History of the 1st Squadron 299th Cavalry Regiment

Posted on Jan 13, 2025 in HING History, Units

The 299th Cavalry Regiment, formerly the 299th Infantry Regiment was established in August 1923 from the old 2nd Hawaiian Infantry Regiment, and serves as one of the core units of the Hawaii National Guard. The unit’s nickname as “The Hawaiian Guardians” demonstrated the role the unit would play in helping to protect Hawaii. The call sign “Koa” comes from the Hawaiian word for “Warrior”, linking the unit to its Hawaiian warrior past. The unit now consists of the 1st Squadron, 299th Cavalry Regiment, and is headquartered in Hilo with its attached Forward Support Company. The unit maintains one dismounted Troop on Kauai and two mounted Troops on Oahu. Initially an Infantry unit, the unit was reflagged as a Cavalry Regiment in 2007.

During the 1920s and 1930s, the 299th Infantry Regiment underwent numerous changes in formations and locations throughout the islands. In 1935, the 299th Infantry Regiment had reorganized again moving it’s Regimental Headquarters from Hilo to Honolulu, the unit positioned the 1st Battalion on Maui and the 2nd Battalion on the island of Hawaii. There were plans to recruit and maintain a 3rd Battalion, which would bring the Regiment to full strength. During this time the 299th Infantry continued to recruit from many of the plantations workers on Maui and Hawaii Island and conduct their weekly drills to improve their warfighting capabilities. They continued Officer and Non Commission Officer professionalization as they received Active Duty Officers to coach and mentor full time on the Islands of Maui and Hawaii. As the 1930s closed out, the 299th Infantry Regiment continued to train for a possible war in the Pacific, while balancing the peacetime mission of support to the Territory of Hawaii with disaster relief and civil support. During the Great Depression, funding issues and selective demographic recruitment hampered readiness until the end of the 1930s.

By early 1940, the 299th Infantry Regiment was a key part of the US Army’s defense of Hawaii, rounding out the newly established 24th Infantry Division as one of their Infantry Regiments. With the possible expansion of World War II spreading to the United States, the National Guard, to include the 299th infantry Regiment was federalized activated in October 1940 and President Roosevelt authorized the Selective Training and Service Act authorizing a peacetime draft. To defend “the Gibraltar of the Pacific”, the draft expanded the pool from which to recruit from bringing many races previously not allowed to serve to be drafted in higher number. New recruits were brought into the unit and the Regiment was brought to full strength and trained at Schofield Barracks. Hawaii prepared for a wartime footing and by May 1941, the 299th Infantry Regiment was sent to the neighbor islands to build defenses and prepare for a possible war in the Pacific.

Following the Attack on Pearl Harbor December 7th 1941, Martial Law was declared in the territory and the 299th Infantry Regiment were already defending Hawaii with positions on the Islands of Hawaii, Maui, and Kauai. The Battalion Commanders were essentially the Military Mayors for each of the counties reporting to the US Army’s Military Governor on Oahu.  Under Martial Law, the 299th Regiment was responsible for many facets of live, directing everything from blackout drills, public rationing, war bond drives, to supervising the Police. On January 28, 1942, the Regiment lost 17 Soldiers as they returned to Hawaii Island after completing basic training at Schofield Barracks when their ship was sunk by a Japanese submarine crossing the channel between the Islands of Hawaii and Maui.  Only nine Soldiers survived and were taken to Hana, Maui.  The Soldiers and the town of Hana were sworn to secrecy, families didn’t find out how their loved ones died to the end of the war. Soldiers who were Americans of Japanese Ancestry remained with the unit May 1942, when nearly half of the Regiment was transferred to the Hawaiian Provisional Battalion and shipped to the Mainland for training. This unit would soon become the 100th Infantry Battalion, which left the Regiment severely understrength and it was deactivated in July 1942. For its service, the Regiment was awarded Campaign Credit for the Central Pacific. Parts of the unit was activated as the 532nd Field Artillery Battalion and participated in the Western Pacific, Philippines, and Ryuku campaigns. For its service some units of the 299th Infantry were awarded the Philippine Presidential Unit Citation.

The 299th Infantry Regiment was reactivated in October 1946 as the 299th Regimental Combat Team. The unit continued to train and provide support across the state during times of crisis as America transitioned into the Cold War. In 1963, the unit was reorganized with the 1st, 2nd, and 3rd Battalions, 299th Infantry Regiment, becoming elements of the newly formed 29th Infantry Brigade. In 1968 the 1st and 2nd Battalions, 299th Infantry Regiment, were activated during the Vietnam War and served at Schofield Barracks, while also providing replacements to active duty units in country, in Vietnam.

