Grand Opening Block Party


Grand Opening Parade 9/29 5:30PM

The EMERALD BAGPIPERS OF CHICAGO  paraded from Front St. and  rounded the corner of Duval and Southard  to the cheers and applause of hundreds of Irish pub  enthusiasts.


Grand Opening Block Party

EMERALD BAGPIPERS OF CHICAGO played a rousing concert after the parade and again all night long, every time the Zack Seemiller band took a break or every hour or so throughout the night.  The street was filled with partiers, Sweeney’s Weenies, Budweiser beer truck, and the stage for the Zack Seemiller band.  Mel T of the Hoebee in the Afternoon Experiment on 99.5 was the mistress of ceremonies and kept the party going.  Beer and drinks flowed from the porch and alley as well as from the Irish Oak Barrel’s two bars. Twenty one TVs showed the games. Irish songs and dance in the Irish Oak Barrel pub lasted until after three.  In short it was a great party and a great grand opening to Key West’s new traditional Irish pub.


Piping All Night Long

The Emerald Society Bagpipers entertained our patrons many times during the night and even after the block party had cleaned up and departed the partiers in the pub still enjoyed their playing.

Conor McGregor v Khabib Nurmagomedev


Conor McGregor UFC 229 match

Our prediction was: There’s intrigue and bad blood brewing against Conor on the challenger’s side. This fight could be the biggest in the history of the sport. Khabib is undefeated. Conor if 24/21. It’s worse than a grudge match.     We were right. Conor and his team had bad words to say about Khabib.  Khabib wasn’t happy.  The only time Conor could be the aggressor was when he was on his feet.  That wasn’t often.  Khabib had him on the mat virtually the entire 4 rounds.  In the fourth round Khabib put a choke hold on Conor that turned his head new colors.  Conor tapped out and the match was called by submission.  Khabib then flew over the fence into the crowd and started fighting on the Conor team.  It was a mess.  The organizers were not impressed and there was no celebratory arm raising in the octagon.

No Cover charge

Everyone had a good seat and a good view.

VIP Seating

Sold Out

It's going to be a party

Yes it was.  Check out the 25 minute Facebook video.

The Irish Oak Barrel invites the Navy, and all armed forces



The Irish Oak Barrel invites the Navy, and all armed forces to attend the Notre Dame vs Navy football game on October 27th.  

The tailgate party will begin at noon.  There will be surprise food guests.  There will be drink specials and FUN!

The tailgate party will begin at noon.

Tailgating will start at Noon on the 25th,26th and 27th

There will be surprise food guests.

There will be drink specials and FUN!

$3 Irish Paddy 

$5 Guinness 

$5 Jameson 

$5 Tullamore Dew 

$25 Jameson flights

Live Music

The Salty Crack Irish band will be playing all your Irish favorites on the 27th at 8PM!  Come sing along!

Party on until the wee hours of the morning!


