An hour out of Manhattan, this town in prosperous Fairfield County has one of the highest median family incomes in the United States.
New Canaan wields real artistic and architectural clout: The feted sculptor Solon Borglum settled here in the early 20th century, and the prestigious Silvermine Arts Center is a product of the colony he founded.
The Harvard Five, a gang of early Modernist architects, made a lasting impact on New Canaan’s residential townscape in the 1940s and 50s, building homes with open floor plans and using innovative materials.
One of the Five, Philip Johnson designed himself the visionary Glass House, which opens for tours and is not to be missed.
1. The Philip Johnson Glass House
Philip Johnson (1906-2005) built himself this Modernist dwelling as a weekend retreat in 1949. As the name tells you, the Glass House has transparent glass walls, and these are on a symmetrical steel structure.
The only completely private element is the brick-lined bathroom.
Johnson was a follower of Ludwig Mies van der Rohe, helping the Bauhaus director to come to America during the Nazi regime, and the Glass House was influenced by Mies van der Rohe’s Farnsworth House (1947) in Plano, Illinois.
Johnson visited the property for 58 years with his long-time partner David Whitney, who passed away in the same year and helped design the grounds, and collected most of the art on show.
There’s a choice of tours, starting and ending at the Visitor Center in Downtown New Canaan, the most concise lasting for an hour and the most in-depth taking place on weekends and lasting for 2.5 hours.
2. Waveny Park
One of the founders of Texaco, Lewis Lapham commissioned this stately Elizabethan-style mansion, known as “The Castle” in 1912. Waveny House is in 300 acres of flowing grounds laid out by Frederick Law Olmsted, Jr., and would stay in the family until 1967 when it was sold to New Canaan to become this distinguished park.
As well as being a grand place to take a wander, Waveny Park has its fair share of amenities, including an Olympic-size open air-pool and paddle tennis courts.
It’s also prominent in New Canaan’s events calendar, staging weekly concerts on Wednesdays in summer, as well as the Fourth of July fireworks, plays at the Powerhouse and an annual Easter egg hunt.
The house needs a mention for its mullioned windows and turreted chimney stacks, and was designed by William Tubby.
3. Silvermine Arts Center
A point of reference for Fairfield County’s vigorous arts scene, the Silvermine Art Center is an art school and exhibition space with five galleries.
New Canaan’s Silvermine community has art in its veins, going back to 1908 when the sculptor Solon Borglum relocated here and established a little colony.
The Silvermine Guild of Artists was founded in 1922, and the school followed a couple of years later and now schedules more than 100 courses each year.
Exhibitions here are accompanied by symposia and panel discussions, and there’s an exciting program of lectures and visits by artists, as well as outreach workshops at schools in the area.
HeART & Mind, a landmark exhibition in late 2019, was matched with programs addressing mental health issues and the healing power of art.
4. Grace Farms
Completely open to the public, Grace Farms is a non-profit center dedicated to initiatives concerning nature, the arts, community, justice and faith.
The main edifice here, called The River, is worth the visit alone: Completed in 2015, it was designed by the Pritzker Prize-winning Japanese architecture firm SANAA.
Radiating a sense of peace, this long, sinuous structure is made from glass and concrete, with a Douglas fir canopy supported by steel pillars.
This houses a 700-seater amphitheater, a tea pavilion, a library, a commons space with an excellent organic cafe and a sunken court for performing arts and recreation.
Grace Farms is in 77 acres of immaculate grounds, navigated by walking trails, around the site you can seek out contemporary art installations by the likes of Teresita Fernández, Olafur Eliasson and Thomas Demand.
5. New Canaan Historical Society
Documenting the town’s past, the New Canaan Historical Society (founded 1889) owns or operates eight museums and historic buildings, most of which are located at the society’s campus on Oenoke Ridge.
Of all the society’s properties, only the Little Red School House and the Gores Pavilion (more below) are off campus.
At the main location you can check out exhibitions expertly curated from the society’s massive collections, and get a taste of life in New Canaan in days gone by at the Rock Schoolhouse (1799), Cody Drug Store (1845), the Town House (1825), the Hanford-Silliman House (c. 1764), the Rogers Sculpture Studio (1878) and the Tool Museum and Printing Office.
The main exhibit in summer 2019 was “Shoes”, with 200 pairs helping to map out the shoemaking industry in New Canaan, which flourished for more than a century.
6. New Canaan Nature Center
There’s 40 acres of restorative landscaped and untended greenery at the New Canaan Nature Center, containing an arboretum, botanical garden and nature preserve.
The landscaped spaces include a marvellous wildflower garden, in which 90% of the species are native, along with a herb garden and a perennial border growing hepatica, Jacob’s ladder, crested iris and bleeding heart.
There’s a 370-square-meter greenhouse to check out, while out in the natural areas you can explore two ponds, an historic orchard, wet and dry meadows, cattail marsh and wet and dry woodland.
