Opening Act

As a solo artist, Isaiah has opened up for several touring artists such as Frankie Ballard, Love & Theft and Brandon Lay over the years. He has a way with the audience and is known as a crowd-pleaser. Isaiah is always eager to play his originals and has enough material to play a set anywhere from 30 minutes to 3 hours. He is willing and loves to travel.


Isaiah performs for the ceremony and cocktail hour and then transitions into an award winning DJ/MC for the remainder of the evening, keeping the party going strong! He’s been featured in Maine Magazine, Brides Magazine, The Knot and is a five-time Couples Choice Award Winner from WeddingWire.

Visit the Weddings Page for more wedding package details.

Private Party

Having a party, function or gathering? Isaiah Bennett can help make your event one of a kind! He can sing any genre of music you request and can be background music or bring life to the party. He can play anywhere from a 2 to 5 hour set, has all of his own sound equipment and can provide microphones for speeches if needed.

Do you love to explore the Greater Portland area and it’s surroundings? Chances are you’ve heard Isaiah at some of Southern Maine’s hotspots. He plays at the Porthole Restaurant, Gritty’s, Allagash Brewery, The Brunswick, Dockside Restaurant, 33 Elmwood, Top of the East, Erik’s Church, Bonfire Country Bar and The Goat, to name a few. Notching in over 200 bar gigs each year, Isaiah is a young but seasoned musician who will entertain your guests with cover songs ranging from every genre and era.

Restaurant/ Bar