Happy 243rd anniversary to the U.S. Navy Department


The United States Navy actually has two birthdays—one today October 13th, leading up to the Revolutionary War, and one April 30th, when Congress used its Constitutional power to officially create the Department of the Navy.  The Navy in its earliest form dates back to 1775, when it was established by the Continental Congress on October 13 in session in Philadelphia. The Navy considers this as its official birthdate.  However, after the Revolutionary War, the new nation sold its ships and sent its sailors home. It wasn’t until 1789 that the newly ratified Constitution empowered Congress to bring the Navy back.  Article I, Section 8 of the Constitution allowed Congress "to provide and maintain a Navy" as part of its enumerated powers. In Article II, the Constitution named the president as the commander in chief of the Army and the Navy.  It took until 1794 for Congress to approve money to buy new ships. Relations with the British, French, and Barbary pirates forced Congress to plan to build six frigates. Three of the ships were completed before hostilities died down: the USS United States, the USS Constellation, and the USS Constitution.  The start of the Quasi-War with France in 1798 led to the official creation of the Department of the Navy on April 30. The undeclared war on France involved raids on U.S. merchant vessels by French privateers and warships (which were too weak to take on British shipping).  Benjamin Stoddert, the first secretary of the Navy, played a critical role in establishing the new Navy. He secured funding for more ships, sent the Navy on attacks against the French in the Caribbean, and made sure the best officers and sailors were in the service. Stoddert also set up the first six Navy shipyards in the country.  Stoddert left office in 1801 as the Federalists were removed from power and Thomas Jefferson took over as president from John Adams. Although funding for ships was scaled back, Jefferson sent the Navy to the Mediterranean to protect American interests against the Barbary pirates in Tripoli and other areas. It fought well using the tactics adopted under Stoddert.  But in the War of 1812, the Navy was undersized compared with the British, which had the largest, finest naval forces in the world. While the Navy had several isolated, spectacular victories over the British, it couldn’t stop the empire from imposing blockade conditions.  Even worse, British forces were able to land in Washington, D.C., burning the White House and even the U.S. Navy Yard. At the war’s end, it became apparent that an active Navy was needed to protect merchant shipping, at the very least.  Since Stoddert’s appointment in 1798, there has always been a secretary of the Navy.  The secretary was a member of the president’s cabinet until 1949. Currently, the secretary serves in the Defense Department.  A civilian is appointed as the secretary of the Navy. Currently,  Richard V Spencer, a Marine, is the secretary.  In the past, historian George Bancroft served as secretary and played a key role in establishing the Naval Academy at Annapolis in 1845.  

Bancroft came into office about one year after the USS Princeton disaster of 1844. Secretary of the Navy Thomas Gilmer and the former Navy secretary (and active secretary of state) Abel Upshur were killed when a gun exploded on the Princeton during a demonstration.  Secretary Gilmer had only been in office for 10 days. His predecessor, David Henshaw, escaped the Princeton tragedy because Congress didn’t approve his recess appointment by President John Tyler. 


The Gorgeous G-string Competi

Lucky and Skillful Winner


If you were there you wouldn’t need an description. If you weren’t there, come next year!

Needless to say there was a very lucky winner.


Race Schedule


Monday Nov. 5

See the boats on display at the Truman Waterfront. Then just 4 blocks on Southard Street relax with a cold one at the Irish Oak Barrel.

Tuesday Nov. 6

Boats on display and testing from 12Noon to 5PM. Plenty of time in the evening for quaffing a cold one at the Irish Oak Barrel.

Wednesday Nov. 7

Ten o’clock for the first race, then 1230, 1330, and 1430 for the 2nd, 3rd, and 4th races. Come into the Irish Oak Barrel and share stories and photos of the day’s racing. 

Thursday Nov. 8

Boats on display and testing from 12Noon to 5PM. Plenty of time in the evening for quaffing a cold one at the Irish Oak Barrel.

Friday Nov. 9

 Ten o’clock for the first race, then 1230, 1330, and 1430 for the 2nd, 3rd, and 4th races. Come into the Irish Oak Barrel and share stories and photos of the day’s racing.  


You’ll have plenty of time before the Duval Street party at 7PM to relax and enjoy a Guinness. After the press of the crowd on Duval, come back to the Irish Oak Barrel to refresh. 

Saturday Nov. 10

Boats on display and testing from 12Noon to 5PM. Plenty of time in the evening for quaffing a cold one at the Irish Oak Barrel. 

Come watch Notre Dame beat Florida State. 

Wish the Marines Corps a happy 243rd Birthday!

Key West Firefighter Frankie Gutierrez

We lost a brave soul.

Recently Frankie succumbed to his illness.  He was very well known and will be missed.  We at the Irish Oak Barrel mourn his passing, send our condolences to this family and remind all who read this that there is a GoFundMe site set up to defray the huge costs of battling his disease.


Sunday Nov. 11 Final Race Day and Awards

Thanksgiving Week at the Irish Oak Barrel


Monday Night Football

Watch Monday Night Football and enjoy $5 Stella Artois brews

Tuesday Pre-Thanksgiving Specials

You know Thanksgiving is coming. You’ve seen all the Christmas sales that herald Thanksgiving. Let’s stay a bit tropical and enjoy $5 rum drinks.

