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Start by eating a balanced diet, and then add foods from the oil and grain groups. Plant-based oils, like nuts, peanut butter, trail mix, olives, mayonnaise, and salad dressing are healthy and add extra calories quickly. Grains, such as bread, cereal, pasta, and baked goods, are tasty and easy to eat.  Eat more often than three times  a day and never skip a meal.  In between meals, and before bed, sip on high calorie beverages like juice, milk, and hot cocoa, and eat a small snack like dried fruit.  Visit About.com to learn more about how to gain weight.