15 Best Things to Do in New Canaan (CT)

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. Typically they built 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. This is not to be missed and will kick off my article.

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. 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. I was fascinated to discover that he 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 of these lasts for an hour, while the most in-depth takes place on weekends and lasts 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. At that time 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. You’ve also got the Fourth of July fireworks, plays at the Powerhouse, and an annual Easter egg hunt.

I should also mention the beautiful house at the heart of the property. Designed by William Tubby, this has mullioned windows and turreted chimney stacks.

3. Downtown New Canaan

For me one of the very best things about New Canaan is its walkable and welcoming center. In quaint brick storefronts there’s an upscale choice of restaurants, cafes, galleries, shops, and other service businesses.

Browsing the shops you’ll come across wine, athletic gear, fashion, fabrics, jewelry, lighting, kitchen supplies, shoes, and much more. As well as independent boutiques, you’ve got locations for the likes of Ralph Lauren and Ann Taylor.

Things are just as eclectic when it comes to dining. On my last visit there was Italian, bagels, Mexican, breakfast food, patisserie, ice cream, New American, Peruvian, vegan fare—the list goes on.

A busy event calendar brings year-round bustle to these tree-lined streets. Take the dog-friendly block party at Halloween, or the village fair and sidewalk sale in summer.

4. 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. There’s also an exciting program of lectures and visits by artists, as well as outreach workshops at schools in the area.

I visited in time for Every Picture Tells a Story, with work accompanied by statements from the artists. This novel approach gave a unique insight into the artists’ intentions and the narratives in play.

5. 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.

I reckon the main edifice here, called The River, would be 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, and a library. There’s also 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.

6. 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 these 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.

Buildings include 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.

When I stopped by, the main exhibit told the compelling story of the Silvermine Art Colony (1908-1922).

7. New Canaan Nature Center

Bird Watching Gazebo at the New Canaan Nature Center

There’s 40 acres of restorative landscaped and untended greenery at the New Canaan Nature Center. On the property are an arboretum, botanical garden and nature preserve.

The landscaped spaces include a marvelous wildflower garden—I was thrilled to learn that 90% of the species growing here are native. There’s also a herb garden and a perennial border growing hepatica, Jacob’s ladder, crested iris, and bleeding heart.

Be sure to check out the 4,000-square-foot greenhouse. Meanwhile 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.

Keep an eye on the programs, with something on offer for all ages. There’s birding, hiking, after-school programs, adventure birthday parties, and more besides.

8. 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 these are juried, while the other four feature members and invited artists.

All exhibitions are open to the public and free, although there’s a suggested donation.

I’d recommend checking the website for the center’s rich array of programs. Among them are workshops in watercolors, collage and gouache, all led by professional artists.

9. Mead Memorial Park

A public space 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, pickleball 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. The entire facility is fenced and gated, for extra peace of mind.

If you’re here to relax you’ll find picnic areas, a pond and the recently opened Lodge at Mead Park. This serves breakfast, lunch and dinner, and with a lovely terrace looking over the fields.

10. Browne Wildlife Sanctuary

The New Canaan Land Trust owns a handful of sanctuaries and trails around the town. One is 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 sizable glacial erratic boulders. The property and trails were in fantastic shape when I last walked here, thanks to work by the New Canaan Scouts.

11. Summer Theatre of New Canaan

Now relocated to downtown New Canaan, this open-air tent theater sets up during June and July. In store is 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.

When I was in town there was a knockout production of Beauty And the Beast, based on the Disney animated feature.

These productions call on fresh local talent both on stage and behind the scenes, working alongside professional performers and production staff.

12. Irwin Park

If you need a dose of chlorophyll, the newest park in New Canaan is at the junction of Wahackme Road and Weed Street.

In some 40 acres, Irwin Park has come through improvements in the last decade. I enjoyed the walking/jogging trails, threading through open grassy fields, past interesting sculpture and imposing mature trees.

My perfect 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. This was 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 can be visited on tours by appointment.

13. 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. Then in winter it’s my favorite place to go ice skating in New Canaan when the lights come on.

This activity is dependent on the weather of course. Fortunately, signs on the edges will let you know when the ice is safe.

14. St Mark’s Episcopal Church

The current St Mark’s was constructed on the northern edge of New Canaan in the late 1950s. This has a Modernist design but I loved its many little nods to neo-Gothic architecture.

Accompanied by a separate bell tower, the church can seat 600 and has lots of exquisite details. They range 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.

This event features rides, games, entertainment, delicious food (strawberry shortcake of course) and the huge White Elephant Tag Sale.

15. 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 Heckscher Farm.

The galleries in the half-timbered Tudor Revival museum building are wonderfully varied, from paintings by John Singer Sargent, Warhol and Dalí to Native American artifacts, telescopes, vintage local pedal cars.

The collection is also rooted in the area, with keys and locks by Stamford’s famous Yale brand.

Also here are important collections by Stamford-related artists like Gutzon Borglum (famed for Mount Rushmore) and Reuben Nakian. As for temporary exhibitions, I was enthralled by Rachel Sard: Insofar, a vivid study of texture in painting.

On Heckscher Farm you’ll find heritage livestock breeds, as well as more exotic animals like burros, llamas and alpacas.