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Meet the Performers: Summer in the City

Published on June 4, 2024


As we set sail for what is shaping up to be a sensational summer in Boston, we are excited to start talking about some of the talent we have the privilege of hosting this summer! Whether your taste is whiskey and country classics, or ice-cold beer and the blues, Summer in the City surely has a night planned for you. Read more about some of our featured performers below.

Explore The Lineup

    • Photo of the stage where 5 band members are playing. Text across the top left reads

    World Premier Band: June 11th, July 10th, and August 7th

    World Premier Band consists of five talented individuals, each with their own unique story. Tony "SweetP" Hobbs is a seasoned drummer and vocalist, with over 30 years of experience and a background from Berklee College of Music. He has played in many Boston nightclubs and for thousands in Hyannis, MA. Luke "Spice" Jackson is known for his high-energy performances and has toured the Bahamas, Florida, and the East Coast. As a soloist, he continues to shine with his original songs and studio work in New England.

    Jerron "Jiggy" Oliver, or “The Jiggy Man,” grew up in Boston and is passionate about dancing, rapping, and singing. He has opened for big acts and was nominated for “Best New Hip Hop Group” at the Boston Music Awards. CC “Biggs” Cabral, a Berklee College of Music alum, drives the band’s groove with his bass lines. He has played with bands like The Energetics and Hypertension. Lastly, Cory “Sugar Bear” Waldron is a versatile musician with a background in classical voice and jazz guitar, contributing to the band’s rich sound.

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    • Black and white photo of Rich DiMare who is holding a microphone and singing

    Rich DiMare: June 12th, July 24th, and August 21st

    Rich DiMare, an acclaimed American jazz singer, is celebrated for his masterful interpretations of the Frank Sinatra songbook. Known across the country, his unique Sinatra experience blends humor and charm, bringing to life classics like "My Way" and "New York, New York." With more than two decades in the entertainment industry, Rich has honed his craft as a performer. His talents extend beyond singing, as he also DJs at Fenway Park, the beloved home of the Boston Red Sox. Rich's voice was a staple on Kiss 108, Boston’s top-rated radio station, where he spent 15 years on-air, and he has also hosted live TV segments on Boston’s Fox25.

    On tour, Rich is joined by Ron Poster & The Sinatra Ambassadors. Ron Poster, the longtime organist for the Boston Bruins, brings over 20 years of experience to their performances. The collaboration between Rich and Ron on stage, combined with their deep knowledge of the Sinatra repertoire, creates a captivating experience for audiences. Their shows are a homage to Old Blue Eyes, delivering a nostalgic and entertaining performance that Rat Pack fans will not forget. Each concert is a celebration of Sinatra’s timeless music, performed with a flair that keeps the magic of the era alive.

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    • Live Music on the Harborwalk Terrace being played for a lively audience

    Shana Stack Country Band: June 14th, July 25th, and August 9th

    Step into the vibrant world of New England’s country music scene with the Shana Stack Band, a leading force renowned for their dynamic performances and compelling original music. Having graced the main stages alongside country legends such as Toby Keith, Craig Morgan, Travis Tritt, and The Marshall Tucker Band, this band knows how to captivate an audience. Shana Stack Band's impressive resume includes opening for top-tier acts like Luke Bryan, Lady Antebellum, Brad Paisley, and Reba McEntire at the prestigious Bank of NH Pavilion. Their talent has also shone brightly on stages across New England, from the Comix Roadhouse at Mohegan Sun Casino to the historic Colonial Theater and the bustling New Hampshire Motor Speedway. With four albums under their belt, including hits like "You Can't Make Me Fall" and "What You See Is What You Get," the Shana Stack Band delivers a mix of heartfelt ballads and toe-tapping anthems. Their music, available on platforms such as iTunes, Amazon, Spotify, and YouTube, resonates with fans old and new. For a taste of authentic country charm with a New England twist, the Shana Stack Band is your go-to choice.

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    • Black and White Photograph of Steve Memmolo in a suit

    Steve Memmolo: June 20th and August 1st

    Steve Memmolo is a multi-talented musician who has captivated audiences with his versatile vocal abilities and dynamic stage presence. Growing up surrounded by the timeless tunes of the Great American Songbook, Steve has become one of Boston's premier "Rat Pack" style singers. His influences range from the smooth sounds of Frank Sinatra to the soulful stylings of Donny Hathaway and Bobby Caldwell, creating a unique blend that appeals to music lovers of all ages.

    A finalist on Season 15 of NBC's The Voice, Steve's journey on the show as part of Team Adam displayed his remarkable talent and connected him with a nationwide audience. Beyond his success on television, Steve owns and runs Classic Yellow, a Boston-based party band that delivers unforgettable performances at weddings and corporate events. His dedication to entertainment does not stop at music; he also brings joy to audiences with his weekly improv comedy performances. Steve's musical releases, including his singles "Upside Down" and "Cruel with Love," highlight his exceptional songwriting and vocal prowess. Available on platforms like YouTube, his music offers a soulful escape that leaves listeners wanting more.

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    • Musician Amanda Stewart playing the guitar on stage in front of a band.

    Amanda Stewart: July 12th

    Amanda Stewart’s journey in the entertainment industry began on a ranch in Bozeman, Montana. Amanda’s roots were influential in carving out her niche in the music industry; Stewart’s sound is best described as a culmination between Americana, Folk, Country, and Pop. With over 15 years of performing across the country, we welcome her to Summer in the City and cannot wait to have her sound here on the harbor! Amanda's recent releases reflect her dynamic range and heartfelt lyrics. Her single "Me or the Whiskey" dropped on March 22nd, 2024, followed by "Better Be Good" set to release on June 7th, 2024. Fans can look forward to even more new music from Amanda this summer as she continues to rise in the country music world.

    Amanda Stewart has made waves in the country music scene, earning recognition and praise from several esteemed publications. Her talent has been spotlighted in Cowgirl Magazine, Holler Country, DittyTV, The Bluegrass Situation, The Boot, and Americana Highways. Amanda's captivating performances have also landed her on the popular show "Today in Nashville" for a performance spotlight, showcasing her musical abilities to a wider audience. In 2024, Amanda's songwriting skills were acknowledged as she became a finalist for the prestigious Rocky Mountain Songwriter Contest. Her growing reputation has seen her share the stage with notable artists such as Tyler Childers, Jordan Davis, Jennifer Nettles (of Sugarland), Clint Black, Ned LeDoux, Chancey Williams, Brett Dennen, and Craig Morgan.

    Photo Credit: Erin Crowley