Our season opens with The Drifters on Friday, June 15th!
The Kennebunks' newest entertainment venue
The finest in national, regional, and local music talent throughout the summer and fall season.
Vinegar Hill Music Theatre
Now in our third season, this live music venue offers the finest in national, regional, and local music talent throughout the summer and fall. A gracious, historic barn, Vinegar Hill is an intimate venue that provides entertainers with a superlative, vibrant setting to showcase their talents. Featuring a variety of genres, like cabaret, classical, rock, folk, and blues, Vinegar Hill Music Theatre resides in the former Arundel Barn Playhouse, a timber barn known as the Smith Sister’s Farm. Located in an area of Kennebunkport’s Arundel, historically known as Vinegar Hill, the venue’s name honors that history.
When attending one of our performances, arrive early to enjoy the charming outdoor garden area and one of our signature classic cocktails from the rustic Garden Bar. Social seating and twinkling globe lights create a relaxing setting and help set the tone for an evening of incredible entertainment.
About Vinegar Hill
Tim Harrington and Debbie Lennon, Managing Partners
Tim Harrington, managing partner for Vinegar Hill and the Kennebunkport Resort Collection, acquired the Arundel Barn Playhouse from Adrienne Grant, the founder of the playhouse, upon her retirement in 2016. A longtime fan of the playhouse, Tim wanted to continue the tradition of offering live entertainment in Arundel and the Kennebunks and had long admired the historic barn setting. Moving in a direction of live music rather than plays, Tim hopes to celebrate the local and regional talent in the area, along with bringing some national acts to the barn. Tim is passionate about integrating the music theater into the fabric of the community, offering opportunities for children’s theater and not-for-profits to utilize the space.
Operating and business partner, Debbie Lennon, joins Tim in his vision for the theatre and the benefit it can bring to the area. Her background in hospitality and operations enables Debbie to manage the day-to-day happenings, as well as the feet on the ground team who makes the magic happen onsite. A music lover, Debbie is dedicated to creating an experience that’s appealing to guests and entertainers alike, ensuring a robust calendar filled with top notch talent.
Sarah Dearing, Managing Director
Sarah Dearing was a California native, with family roots that moved her to Maine in the early 1990’s. She quickly fell in love with it and started a family and career, raising her two children here. Her work in the entertainment industry started during childhood, where she performed in countless school plays. After high school, she realized she preferred managing performances behind the scenes rather than being on stage, and has since made her mark “behind the curtain” in New England for the past twenty years.
In 1997, she was introduced to her first live comedy show, which lead to a twenty-year adventure; managing and booking acts at the Comedy Connection, Maine’s only full time stand-up comedy club. In addition to that work, she became Production and Merchandising Manager of the quickly growing Bob Marley Comedy Tour. The Bob Marley Tour brought Sarah back to her favorite place and moment – standing on an empty stage, staring out into the empty house and preparing for the flurry of activity that comes with producing the next sold out show.
In 2000, with the beginning of the infamous Bob Marley Holiday Shows at Merrill Auditorium, Sarah added stage design to her repertoire, bringing Bob and his team’s visions to life. As the show grew so did the sets, crews, and stage management. By 2003, the team had transitioned from releasing their self-produced CDs, to shooting hour-long comedy specials in small theaters and clubs along Bob’s tour. Over the years, Sarah assisted with management and production of several comedy DVDs, TV shows, and Webisodes; as well as a full coverage documentary on Bob Marley’s epic, 40 hour, Guinness Record Breaking set that raised $22,000 for the Barbara Bush Children’s Hospital. She also worked with a team from Sony Pictures on the premiere of Boondock Saints II.
In 2012, Sarah launched a consulting business, Spotlight Solutions, Inc., where she continues to grow her corporate, non-profit entertainment planning and merchant services capabilities. Among them, she has been bringing comedian Juston McKinney to theaters across Maine, continues to manage booking and ticketing for several Portland venues, and manages a book of 150 corporate clients.
She is the perfect addition to the Vinegar Hill team in that she has broad experience in both front and back of the house roles. Her extensive operational experience, industry know-how and connections, and genuine love of theater and entertainment will enable Vinegar Hill to bring incredible acts to our stage, providing an unforgettable experience for guests.