Juneteenth’s New Birth of Freedom

Christopher Holshek
3 min readJun 21, 2021


On Saturday, 19 June 2021, local American Legion Riders, National Service Ride, and Hudson Valley Veterans Task Force and especially Buffalo Soldiers Motorcycle Club riders led the first Juneteenth Underground Railroad Freedom Ride through Orange County, NY.

To commemorate the new national holiday, the nearly 40 riders started at Port Jervis, the entry point for the Underground Railroad into New York on the Delaware & Hudson Canal and later the Erie Railroad for fugitive slaves seeking freedom in the North and Canada. Before the rail line, most came over a network of turnpikes and other roads, finding refuge in homes along the way, including the Henry Green Homestead in Florida, NY. After picking up more riders in Newburgh, they rode into Highland Falls, next to the U.S. Military Academy, to join the town’s parade and celebration.

Signed into federal law last Thursday, Juneteenth commemorates the end of slavery in the United States on 19 June 1865, when Gen. Gordon Granger announced to the last group of enslaved African Americans in the South, in Galveston, TX, that the Civil War had ended and they were free persons. This came more than two years after President Abraham Lincoln issued the Emancipation Proclamation on New Year’s Day, 1863.

Juneteenth, however, is about more than the end of slavery. It is also about the beginning of freedom, which is at the essence of American identity. Many who led the Ride were veterans of the armed forces, police, and other national and public services.

We should not forget that our military is not the most fearsome fighting force in the world because of its awesome firepower and technology. It is in its embodiment of our national values in our original motto — e pluribus unum. It is, in fact, the single largest, most successful multicultural institution in history, united in the defense of the cause of freedom.

Our veterans have come from every walk of life and corner of our society. Some — like 2nd Lieutenant Emily Perez, who was the highest-ranking African-American female cadet at West Point, enshrined at the nearby American Legion Post 1573 in Harriman, NY — have given their last full measure of devotion to that cause.

And if our military can come together in affirmation of that cause, so can the rest of us in its confirmation. As Americans, we should honor their example by giving them a country worth our sacrifices.

Now as then, we need to rise above our differences and work together in the service of our communities as well as our country. The value of service above as well as for self is a unifying as well as democratizing force for an embittered and divided society nearing irreconcilable dysfunction.

In many ways, as a moment of reconciliation, Juneteenth represents what Lincoln called at Gettysburg “a new birth of freedom” to form that more perfect union — now, as then, a moment of opportunity in a time of great national and societal peril.

Freedom is a long, hard, and never-ending road — for all of us, and not just some. For, if only some Americans are fully free, then none of us are.

But freedom also entails the responsibilities of citizenship we must take up to guarantee the rights that we claim, closing the gap between our ideal and our reality. That comes from us more than our leadership.

Juneteenth is another reminder of our calling to face the challenges of our time, then pass the baton in continuation of that same struggle for freedom to the next generation — moving, like motorcycles, inexorably forward, together as well as on our own.

Holshek, Colonel, U.S. Army Civil Affairs (Ret.), is a member of the American Legion, founder of the National Service Ride project, Senior Civil-Military Fellow at the Alliance for Peacebuilding, and author of Travels with Harley — Journeys in Search of Personal and National Identity.



Christopher Holshek

Christopher Holshek, Colonel, U.S. Army (Ret.) is author of Travels with Harley — Journeys in Search of Personal and National Identity