Wednesday Pre-Thanksgiving “Dinner” party


Yes the Irish Oak Barrel is serving Thanksgiving “turkey dinner” in the Irish Oak Barrel tradition. Come get your free range, no artificial additive, lean, Wild Turkey shots for $5. 


 Yes we know that Thanksgiving is a day that we all appreciate our lives, health, family and good fortunes and gather with our family and friends. Many will stuff themselves with a stuffed turkey until the tryptophans kick in. We would like to thank our friends and customers that have helped bring this Irish Oak Barrel to Key West and who bring life to our pub. Thank you very much for your patronage. If you need a break from your Aunt Edna, we will be open from 4PM to 4AM Thanksgiving day to Black Friday morning. 

Friday “In the Biz Day”

We’re “in the biz” and you know if you’re in the biz. If you are then come into the Irish Oak Barrel for $5 well drinks of your choice. We’re all in this together.

This is it! The last Notre Dame Game. Time for a blow out tailgate party!

Notre Dame has had a great season! Let’s tailgate. We’ll be out front and in the courtyard Sponsors will be the Irish Oak Barrel, Salty Angler, and Jameson under the tents! Come dressed in Notre Dame colors, apparel or as a leprechaun and get a gift from the Irish Oak Barrel.

Notre Dame Schedule

Notre Dame flag will fly!

Notre Dame v Virgina Tech

Notre Dame wins 45  to  23

Notre Dame v Pittsburgh

Notre Dame wins against Pittsburgh 19 to 14.  Still undefeated!

Notre Dame v Navy and Fantasy Fest!

Notre Dame wins 44 to 22.  

Still undefeated!

Notre Dame v Northwestern

Notre Dame wins 31 - 21!

Notre Dame v Florida State

Notre Dame wins 31-21!

Notre Dame v Syracuse

Notre Dame wins in a near shutout.

Other Events


Thanksgiving Weekend

Notre Dame vs USC and a $5 turkey dinner (Wild Turkey bourbon)

November 17th Notre Dame v Syracuse

Come cheer on Notre Dame to undefeated Victory! Have some cheer while you’re at it!

Rob Benton Live at the Irish Oak Barrel

December 29th at the Super Tailgate Party

Rob Benton is one of the hottest Acoustic  performers out of New Hampshire.
Widely  acclaimed as one of the top acoustic guitarists in the United States.  Rob's unique, and innovative style of playing has lead to 3 albums  released, radio and film success and multiple tours performing to sold  out venues across the US & Canada

Rob's  style is extremely unique, and very entertaining to the eyes and years.  Lending Percussion, looping, beat boxing, and an electrified rock  element to his solo acoustic playing, which enables Rob to sound like a  3-4 piece band. His style is his own though hinted with a collection of  the sounds of those who have influenced him over the years.

Rob  has spent the better part of of 10 years performing alongside Lee.  Brice, Jerrod Neiman, Colt Ford, Candlebox, Skidrow, J. Geils Band, Gary  Hoey, Everlast and many others.

A little background....

In  2008, Rob teamed up with multi-platinum selling pop artist and Boston  neighbor, Rich Cronin (formerly of the boy band super group LFO) to  record the tracks which would become Rob's solo debut. ​
Rob signed a recording contract with Orange Freeze Records, and his album   "Dawn Meets Day" was released.

​In  early 2011, Rob began writing and recording demo tracks for a new  release which would be titled "Finding Me".  This record would be very  personal, and touch on several different subjects that have had major  impacts in Rob's life. ​
"Some good...some not so good".

In  2012, Rob was asked to join the band LANSDOWNE as their lead  guitarist.  A band which is currently touring nationally and playing  along side bands such as Nickleback, creed, Pop Evil, Theory Of A  Deadman, Eye Empire, Hell Yeah!, Tremonti, POD, Nonpoint and Taproot.

