Howie moved to New York City in 1968. He initially lived at the famous Hotel Albert, and began to form relationships with New York musicians. Howie had a book of all the talented musicians in the city. To make it into the famous “black book” was a great achievement. He used this book whenever someone would call looking for instrumentalists and vocalists. Howie heard people play, put their names in his “black book”, and recommended them for jobs, sometimes without even meeting them; he had heard them, and knew they could play.
Howie was best known for being the drummer (and occasional pianist) for Bob Dylan on both the Rolling Thunder Revue in 1974 & 1975, and the Desire album. The Rolling Thunder Revue was an informal, constantly changing all-star tour that included Joan Baez, Joni Mitchell and others. He rehearsed for the 1978 tour, but withdrew before the tour began. He rarely toured after that.
Howie continued his musical career in New York City. He was comfortable playing jazz, soul, rock, folk, and country styles, making him difficult to categorize. He played with jazzman James Moody, soul singers Zulema and Don Covay, rockabilly revivalists Robert Gordon & Link Wray, folk artists James Hardy, Christine Lavin, and Richard Meyer, Richard Shindell, and at many of the "Fast Folk" concerts. He played on Blues Traveler's debut album that won a RIAA Gold record award, selling more than five hundred thousand copies. He also played with Jono Manson, pop artist Don McLean, and bassist Rob Stoner. He also played in the legendary New York City group, The Worms. He recorded two albums with Nice Boys from New York.
Later in his career, he decided to concentrate on piano, and led many of his own groups playing ragtime, blues, zydeco, and early jazz at many New York clubs. He recorded an album of Ragtime and Stride piano called "Chadd's Ford Getaway".
Howard married Rona Morrow in New York City. They eventually divorced. Howie had a special relationship with his partner of 17 years, Catherine Wheeler. She was instrumental in bringing out the best in Howie, and he loved her. Breaks Howie’s band took during a performance quickly became “Catherine breaks”, as he called her many times during each working evening. It’s how he could play such a grueling schedule, sometimes playing seven nights a week.