Advances in the field of material engineering, computerization, automation, and equipment miniaturization enable modernization of the existing technologies and development of new solutions for construction, inspection, and renovation of underground pipelines. Underground pipe installations are used in the energy sector, gas industry, telecommunications, water and sewage transport, heating, chemical industry, and environmental engineering. In order to build new pipeline networks, dig and no-dig techniques are used. Horizontal Directional Drilling (HDD) is one of the most popular trenchless technologies. The effectiveness of HDD technology application is mostly determined by its properly designed trajectory. Drilling failures and complications, which often accompany the application of the HDD technology, result from poor design of the well path in relation to the existing geological and drilling conditions. The article presented two concepts of Horizontal Directional Drilling well path trajectory design: Classic sectional, which is a combination of straight and curvilinear sections, and a single-section chain curve trajectory (catenary). Taking into account the advantages and disadvantages of the catenary trajectory relative to the sectional trajectory, the author’s solution was presented, which was the implementation of the sectional trajectory with a maximum shape similarity to the catenary trajectory. The new approach allowed us to take advantage of a chain curve trajectory and was easier to implement using the available technology. The least squares method, based on deviations from a catenary trajectory, was set as the matching criterion. The process of searching for a trajectory, being a combination of straight and curvilinear sections as similar as possible to a catenary-type trajectory, was carried out using two methodologies: State space search and a genetic algorithm. The article shows the pros and cons of both optimization methodologies. Taking into account the technical and technological limitations of HDD drilling devices, a new approach was proposed, combining the methodology of state space search with the genetic algorithm. A calculation example showed the application of the proposed methodology in an engineering design process.