The Allée and border gardens bring a combination of panoramic formality and small-scale intimacy to the landscape of the Oldfields estate. The Allée, a sweeping lawn lined with 58 red oak trees, stretches 775 feet in front of Lilly House, terminating with a circular pool and fountain. Designed by Percival Gallagher of the famous landscape architecture firm Olmsted Brothers, the Allée is a design element of stately grandeur—one that has been borrowed by American landscape architects from great European palaces and estates.

On either side of the Oldfields Allée, Gallagher added border gardens. These sun-and-shade gardens offer intimate spaces with changing views of flowers. Perfect for a relaxing stroll, these informal areas are often referred to as "the gardener's gardens," as they feature many interesting and unusual combinations of bulbs, perennials, annuals, shrubs and trees.

• Jack-in-the-pulpit, including stands of these spring-blooming natives and rare specimens of exotic Asian varieties
• Toad lily, a fall-blooming perennial growing up to 3 feet, featuring purple and white orchidlike flowers
• Hellebores, spring bloomers that carpet the border gardens by the hundreds, featuring white, green, purple, and striated flowers, and glossy dark green leaves that last into winter
• Oak-leaved hydrangea, a summer-blooming shrub for sun or shade with white flowers that fade to pink
• Copper beech, a relatively rare tree. The border gardens feature eight magnificent specimens that are approximately 80 years old
• A great variety of ferns, which add a lush feeling and contrast beautifully with larger-leaved plants like hostas
• Acanthus, a summer bloomer with dramatic, finely cut, dark green leaves
• Hardy begonia, a relative of the house plant of the same name, which covers itself in drooping pink blooms in fall
• Spring wildflowers, including Virginia bluebells, trillium, celandine poppy, and more
• Cut-leaved lilac, a shrub with profuse lavender flowers that perfumes the gardens in May