Values associated with statewide freight and tourist mobility; traffic, pedestrian, and bicycle safety; and small-town livability create competing objectives that are difficult to balance when main streets of small towns are also state highways. Many communities opt for bypass solutions to these issues, but the Philomath Couplet Project represents a main street solution that is sensitive to both the demands of the state highway system and the character of the local community. The controversial 10-month decision process culminated in the selection of a preferred alternative. Final design is under way, and construction is scheduled for 2006. Although many projects are developed according to context-sensitive solution principles, the Philomath Couplet Project represents a class of projects with characteristics likely to be faced throughout the United States in relation to the management of state highways that are also main streets of small towns. The difficulties encountered in conducting this project provide important insights to guide context-sensitive solutions implementation in these circumstances. The lessons learned shared in this paper highlight the need to manage the "end game" of small-town politics, the value of time and cost constraints, the need for a structured decision process, and the usefulness of evaluation criteria based on interactions of land use and transportation.