Bob McCaffrey (1943-2025)

Robert “Bumpy” McCaffrey Jr. was born on March 27, 1943, at Butterfield Hospital to the late Robert and Mary (Landolfi) McCaffrey. He was a lifelong, third-generation Cold Spring resident. Robert passed away peacefully on Jan. 2, 2025, at NYP Hudson Valley Hospital. He was 81.

Growing up in Cold Spring, Bumpy spent many years at McCaffrey’s, a bar and restaurant owned and operated by his parents at the intersection of 9D and Main Street in the village.

He graduated from Haldane in 1960 and went on to pursue a teaching career at Monmouth University. Bob taught business classes at Lakeland High School for over 20 years before a friend suggested that he obtain his real license. Little did Bob know, this would lead to another long and successful career of entrepreneurship at the well-known Robert A. McCaffrey Realty. Over the years, many of his clients became dear friends to Bob.

Some may not know that Bumpy was an avid philanthropist who contributed to many local charities and organizations that were near to his heart. He served on numerous boards which reflected his profound love for the arts, local history and his church.

Throughout his life, he enjoyed travel, dancing, fine dining, spending time with family and friends and never went out before dressing in his finest attire. In his retirement, he enjoyed sitting on the front porch of his Main Street residence where he would strike up friendly conversations with neighbors. Those who were fortunate enough to know him would often hear him say, “Don’t get old, stay young and wonderful!”

Bumpy is survived by many beloved family members and a host of dear friends that will cherish his memory.

Bob will be waked on Monday, Jan. 6, 2025, from 4 to 8 p.m. at Clinton Funeral Home, 21 Parrott St., Cold Spring. A Mass of Christian Burial will be celebrated on Tuesday, Jan. 7, 2025, at 10 a.m. at Our Lady of Loretto Church, 24 Fair St., Cold Spring. Interment will follow in Cold Spring Cemetery.