Right-of-way acquisition is a substantial element of the cost of many highway construction and expansion projects. Given land price appreciation on the one hand and the opportunity cost of owning land on the other, a great deal of money can be at stake in the question of whether right-of-way should be purchased well in advance of when construction is expected to take place. This paper develops a theoretical framework for thinking about this issue and describes some results from an analysis at a fairly aggregate geographic level. The general result is that early acquisition is not a good investment in the most general sense, given the average rate of land price increase and the cost of money as well as other costs associated with early acquisition. The one clear exception is land that is in imminent danger of development. A major limitation of this work is that it viewed land prices only in the aggregate and did not specifically examine the immediate vicinity of the right-of-way. The research did find some support for the notion that certain types of land in specific locations can appreciate in price much faster than the average. It is not clear, however, that it is possible to predict these situations with sufficient accuracy to take advantage of the potential cost savings.