St. Matthews By-The-Sea began in a tent in Fenwick Island in the summer of 1961 under the direction of the Rev. David Baker, then pastor of Salem Methodist Church in Selbyville. Three lots on Dagsboro Street and Highway 1 were purchased and construction began in June, 1962. A concrete floor was laid and services were held with the sky as the roof. Construction continued and the Cornerstone was laid in September, 1962. In the fall of 1963 two lots adjacent to the church were purchased to provide parking space. Additions and improvements continue at the church on a regular basis.

As Fenwick Island and the surrounding area grew and many people began to make this their permanent home, the decision was made to have a permanent congregation in Fenwick. On January 13, 1990, the Rev. Dr. Donald O. Clendaniel, Sr. was appointed pastor and served until 1999 when Rev. Bruce Miller became the pastor July 1, 1999.

Under the leadership of Rev. Miller many new ministry opportunities began here at St. Matthews.  It was then St. Matthews received its first Associate Pastor, Rich Evans.  Together, Rev. Miller and Rev. Rich Evans worked with the people of St. Matthews to establish the Samaritan Thrift Shop.  The Thrift Shop's success should be credited to Nancy Scheffey, its director for its first six years and to the current director Janice Slaysman, as well as all of the shop's many volunteers.  

Rev. Bruce Miller faithfully served at St. Matthews By-The-Sea for 20 years until June 30, 2019 when he retired. Rev. Mike Hurley was appointed Pastor on July 1, 2019, and served as our Pastor through the beginning of the Covid pandemic; Rev. Hurley retired on June 30, 2021. On July 1, 2021,  Rev. Jake Macklin began serving as the next pastor of our church. Our church is more than a building; it reaches out to the community and provides a welcome place of worship for visitors as well as our own members.