Win Tickets ($150): 2026 Swashbuckler’s Ball @ Milwaukie Elks Lodge #142 | Portland’s Pirate Prom
We are giving away a pair of tickets to the 2026 Swashbuckler’s Ball @ Milwaukie Elks Lodge #142 on January 17. To win, comment below on this post why you’d like to attend. Winner will be drawn and emailed January 12.
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From our sponsors:
2026 Swashbuckler’s Ball
January 17, 2026
7pm – 12am | $75+ | 21+
Purchase Tickets: swashbucklersball.com
Milwaukie Elks Lodge #142
13121 SE McLoughlin Blvd, Oak Grove, OR 97222
Raise your mask and ready your cutlass – The Swashbuckler’s Ball returns for its 14th grand celebration! On Saturday, January 17th, 2026, the Portland Elk’s Lodge #142 transforms into a Venetian dream of silken masks, golden lanterns, and high-seas revelry. Join pirates, buccaneers, and mischievous rogues for a night of dancing, feasting, and finery fit for the courts of Tortuga and Venice alike.
Featuring live entertainment from…
- CHERVONA: The ultimate International Folk and dance party machine! ● COMING UP THREES: High-energy, Celtic-inspired, pint-raising Irish pub band.
- BELTAINE: Original and traditional music inspired from Celtic, folk, rock and classical sources.
- BERGAMOT BURLESQUE: An impressive troupe of performers and their signature sultry nautical burlesque shows.
- BIDDY ON THE BENCH: Irish rebel songs & shanties, lively session tunes, and mournful Gaelic ballads.
- THE SCUPPERMONKEYS: Seattle-based Irish band inspired by the tunes of Ireland… but with a pirating habit they just can’t kick!
- THE PILLAGE PEOPLE: Bringing the high seas to life with live pirate music, rousing sea shanties, and comedic parodies of classic songs—performed with piratical flair!
Plus…
NEW BARS!
Delve belowdecks and make yer way through the maze of the ship’s hold. If yer lucky, you’ll stumble into a hidden tavern for a pint. We’ve designed new themes for the Belowdecks bars this year. Can you find them all? Don’t worry, we’ll give you a map!
MORE STAGES!
Dance the night away at the Quarterdeck Stage, hoist your tankard at TWO Belowdecks stages!
MORE GROG!
Custom cocktails themed for each bar and made especially for the evening. Plus a variety of ale, cider, and more!
MORE VENDORS!
An expanded row of piratical merchants! Spend yer hard-plundered coin in The Market.
MORE PHOTOS!
Capture your revelry with our fabulous photo booth. There’s room for yer entire crew!
Ticket Pricing:
- VIP tickets: (limited quantity, pre-sale only): $150 each
- General Admission: $75 pre-sale, $85 gate
Each VIP ticket includes:
– A single reserved seat at a table in the VIP reserved area
– Two-hour early entry into the event (doors for VIP ticket holders open at 5:00 PM)
– Access to the Admiralty Feast, a private VIP-only dinner (5:00 PM – 7:00 PM) – TWO drink tickets
– TWO raffle tickets
– 2025 Swashbuckler’s Ball event poster
– 2025 Swashbuckler’s Ball exclusive commemorative gift
– Complimentary coat check
Each GA ticket includes:
– Entry at 7:00 PM
– Access to all stages and bars in the venue
Tickets are Non-Refundable
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My pirate alter ego (Valkyrie) has been wanting to attend this event for several years now, but it just hasn’t been in the cards. It’d be hard to have an excuse to not go with a pair of tickets won on pdxpipeline!
A ball like this looks fun to go to.
I would love and opportunity to dress up!
this sounds totally wild and totally fun!
I’m a pirate at heart and this sounds much bett’r n a getting scurvy.
Rawr matey!! Shall be a good night of plundering and winching..count me in!
I need to be here, so I can find a pirate booty that shivers me timbers… said the single lady over 50… getting my groove back like Stella, and embracing my golden girl era…but still have a nice treasure chest.
Ahoy!
Aye Mate!
Well oil Beef Hooked!!! lol
Now say that one quickly! lol
My husband and I love dressing up as pirates and would really enjoy going to this.
I’m married to a pirate who transforms our front yard into a pirate ship at Halloween – would love to take him on a date to the Ball 🏴☠️
Polly was so disappointed we didn’t win tickets last year for this that she molted until she looked like a plucked chicken – Sure hope we don’t get scuttled this year… I’d hate to watch her shiver her timbers again all winter!
