won the 1 Reale coin last month, and has won again! He entered some fantastic entries, with the Spanish Mission terrain catching my eye.

Entry #2 - Spanish Mission Church

Congrats to Carlos and we hope those d10’s roll high!

Disclaimers, Excuses & Apologies

Our apologies for the lateness of this article. Life circumstances (including a lot of overtime and a totaled car) piled up and delayed the publication of this post.

Also, we have to acknowledge an unfortunate error we made in the Oak & Iron category. An excellent entry from Michael P was mistakenly omitted from the Oak & Iron gallery during voting. An unfortunate combo of software glitches and human fallibility unfairly took this entry out of the running and we apologize. We are sending off some bonus goodies to the painter of this worthy entry,

Final Thoughts

Marooned Blundermonkey by Jason Ropp

Congratulations to all the winners here at the end of the month. That’s all we’re going to cover in this post, but watch for more updates on the painting contest coming soon. Posts you can expect to see in the next couple days:

  • Another post spotlighting more of the great entries during February
  • A post discussing the Port Royal and Blood & Plunder Unit categories and detailing the prizes to be given out in March

Again, make sure to peruse all the entries in the mega gallery, or focus on the Oak & Iron or Terrain in their respective galleries.

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