Food shopping decisions are pathways between food environment, diet and health outcomes, including chronic diseases such as diabetes and obesity. The choices of where to shop and what to buy are interrelated, though a better understanding of this dynamic is needed. The U.S. Department of Agriculture's nationally representative Food Acquisitions and Purchase Survey food-at-home dataset was joined with other databases of retailer characteristics and Healthy Eating Index-2010 (HEI) of purchases. We used linear regression models with general estimating equations to assess relationships between trip, store, and shopper characteristics with trip HEI scores. We examined HEI component scores for conventional supermarkets and discount/limited assortment retailers with descriptive statistics. Overall, 4962 shoppers made 11,472 shopping trips over one-week periods, 2012-2013. Trips to conventional supermarkets were the most common (53.6%), followed by supercenters (18.6%). Compared to conventional supermarkets, purchases at natural/gourmet stores had significantly higher HEI scores (β = 6.48, 95% CI = [4.45, 8.51], while those from "other" retailers (including corner and convenience stores) were significantly lower (-3.89, [-5.87, -1.92]). Older participants (versus younger) and women (versus men) made significantly healthier purchases (1.19, [0.29, 2.10]). Shoppers with less than some college education made significantly less-healthy purchases, versus shoppers with more education, as did households participating in SNAP, versus those with incomes above 185% of the Federal Poverty Level. Individual, trip, and store characteristics influenced the healthfulness of foods purchased. Interventions to encourage healthy purchasing should reflect these dynamics in terms of how, where, and for whom they are implemented., (Copyright © 2018 Elsevier Inc. All rights reserved.)