One Of Connecticut's Most Expensive Vacation Destinations Is A Town Tucked Inside A Mid-Century Wonderland
At first it might seem odd that in the middle of the last century, some of the world's most cutting-edge architects all lived and worked in the sleepy suburban Connecticut town of New Canaan. But it makes more sense when you realize that some were European and had left post-World War II Europe behind, and that the East Coast -– home to many of the universities where they studied and taught –- was the first place they'd land in the U.S. Perhaps most importantly, New Canaan is just over an hour's drive from Midtown Manhattan.
New Canaan is part of the Gold Coast of Connecticut, so named for the wealth that is reflected in grand estates, hedge funds, and pastimes like polo and sailing. It's surrounded by other affluent enclaves like bougie and beautiful Darien and Greenwich with its chic restaurants and beaches. With a population of just over 20,000, New Canaan is a small community where the cost of living is nearly 39% higher than the U.S. average, according to Build magazine, and the average home value is $1.975 million, according to March 2025 estimates from Zillow. Visitors will notice higher-than-average prices for gas, hotels, and meals. However, there's value in what the town has to offer: a picturesque downtown, art galleries and cultural centers, pretty parks, and both preserved Colonial and mid-century modern architecture.
A car is needed to get around New Canaan, but if you're coming only for the famed Philip Johnson Glass House, Metro-North Railroad has a stop across the street from the visitor center where shuttles to the house depart.
New Canaan features mid-century modern buildings
There are 91 verified examples of mid-century modern houses in New Canaan still standing, the most famous being the Philip Johnson Glass House. Operated by the National Trust, the house is open for tours May-November. The property has 14 buildings, including an art gallery and a guest house, on 49 acres. Even if you don't do the tour, peruse the museum store in the visitor center downtown. Johnson built the house for himself in 1949 and lived there until his death in 2005. He was one of the "Harvard Five" — a group of architects associated with the Harvard Graduate School of Design and influenced by Bauhaus founder Walter Gropius who built homes for themselves and others in New Canaan beginning in the 1940s. The other four architects were Marcel Breuer, Landis Gores, John M. Johansen, and Eliot Noyes. The style is known for simplicity, minimalism, functionality, open floor plans, and integration with nature.
The New Canaan Museum & Historical Society is the best local resource to learn about and tour the non-Glass House homes. The museum has a collection of books, films, and photos about the homes and the movement and presents exhibitions and lectures. It also organizes the biannual Modern House Day Tour; the next one is October 17-18, 2025. October is a great month for mid-century modern fans to come to New Canaan for the museum's 10-day October4design festival that includes tours, classes, and talks about architecture, art, and design.
What else is there to do in New Canaan?
Architecture fans will want to walk through the acclaimed "River" building at Grace Farms, an 80-acre cultural center and nature preserve. The award-winning building, designed by SANAA, undulates like a river and uses glass to blend with its environment. Waveny Park is a 450-acre park with walking trails, sports fields, gardens, and the Carriage Barn Arts Center, which hosts art exhibitions and events. This artistic community also has the Silvermine Arts Center, which holds classes and exhibitions. Also check out the 40-acre New Canaan Nature Center, a sanctuary with trails, gardens, and programming for children and adults.
Downtown New Canaan features both national retailers like J. Crew and locally owned stores, art galleries, and restaurants such as the well-reviewed Pesca Peruvian Bistro (its lomo saltado gets high praise from diners) and the pan-Asian Ching's Table. The historic movie theater downtown recently had life breathed into it: The Playhouse of New Canaan now offers not just films but also live events as well as a pub and lounge. Not far from downtown, the New Canaan Library has robust programming including author talks and educational programs. Stay overnight at the historic Roger Sherman Inn with 17 guest rooms priced beginning in the $300 range. Dating to 1740, the inn is an elegant property with a destination French-American restaurant where you can order escargots, duck a l'orange, and steak frites. New Canaan doesn't have a beach, but only about an hour's drive away is the beach town of Old Saybrook, known for its scenic views, rich history, and antique shops.