These are exciting days for cartography, as emerging technologies have greatly expanded the possibilities of online, interactive maps. These developments, however, now require cartographers to think about issues that only a few years ago fell solely in the domains of human-computer interaction (HCI) and web design. Further, given how fast these changes have occurred, there are few tried-and-true guidelines for building digital maps. This paper reports on the design, development, and evaluation of the University of Wisconsin-Madison Lakeshore Nature Preserve Interactive Map (www.lakeshorepreserve.wisc.edu) and outlines many of the insights gleaned from this process. The purpose of this article is to strengthen the important bridge between cartography and usability evaluation (i.e., how we study the way in which users interact with their maps and how we measure the success of those interactions) so that the efforts of a team of developers and stakeholders can be coordinated in a way that ensures the map works equally well for all potential end users. We outline the relative merits of two broad categories of evaluation techniques, arguing that there is no single, correct evaluation technique appropriate for all evaluation scenarios, and then detail the specific strategy adopted for evaluation of the Lakeshore Nature Preserve Interactive Map. We conclude by offering four design guidelines for online, interactive maps revealed during the evaluation of the Lakeshore Nature Preserve Interactive Map: two positive strategies we recommend for consideration when designing map interfaces (inclusion of cascading interface complexity and provision of map browsing flexibility) and two pitfalls we caution to avoid (minimalist design of interface widgets and employment of a lorem ipsum map during development).