In  2013 Rob was offered a contract with The MGM Grand, and moved to Las  Vegas for a 1 year contract performing as a headliner at Circus Circus  Casino, on the Vegas strip.
The show ran 5 nights a week for the year, and was successful enough that he was approached by world
renown producer John Stuart, of Legends In Concert.
Rob was offered to take the lead role as Johnny Cash in this show.

Since  2014, Rob has signed a deal with the Fleury Group which secured him a  full time residency performing nightly shows at Bernie’s Beach Bar in   Hampton, NH & The Goat (country bar) in Portsmouth, NH.


Charlie is our favorite Scottish singer of Irish tunes

Lovable Charlie


Charlie's back from Ireland.  And he's ready for the girls

Scotsman Charlie RAGG plays Irish tunes


You remember the raucous great time we had the last time the Salty Craic played at the Irish Oak Barrel.   Charlie  Ragg ramps it up!

Charlie's been in Ireland soaking in the Irish tunes.


The tunes are better with Irish whiskey.

Rob Benton Played


 2007 winner RJL Memorial Battle Of The Bands

2008 winner WBCN Rockn Rumble

2008 contestant NBC's Americas Got Talent

2011 Rolling Stone- youtube watchers poll top 100 USA Acoustic Category

2012 New England Music Scene online vote - #1 Solo Act.

2014 Headline Entertainer for Las Vegas - Circus Circus Resort & Casino 

Rob Benton plays at the Irish Oak Barrel.

Chris Toler jammed with Charlie


Never before together at the Irish Oak Barrel!  A clash of music.

Sean Styles sang everything!


He sings! He plays the guitar upside down and backwards! He cranks up the crowd!  Sing with his band! He plays all the songs he knows and some of those he doesn't...

Jack Wolf plays at the Irish Oak Barrel


Key West's Own Jack Wolf Plays

Come hear Jack Wolf at the Irish Oak Barrel tonight starting at 8:30.

Most  of the great singer songwriters are difficult to put into a specific  category… as it is with Jack Wolf.  Is it Soulful?... Americana?...  Alternative?... Rock?... yes it is!  He  loves all music and no specific influence really stands out.  Some fans  hear a Jack Johnson or Kings of Leon sound… the essence of Van Morrison  is also prevalent.    

There is a definite blend of sounds that  have settled deep in his soul… the key to his strength both as a  vocalist and lyricist.    His self penned tunes show off his talent and  passion…. by the second listen you will find yourself singing along.

Robin Sunquiet - Familiar songs, Funky Tropical Originals


Robin Sunquiet singer, multi-instrumentalist, song writer, producer plays Thursday

Robin Sunquiet is an American  Multi-Instrumentalist, Singer-Songwriter, Producer, who combines the  funky uptempo dance party beats of modern DJs, with the raw energy of  live vocal and instrumental performance.  He is largely influenced by  Michael Jackson, Paul Simon, Ed Sheeran, Prince, and Michael Franti, as  well as DJ’s like David Guetta and Rudimental.  With a focus on diverse  world dance rhythms, simple catchy vocal choruses, and soulful guitar  riffs, he draws even the most tentative audiences onto the dance floor  to sing along.  He has appeared at iconic venues such as The Boulder  Theater and Higher Ground Ballroom, and has shared the stage with live  music festival road warriors such as Easy Star Allstars, Kung Fu, and  The Ready Set.  His 2017 release, “Elastic Love”, is available now on  Itunes and Spotify; it’s appropriately named—-Robin’s live show is an ELASTIC dance party brimming with LOVE that will make your sweat roll over your smile. 

Emerald Society Thursday

Emerald Society Discounts


Come to the Irish Oak Barrel on Thursday and receive 20% off on all purchases.  Enjoy the evening with other Emerald Society Members; all police, fire, EMT, and military.

Listen to Robin Sunquiet


Robin Sunquiet will play at the Irish Oak Barrel on Thursday Night; Emerald Society Night. Come enjoy a multitalented musician rocking the night.