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  • Writer's pictureEileen Markland

Hilltop Treasure

In 2008, my family realized dreams of pine scented breezes, woodland creatures coming to visit, snow shoeing by light of a full moon and spectacular star lit skies. Indeed, it was love at first sight when we found our paradise in Windsor, just past the Peru town line.

I was THRILLED to learn that Windsor is actually home to a number of artists and musicians. I had the pleasure of meeting one such hilltop treasure, Samantha Talora, about 20 miles away from Windsor on a warm summer day in 2013. We were both hired, she to sing and I to play the violin, for a concert in Lenox. For me, it was love at first glorious sound. She is remarkably talented, with a crystal clear soprano voice and a gift for story telling. What a joy to discover that she is also an immensely sharp and beautiful human being!

I recently had breakfast with Samantha at her home, where she and her husband have been living for 10 years. Sam and Nick, like my family, moved from Cheshire after finding the home and land they’d always dreamed of in Windsor. We enjoyed delicious fruit, pancakes and a beautiful view of the winter woods while discussing her winding and scenic path to today.

Sam has been singing as long as she can remember and was a member of her church choir as soon as she was old enough to join. It became apparent that St. Mary’s had an especially gifted young singer and she was soon being asked to sing solos. With a laugh, Sam describes falling in love with the microphone and wondering, “Where else can I do this?” She sang in talent shows and her first professional “gig” was singing at a wedding at 12 years old. She continued to be active throughout middle and high school, participating in the school chorus, musical theatre productions and Western District and All State choruses.

In her senior year of high school, Sam had to choose a path. Her parents offered two different perspectives. Her mother, “always practical”, wanted her to pursue a course of study that would assure employment with steady income and a stable lifestyle. Her father, “more of an artistic type”, thought she should pursue a career in music performance. Sam describes her choice of the Arts Administration Degree Program at Wagner College in Staten Island, NY as her way of honoring the sage advice of both parents.

At Wagner, Sam sang every day and “found her community”. Dr. Roger Wesby, Director of Choral Activities and Vocal Studies, introduced her to different styles of music. Sam particularly enjoyed her participation in his elite vocal ensemble called “Stretto”, a co-ed 8 person a Capella performing group with tight harmonies. She also participated in Wagner’s Theater Department, Opera Workshop and College Choir, in addition to her studies in business and liberal arts.

Just after the start of her senior year, September 11, 2001 happened. She was on Staten Island, across the New York Harbor, overlooking the NY skyline. One of the beautiful memories she has of that time is of singing at the many memorial & remembrances ceremonies and seeing, firsthand, how the music brought healing to the community.

Sometime during her sophomore year, Sam began dating Nick, a high school friend. Both returned to the Berkshires after college graduation, got married and Sam again faced major life choices: Stay in the Berkshires or go back to the city? Chase auditions and a career in performance or focus on family? The newlyweds chose to build their home in the Berkshires.

In 2004 Sam really began to feel pressure to “get a grown up job” and stopped seeing music performance as her path. She did not sing at all again until 2010, and during this period she completely immersed herself in hospitality and event planning. She began with a position in the sales office at Cranwell, which morphed into an event-planning role at the resort. Sam soon launched her own successful event planning business and also worked for the Town of Adams and Canyon Ranch during these years.

The music never really left her, though, and without music Sam didn’t feel complete. She describes her return to singing in 2011 as part of a healing process during a very difficult time. “There was a lot of loss and change in my life at this point. Music found me, came back to me when I really needed it. “ For the next three years, Sam gradually returned to performing by singing in weddings, at churches and in local theatre productions and fundraisers.

On the same day in 2013 that I met Sam at the concert in Lenox, we both met Berkshire native Ron Ramsay, a career singer, pianist and music director who had recently left a Broadway career in New York City to be close to his family. A collaboration between the two vocalists soon followed and, inspired by their shared love of decades of Broadway music, the Great American Songbook, classic standards and contemporary & popular music, the two have been weaving beautiful harmonies ever since. They soon brought in Michael Gillespie, a talented wind specialist and music educator who is Director of Bands for the Berkshire Hills Regional School District. I am also a frequent guest violinist in their shows, which boast a loyal Berkshire following and are still going strong after five years.

Sam treasures her friendship and professional relationship with Ron: “We have had a fantastic five years together. Not only is he a tremendous musician, singer and pianist, he’s been an invaluable mentor and dear friend to me.”

What is most striking about Sam, beyond her kindness and obvious talent, is her deep reverence for her craft. Her greatest musical influences span from Miss Piggy to Frank Sinatra to Eva Cassidy to Pavarotti, from Country to Broadway to Opera to Gospel. Her favorite songs are those that tell a story, familiar songs that touch her audiences deeply and personally. She loves to sing at known venues as well as brand new venues where the unexpected can and always does happen! She loves the telling of the story. “The process of developing a theme for a show, finding the right songs, analyzing the meaning of each song by dissecting the music and lyrics until I deeply understand the story, and sharing that story with an audience, brings me great satisfaction.”

Samantha admits that it’s not easy to juggle a full time “day job”, personal life AND a busy performance schedule. How does she manage it all? “I don’t sleep a lot and I have a very patient and understanding husband. Balance is always a challenge.”

She continues, with smiling eyes, “Music has never failed me. It’s always here for healing. Music has pulled me off the ledge more than once. I am just filled with gratitude. Bottom line is that I love it and I’m never going to stop.”

Learn more about Samantha Talora and her upcoming performances at:, follow her at and

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