Leah Boss guides the spirit of reggae to the region

Leah Boss (photo by Dion Ogust)

When Leah Boss was in her 20s, living in New York City, she marched with Malcolm X and Martin Luther King, Jr., and she was an organizer with the Students for a Democratic Society (SDS). “The soundtrack of that liberation time,” as she calls it, included reggae, with Bob Marley and others singing for justice and freedom.

After moving to Woodstock at the age of 27, she began booking reggae musicians to perform in the Hudson Valley. Her next event is a Love Boat Cruise on Sunday, September 1, when the boat Rip Van Winkle will board passengers at 5:30 p.m. at Kingston’s Rondout for a trip down the Hudson, with Jamaican food and a deejay spinning reggae music. The last show of the season will be a concert by the Grammy-winning band Arrested Development at The Chance in Poughkeepsie on Saturday, September 14, at 8 p.m.

“I came to Woodstock for peace, nature, and culture,” said Boss, “the same things that move me about reggae. The music is about respecting nature, and it calls for peace, love, and freedom. There wasn’t any reggae around here when I moved up, and I couldn’t live without it. I was already involved in the reggae scene in the city before moving to Woodstock in the 70s. So, like a good Woodstocker, I proceeded to make it happen.”


Over the years, Boss has organized over 300 shows, featuring about 200 bands at more than 150 venues, including colleges, outdoor festivals, the Bearsville Theater, Joyous Lake, UPAC, and many others. Having worked as a teacher, she said, “I felt for it to sink in, I would have to bring it often, not just once a year. And I had to book a variety of different styles and bands, so it was always fresh.”

She brought Jimmy Cliff to Opus 40, drawing the biggest turnout the outdoor rock sculpture amphitheater had ever seen. Other well-known performers have included the Wailers, Ziggy Marley, Burning Spear, Third World, Steel Pulse. “I’ve worked with many legends and many up-and-coming artists, who are kind of like my children,” she said. “Now bands like The Big Takeover are touring the country.”

Before reggae took over her life, Boss taught English language enrichment at Onteora High School, Kingston High School, and the Woodstock Children’s Center, which is now the Woodstock Day School. “It’s satisfying to see young people I taught many years ago coming to my shows,” she said. “Reggae is intergenerational. At a show, I see young people all the way up to senior citizens. One woman brought her 87-year-old mother. It was the first time her mother had danced in decades.”

The September 1 cruise will offer passengers an opportunity to hear the history of reggae music. The deejay will also take requests on the evening ride along the river, ranging as far south as Poughkeepsie. The historic boat can accommodate 300 people, so be sure to make a reservation, and arrive at least an hour early, as Kingston’s Hooley on the Hudson Irish Festival will slow your progress toward the dock.

The Chance, where Arrested Development will perform, is a landmark music venue. The band, said Boss, “plays everything from rhythm and blues to gospel to soul to reggae. They played at the 1994 Woodstock Festival in Saugerties. They’re a family band, which means a lot to me because reggae and Woodstock, to me, means family. The lead singer does poetry to music, speaking about peace, love, freedom, and taking care of the earth.” The opening band, DisNDat, performed last year at the Colony, and their drummer formerly played with the Jamaican group Black Uhuru.

Boss hopes people will take inspiration from reggae to protect both nature and culture. Referring to the Lion of Judah, a symbol of reggae and the Rastafari movement, she said, “The lion leads the way to help us stand strong.”

The Reggae Love Boat Cruise boards at the Strand in Kingston, on Sunday, September 1, at 5:30 p.m. To make reservations, contact Leah Boss at (845) 657-4047. The cost is $35 per person and includes a Jamaican meal. Parking is available at Kingston Point Beach or at the Hannaford’s near the Trailways station, with shuttle buses to the Rondout. Allow at least an hour to get from parking to the dock.

Arrested Development will perform at The Chance, 6 Crannell Street in Poughkeepsie, on Saturday, September 14, at 8 p.m. Tickets are $50 to $70. Make reservations through The Chance box office at (866) 777-8932 or https://www.thechancetheater.com.