Finally the arboretum has a small but admirable collection counting Swiss stone pine, weeping Norway spruce and moss sawara cypress.
7. Carriage Barn Arts Center
A 19th-century stone barn in Waveny Park houses this not-for-profit gallery and performing arts venue.
The Carriage Barn Arts Center showcases local and regional talent, putting on eight high-profile exhibitions each year, four of which are juried and four featuring members and invited artists.
All exhibitions are open to the public and free, although there’s a suggested donation.
Check the website for the center’s rich array of programs, including workshops in watercolours, collage and gouache led by professional artists.
8. Mead Memorial Park
A town park brimming with amenities, Mead Memorial Park is set just off Park Street.
For sports you’ve got lighted and unlighted baseball fields, batting cages, tennis courts and an open-air skating rink under lights in winter.
The playground is unusually big, and has a separate fenced area for littler children.
If you’re here to relax you’ll find picnic areas, a pond and the recently opened Lodge at Mead Park, serving breakfast, lunch and dinner, and with a lovely terrace looking over the fields.
9. Browne Wildlife Sanctuary
The New Canaan Land Trust owns a handful of sanctuaries and trails around the town, including this remote 10 acre parcel of woodland with picturesque vistas of the Grupes Reservoir to the west.
Along the short but sweet trail there are interpretive boards with facts about the geology, ecology and the various human uses for the site over time.
Here and there you’ll come across some sizeable glacial erratic boulders.
10. Summer Theatre of New Canaan
Now relocated to Downtown New Canaan, this open-air tent theatre sets up during in June and July, presenting a professionally produced program of shows for audiences of all ages.
During this brief season there are short runs of mostly Broadway shows, as well as child-oriented entertainment and one-night-only performances, all for audiences of around 200. These productions call on fresh local talent both on stage and behind the scenes, working alongside professional performers and production staff.
11. Irwin Park
The newest park in New Canaan is at the junction of Wahackme Road and Weed Street, in 36 green acres if you need a dose of chlorophyll.
Irwin Park has come through improvements in the last couple of year and has newly laid down walking/jogging trails, threading through open grassy fields, past interesting sculpture and imposing mature trees.
A good time to be here is early spring, when the daffodils are a delight.
The eye-catching Modernist building at Irwin Park is Gores Pavilion (1960), designed by Landis Gores, a member of the Harvard Five, as a pool house for John Irwin and Jane Watson, who was the daughter of the founder of IBM.
The building is maintained by the New Canaan Historical Society and opens to the public in the afternoon from Friday to Sunday between May and November.
12. Mill Pond Park
On sunny days in summer this park next to Route 123 is a good choice for picnics or to lose yourself in a book for an hour or two.
On the pond’s banks are paths with benches under the cover of tall pines and hardwood trees.
The pond is the scene for an annual fishing derby for kids in spring, and in winter becomes the best place to go ice skating in New Canaan when the lights come on.
This activity is dependent on the weather of course, and signs on the banks will let you know when the ice is safe.
13. St Mark’s Episcopal Church
The current St Mark’s was constructed on the northern edge of New Canaan in the late-1950s, and embedded in its Modernist design are nods to neo-Gothic architecture.
Accompanied by a separate bell tower, the church can seat 600 and has lots of exquisite details, from the vibrant stained glass on three sides to the free-standing altar and floor-to-ceiling reredos adorned with bronze sculpture by Clark Fitzgerald.
Every element was designed purposely for this building.
St Mark’s is on leafy grounds and becomes the center of attention in New Canaan for the May Fair, featuring rides, games, entertainment, delicious food (strawberry short cake of course) and the huge May Fair White Elephant Tag Sale.
14. Stamford Museum & Nature Center
A few minutes west on the Merritt Parkway in the woods of North Stamford is a museum combining art, nature, agriculture and history.
The Stamford Museum & Nature Center is on a former private estate in 118 acres, ten of which are home to the working Hecksher Farm.
The galleries in the half-timbered Tudor Revival museum building are wonderfully eclectic, from paintings by John Singer Sargent, Warhol and Dalí to Native American artifacts, telescopes, vintage local pedal cars, keys and locks by Stamford’s famous Yale brand and farming implements.
Also here are important collections by Stamford-related artists like Gutzon Borglum (famed for Mount Rushmore) and Reuben Nakian.
On Hecksher Farm you’ll find heritage livestock breeds, as well as more exotic animals like burros, llamas and alpacas.
15. New Canaan Halloween Parade
On the Sunday before Halloween is one of New Canaan’s most anticipated events, and one with kids at the heart of the fun.
Wee ones, their parents and even their dogs dress up in all manner of wacky and spooky outfits and set off down Elm Street.
Leading the parade is the shiny Old Faithful, a 1924 LaFrance fire truck.
There are goodie bags for kids, as well as lots of entertainment and live music.
Grandparents and local residents line the street to cheer the parade on.