Keys, Counterculture, and an American Hippie
Rich “In Spirit” McKay – Keys, Counterculture, and an American Hippie
Rich and a group of Key West musicians performed at the No Kings Rally.
Rich McKay grew up in City Island in the Bronx in New York City. His family discouraged music study but Rich and his brother insisted. He graduated from Mount Saint Michael’s High School in 1962.
Rich leading the Crooks Second Line March.
McKay started playing guitar while attending Marist College in the small town of Poughkeepsie, New York. He sang harmonies with a college band, the Frobisher Bay Volunteers. They entered competitions with other college groups, like Colgate, and never lost. After graduation, he taught school, teaching history, geography, and social studies. His teaching career was very short.
He smoked pot, tripped a few times (LSD), and later opened a head shop in Poughkeepsie. He was a card-carrying member of the 60s counterculture, attending Woodstock in 1969, as well as the 30th Woodstock Anniversary. Naturally, he was drawn to the 70s Key West counterculture vibe, and discovered he could do what he loved – play music in the warm American Caribbean. The Survivors and Pacific Orchestra were the big bands in 1977 Key West when Rich arrived. 
McKay began as a camper in a 16-member commune near the Navy base on Rockland Key, making a little money performing at Mallory Square and living the good life in 1978. His first friend in Key West was artist Tony Gregory. Another friend, current restauranteur Bobby Mongelli who was also staying in the commune, taught him how to collect conch on low tide.
He quickly joined Gary Zimmerman’s Solaris Hill String Band, playing music on Mallory Square, and also performed on the Western Union sunset cruises. He wrote music and recorded with John Krauss, captain of the Western Union, who kept his recording equipment in the back of the Western Union office. McKay wrote “Tale of the Western Union” and an autobiographical song “American Hippie”.
Rich and his group perform at the 2023 Key West Musicians Festival.
The former Orchid Tree Restaurant was home of weekend jams with the Survivors and a duo with Rich and Elaine Silver. A favorite hangout, The Rooftop Café restaurant was the 80s-dance place. Later, Rich helped form the band, Grand Ole Osprey, that performed at the Green Parrot with Bo Dobbs, Karen “Ooo La La” Grant and “Bounce” Margil.
In 1984, he watched Captain Finbar sail into the harbor aboard Schooner Wolf. Rich quickly made a deal and began performing 3-4 times a week on sunset cruises routinely for a gig that stretched the next 29 years (2013).
The Rainbow Gathering, billed as a meeting of all the Hippie tribes, started shortly after Woodstock, usually in July somewhere in the mountains all over the country and then expanded internationally. Rich began attending in 1990 with local friends who owned the Sugar Apple whole foods. While attending, most people select a “rainbow name”. He chose Rich “In Spirit” and has been attending and participating ever since.
Shel Silverstein was always walking around town and was very open with McKay. They spoke often, becoming very good friends. Shel loved to collaborate with anyone he found interesting and he made several offers to Rich. While walking along Duval street one day near today’s Fogarty’s, Silverstein stopped and asked if McKay wanted to hear a new song he had just written. He began playing Rich’s guitar and a large crowd gathered. The crowd increased as Shel played a second tune and the police disbursed the group for blocking the sidewalk. Today, Rich always regrets never collaborating with Shel on songwriting projects.
Rich and the Sun Dogs perform at the 2024 Key West Musicians Festival.
The Sun Dogs was a duet formed in the 90s with Art Descoteaux who played violin, vibraphone, and guitar. They played together for over a decade, performing at the Porter House on the corner of Duval & Caroline. McKay recently revived the Sun Dogs as a quintet with Gerry Theis on bass, Paulie Walterson on drums, Nancy Beck on dobro, and Art Descoteaux on fiddle. Some of the players leave for the summer and they plan to resume again during the season.
McKay recorded three albums: Learning to Love (1999) which was recorded live at the Pier House, To Make This World One of Love (2007), and While I’m 64 (2009). Most musicians enjoy performing with Rich because it’s never been about the money. 
RB Tolar calls Rich the real deal. As irony would have it, Rich McKay currently drives for Uber & Lyft, and when he plays an original song on the car stereo, like “Montserrat” or “All About the Ball”, his customers love it. He gets great tips and sells more CDs now than when performing the songs.
Rich “In Spirit” McKay has recorded over 50 songs. His most autobiographical recording, “American Hippie” was recorded with Art Descoteaux, Chief Billy, Din Allen, Woody Allen, and Quint Lange. When asked why he has stayed in Key West all these years, Rich responded, “The music and friends, and maybe the weather” are the most important things that keep Rich in Spirit in Key West.
The amazing life of a Keys Hippie.
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