Gardens and Grounds

With gardens, walking trails, and even a historic farm, Hill-Stead’s 152-acre historic landscape invites visitors to gather, explore, find inspiration, or simply linger to take in nature’s sights and sounds.

Enjoy a drones-eye view of Hill-Stead! with this video courtesy of Lev Verbitsky

Hill-Stead’s Gardens

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Photo by Deborah Key.

From the Sunken Garden to the rustic and now overgrown Walking Garden, Theodate Pope Riddle’s gardens were an important feature of the original Hill-Stead landscape and provided an outdoor space for the family to gather. The gardens remain a place to gather and continue to be essential to life at Hill-Stead, offering seasonal beauty, a home for butterflies, birds, and other creatures, and a spot for quiet contemplation.

Hill-Stead’s latest garden, the innovative Pollinator Garden, provides shelter and food to support pollinators. Native plants attract a variety of birds, butterflies, and other wildlife, providing diverse habitats and food sources.


Walking Trails

From apple blossoms to grand vistas and fiery fall foliage, Hill-Stead’s three miles of trails are exquisite in any season. With a pond habitat, meadows, lowland, lowbush, and forests, the trails are a nature enthusiast and bird watcher’s paradise.

Photo by Deborah Key.

Photo by Deborah Key.

Hill-Stead’s trails represent the rich historical legacy of the estate. Originating, most likely, with Native American walking paths, the trails encompass 18th- and 19th-century farmstead lands. Early 20th-century carriages and sleighs coursed through the grounds, later joined by mechanized farm vehicles and flocks of herded sheep. The trails have been enjoyed by such guests as Eleanor Roosevelt and Jacqueline Kennedy Onassis during her days as a Miss Porter’s School student in the late 1940s.

Today the trails are walked by neighbors and visitors from around the world. Children and families can enjoy a leisurely stroll and visit the sheep at Clatterridge Farm. Hikers looking for strenuous exercise can explore the Blue-Blazed Metacomet Trail, which runs along the eastern ridgeline of the estate. stroll.

About Hill-Stead’s Walking Trails

The trails are maintained through the generous efforts of faithful volunteers. If you would like to join this dedicated group of volunteers, visit our Volunteer page.


First Sunday Estate Walk

Held at 2 p.m. the first Sunday of each month, May through October.