In 1995, only the 2nd Battalion, 299th Infantry Regiment remained as an element of the 29th Infantry Brigade, while the 1st and 3rd Battalions were deactivated. The unit continued to support the State for disaster relief such as hurricanes, civil disturbances, and volcanic activity. In 1999, the 2nd Battalion, 299th Infantry Regiment also participated in a challenging Joint Readiness Training Center rotation. The unit maintained a presence on the Islands of Hawaii, Maui, Molokai, Oahu, and Kauai.

Following the attacks of September 11, 2001, portions of the 2nd Battalion, 299th Infantry Regiment were activated across the state providing security in the early 2000s. In 2004, the 2nd Battalion, 299th Infantry Regiment was activated and federalized and began a six month train up to deploy to Iraq. In 2005 the Battalion was deployed to Baghdad and was based out of Camp Victory in Baghdad where it was charged with base defense. In addition, the Battalion was also responsible for security in the areas and neighborhoods surrounding Camp Victory and conducting patrols and cordon and search missions to capture, kill, or disrupt the enemy insurgents in the area. During the deployment the battalion’s strength was augmented by the attachment of A Company, 2nd Battalion, 297th Infantry Regiment from the Alaska Army National Guard. The battalion redeployed from Iraq in February 2006. For its service, 2nd Battalion, 299th Infantry Regiment was awarded the Meritorious Unit Citation as well as with an Iraq Campaign Streamer.

In 2007, the 2nd Battalion, 299th Infantry Regiment was reflagged and became the 1st Squadron, 299th Cavalry Regiment. The unit focused its mission on providing reconnaissance and security, transitioning away from its prior Infantry role. The Squadron maintained units on the Islands of Hawaii, Oahu, and Kauai. In 2008, the unit was again federalized and activated to serve as convoy escorts for convoys traveling from Kuwait into Iraq. As “TF KOA”, the Squadron deployed with the Headquarters, Troop A, and Troop B. They further deployed with Company A, 29th Brigade Special Troops Battalion, and Battery A, 1st Battalion, 487th Field Artillery. The Squadron logged over 10,000 miles and engaged in numerous contacts with the enemy. During this time the unit provided many individual Soldiers who deployed to Afghanistan and the Philippines in support of Operation Enduring Freedom. The unit was again awarded its second Meritorious Unit Citation for its service and Iraq Campaign Streamer.

In 2018, the Squadron was federalized, activated, and deployed as Peacekeepers to the Sinai, Egypt as part of the Multinational Force and Observers (MFO) mission. Rather than wearing the United Nations’ blue beret and helmet cover, the MFO is an independent peacekeeping organization. Here the 1-299th Cavalry Soldiers, now known by their rotation number United States Battalion 65 (USBATT65), wore the orange beret, caps, and helmet covers to symbolize their roles as Peacekeepers in a Multinational Peacekeeping Organization. The Squadron served with and within Combined Joint Battalions and Staff from October 2018 through July 2019.

Throughout the 299th Infantry and Cavalry Regiment’s lifecycle, it has proudly served in National Guard Civil Support missions. The missions the unit has participated have gone beyond hurricane and volcano support. These missions have ranged from swift water rescue during flooding, to security support for large scale events, wildfire support, to providing support for the COVID-19 pandemic. In every emergency that has faced the State of Hawaii, and when the nation has called up its members for active service, the 299th Cavalry Regiment and it’s lineage of the 299th Infantry Regiment has answered the call.

Last updated Jan 2025

Lineage And Honors Information

(HAWAIIAN GUARDIANS)