In true pirate fashion I should thieve some tickets to get in, but if I win them that would be okay too 😛🦜🏴☠️
Some secrets are best kept behind a mask. Not all adventures happen at sea…some begin under lantern light, carried by music, laughter, and a shared sense of mischief and argggg. Life needs more moments that feel legendary!!
This is one of my favorite events to break up the post-holidays SADD. I’m so depressed to not have the money to go this year. This mer-pirate has to spend her trinkets on bills 😭
I’d love to be able to win a pair of tickets and take my partner! We love to dress up but neither of us have been to the Swashbuckler’s Ball before! 🏴☠️
Argh! We Have had a land lubbers luck setting our sails for this adventure! may the winds be at our backs, a grog in hand, and a hearty song in the air this time me hearties!
A pirate prom- heck yeah!!
I’ve got the costume ready to go and friends to celebrate with. a few years ago, I attended this event and learned much about the history of pirate culture, the dye for their clothes, blacksmithing on ship (people sported authentic belt buckles), and so much more.
A smart, curious pirate here wanting to dance and learn with the other goofballs.
Gyarr ya serious?!
This sounds neat
The year was 1691 when I was sucked into a vortex at sea… I was the only survivor from my crew, and when I came to, the world felt… different. I was transported into this here time. And though there’s plenty to like about this new world I find myself in, (access to showers, fruit, and fancy leg prosthetics) I miss me original time. The chance to go to the ball might be my one shot at nostalgia. Will ye give thee ol pirate a chance at happiness?
I’ve never gone to a dance with a partner and now that I have one, it would mean the world to me to go to a ball… especially a pirate themed one!!!
Last year I went as a scallywag, this year I want to go full capt Reagal. This event was incredible and would love another chance to go!
I’d love an opportunity to costume up and battle the winter gloom with a party!
Looks like a great time!
Arrrg you kidding me, matey?!? I’d love to attend.
I would love to attend with my dad who has been a pirate for 72 years!!
Be fun!!
SWASHBUCKLE ME UP! I would love to go and find some new things to do.
Been thinking of joining Elks Lodge for years — and attended Pirate Festival for 10+ years.
Calling in some salty sea dog fun.
Always wanted to see a pirate in person.
I’ve never been – but I’ve got all the things I’d need to fit right in. Can’t wait to hear this music!
YARRRR!!! Me matey and I just commandeered some swashbuckling good pirate gear and we’d love to show it off!
I want to attend because I do not have enough chances to wear all my pirate gear!
The familiar warm faces both visiting and working there booths with everyone wrapped up in their favorite bling. And yet it doesn’t feel like a stuff over expensive gala, rather it is just the right touches everywhere and feels like a welcoming family reunion.
Since I moved to Portland this has been an annual tradition with my best friends. I am hoping to keep the tradition going this year!
Warm familiar faces both visiting and at the booths all wrapped up in their favorite bling feeling like a large scale family reunion. Treasured by all who attend.
I’ve wandered ye hallowed halls once before and haven’t been able to pursue the pirate lifestyle again since due to lack of treasure. Would love the chance to attend argggh-gain!!!
I really want to win these tickets so that I can attend the event with my best friend of 20 years! She’s a single mom battling mental health and pirating is one of her few escapes! She’s never been to any of the pirate events and has only dressed up and gone pirate plunders at local bars with me! This will give her an opportunity to really dive into the pirate world and meet so many more wonderful pirates!
Swashbucklers unite! I want to swab de deck. Duke CanonBALLS
We’d love to go!
Can’t wait for my timbers to be shivered….Yes please
I was born a little pirate boy in the Nuttiest of Norths, so ppd confiscated me vessel and all of me treasure, arr. I have taken a very fine wench from a local pub, I wish to charm to pieces her with a once in a lifetime adventure in the Land of Port, your event shall have her eating out of the palm of my hand, she will surely join me in taking back what is mine. I demand entry, with all of my dearest regards. 🏴☠️
omg this sounds AMAZING. I would love to go!!!
Me and my fiancé are a good addition to the crew! We like to run a tight ship and would love to attend the ball. ARGHHH!
This looks so fun! Would be an awesome birthday outing!
This sounds like a lot of fun.
i’m already gonna spend that night dressed like a pirate in my own living room, might as well do it with other people dancing
My pirate garb’s been collecting dust. Looks like I have a reason to wear a wench costume again!
unmoored and adrift, help this Seattle pirate and her mermaid lover find friendly waters again. We’ll be in Portland that weekend and a nice of dancing and revelry sounds like a fun jaunt!
An evening among Portland Pirates is what dreams are made of. Ready to swap my prosthetic for a peg, just give a reason! 🙂
Would love to spend an evening among pirates!