Tripp was born and raised in Harrisonburg, the fifth generation of Dentons still living in Harrisonburg! Tripp's great grandfather, Jefferson Simon (J.S.) Denton, started a furniture business in 1878; in 1921 he moved the furniture business to downtown Harrisonburg. Denton's was a downtown destination until 1992! The Dentons closed the furniture store to pursue commercial real estate and a communication business.
The real estate business is still going strong for Denton Downtown Properties with Tamarack Townhomes, the Hostetter Building which includes 12 offices on the second floor and 2,700 square feet of retail space where the Oasis Fine Art & Craft Gallery currently resides. The Hirsch Building has two upscale apartments on the second floor; a popular burger joint operates on the ground floor, Cuban Burger.
Tripp worked with his father in the communication business since 1987; he started Intouch Communications in 1996, offering paging services, two way radio service and tower management. Presently, Intouch Communications supplies the Denton Center with internet service.
Tripp is a member of the Harrisonburg Rockingham Chamber Commerce and the Downtown Renaissance.
Denton's Furniture on Court Square in downtown Harrisonburg, circa 1921. The Denton Center was renovated in 1996 to includes retail space on ground floor and 44 apartments on upper levels.