This research examines the site and situation characteristics of community trails as landscapes promoting physical activity. Trail segment and neighborhood characteristics for six trails in urban, suburban, and exurban towns in northeastern Massachusetts were assessed from primary Global Positioning System (GPS) data and from secondary Census and land use data integrated in a geographic information system (GIS). Correlations between neighborhood street and housing density, land use mix, and sociodemographic characteristics and trail segment characteristics and amenities measure the degree to which trail segment attributes are associated with the surrounding neighborhood characteristics.