Trip Ideas

Great Estates

There’s always been a certain romance in touring grand properties and imagining them as your own. Take this trip through western Connecticut, for instance, and you’ll drop in on the former estates of an industrialist, an architect, a painter and an heiress. You’ll see just how good life can be – or was.

1-2 days

  • Spring
  • Summer
  • Fall

  • Lockwood-Mathews Mansion
  • The Glass House
  • Artist’s Estate
  • Out into the Country
Lockwood-Mathews Mansion Museum (c.1864) - Reopens for tours in Spring 2025, Norwalk

Lockwood-Mathews Mansion

Begin in the afternoon here at the stunning Lockwood-Mathews Mansion Museum in Norwalk, regarded as one of the earliest and most significant Second Empire Style country houses in the United States. Built between 1864 and 1868 by financier and railroad baron LeGrand Lockwood, the Gilded Age mansion offers jaw-dropping interiors and architectural flourishes.

The Glass House, New Canaan

The Glass House

Philip Johnson’s Glass House in New Canaan, one of the most famous private residences in America, was completed in 1949. With its exterior glass walls and no interior walls it was a radical departure from most architecture at the time, and it remains so today. Be sure to tour the grounds and Johnson’s many outbuildings.

* Editor's Picks
Weir Farm National Historic Site, Wilton

Artist’s Estate

The morning brings breakfast at the inn and then a short ride to Wilton and the Weir Farm National Historic Site. The 60-acre estate was home to three generations of artists, including Julian Alden Weir, a leading figure in American Impressionism. In winter you can walk the grounds past his former home, studio, barns, gardens and Weir Pond.

Topsmead State Forest, Litchfield

Out into the Country

Next, it’s time to leave Fairfield County for the wilds (not really) of Litchfield County, where Edith Chase’s summer estate, now known as Topsmead State Forest, beckons. Chase’s English Tudor cottage is the focal point, but her grounds spread out in all directions, encompassing more than 500 acres in all. It's great for a brisk winter hike.

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