  • Constituted and partially organized 27 January 1893 in the Hawaii National Guard as the 1st Regiment
  • Organization completed 1893-1895 with Headquarters at Honolulu
  • Redesignated 1 June 1907 as the 1st Infantry
  • Drafted into Federal service 1 June 1918 as the 1st Hawaiian Infantry
  • Demobilized 7 July-2 August 1919 at Fort Shafter, Territory of Hawaii
  • Reconstituted 1 October 1919 in the Hawaii National Guard; concurrently consolidated with the 5th Hawaiian Infantry (partially organized in the fall of 1918 as a Home Guard Regiment) and consolidated unit designated as the 1st Infantry
  • Redesignated 17 August 1923 as the 298th Infantry; Headquarters Federally recognized 26 June 1924 at Honolulu
  • Inducted into Federal service 15 October 1940 at Honolulu
  • Assigned 1 October 1941 to the 25th Infantry Division
  • Relieved 23 July 1942 from assignment to the 25th Infantry Division and assigned to the 24th Infantry Division
  • Relieved 12 June 1943 from assignment to the 24th Infantry Division
  • Regiment (less 1st Battalion) inactivated 10 April 1945 at Schofield Barracks, Territory of Hawaii (1st Battalion inactivated 22 January 1946 at Schofield Barracks, Territory of Hawaii)
  • Reorganized and Federally recognized 14 October 1946 with Headquarters at Honolulu
  • Heavy Mortar Company, Medical Company, and Companies, B, D, G, and L converted and redesignated 7 January 1957 as the 298th Antiaircraft Artillery Battalion (remainder of 298th Infantry – hereafter separate lineage)
  • Consolidated 15 February 1959 with the 299th Infantry (see ANNEX 1) and the 487th Field Artillery Battalion (see ANNEX 2) and consolidated unit designated as the 299th Infantry, a parent regiment under the Combat Arms Regimental System, to consist of the 1st and 2nd Battle Groups, elements of the 29th Infantry Brigade
  • Reorganized 1 April 1963 to consist of the 1st, 2nd, and 3rd Battalions, elements of the 29th Infantry Brigade
  • Reorganized 15 November 1965 to consist of the 1st and 2d Battalions, elements of the 29th Infantry Brigade
  • (1st and 2d Battalions ordered into active Federal service 13 May 1968 at home stations; released 12 December 1969 from active Federal service and reverted to state control)
  • Withdrawn 1 May 1989 from the Combat Arms Regimental System and reorganized under the United States Army Regimental System
  • Reorganized 1 October 1995 to consist of the 2nd Battalion, an element of the 29th Infantry Brigade
  • Ordered into active Federal service 16 August 2004 at home stations; released from active Federal service 11 February 2006 and reverted to state control
  • Redesignated 1 October 2005 as the 299th Infantry Regiment
  • Converted and redesignated 1 September 2007 as the 299th Cavalry Regiment, to consist of the 1st Squadron, an element of the 29th Infantry Brigade Combat Team
  • Ordered into active Federal service 19 August 2008 at home stations; released from active Federal service 22 September 2009 and reverted to state control

ANNEX 1

  • Constituted in the summer of 1915 in the Hawaii National Guard as the 2nd Infantry
  • Organized and Federally recognized 12 October 1915 with Headquarters in Hilo
  • Consolidated 1 July 1917 with the 3rd Infantry, the 4th Infantry, and the 1st Separate Company of Infantry (all organized 1915-1916 in the Hawaii National Guard) and consolidated unit designated as the 2nd Infantry
  • Drafted into Federal service 1 June 1918 as the 2d Hawaiian Infantry
  • Demobilized 14 February 1919 at Schofield Barracks, Territory of Hawaii
  • Reconstituted 29 June 1921 in the Hawaii National Guard as the 2nd Infantry
  • Redesignated 17 August 1923 as the 299th Infantry; Headquarters Federally recognized 1 January 1927 at Hilo
  • (Location of Headquarters changed 28 February 1934 to Honolulu)
  • Inducted into Federal service 15 October 1940 at home stations
  • Assigned 1 October 1941 to the 24th Infantry Division
  • Inactivated 21 July 1942 in Hawaii and relieved from assignment to the 24th Infantry Division
  • Reorganized and Federally recognized 8 October 1946 with Headquarters at Hilo

ANNEX 2

  • Constituted 19 May 1944 in the Army of the United States as the 532nd Field Artillery Battalion
  • Activated 31 May 1944 at Schofield Barracks, Territory of Hawaii
  • Inactivated 23 December 1945 at Seattle Port of Embarkation, Washington
  • Redesignated 4 August 1946 as the 487th Field Artillery Battalion and allotted to the Hawaii National Guard
  • Organized and Federally recognized 5 May 1947 with Headquarters at Hilo

CAMPAIGN PARTICIPATION CREDIT

World War II

  • Central Pacific
  • Western Pacific
  • Leyte
  • Ryukyus

War on Terrorism

Iraq:

  • Iraqi Governance
  • National Resolution

DECORATIONS

  • Meritorious Unit Commendation (Army), Streamer embroidered IRAQ 2005-2006
  • Philippine Presidential Unit Citation, Streamer embroidered 17 OCTOBER 1944 TO 4 JULY 1945

Last updated Apr 2014