Things to Do in New Canaan, CT: Most Unique Spots

The Philip Johnson Glass House, one of the most famous things to do in New Canaan, CT

New Canaan, Connecticut is one of those quintessential New England towns. This quaint town brims with history, stunning architecture, and a close-knit community spirit. Just a stone’s throw away from New York City, it has a trove of activities and attractions. Here, you can marvel at iconic structures such as the Philip Johnson Glass House, unwind in scenic parks, or partake in vibrant seasonal events. New Canaan is one of the wealthiest towns in the US. It’s also famous for the Silvermine Arts Center and the Harvard Five. This group of Modernist architects left an indelible mark on the town’s residential landscape in the 1940s and 50s. A visit to the charming town center is a must, with its chic boutiques and exquisite restaurants. The town is also dotted with immaculate parks, cultural exhibits, and recreational areas, making it a perfect getaway destination.

 

So buckle-up as we explore the best things to do in New Canaan, CT.

Quick hits

  • Explore New Canaan’s captivating history and modern amenities!
  • From the Philip Johnson Glass House to trendy shopping boutiques, there’s something for everyone.
  • Enjoy outdoor adventures, art installations, seasonal festivities & more in this Connecticut destination!

A Brief New Canaan History

Old postcard of the New Canaan train station

1731 was the year when the colonial legislature of Connecticut decided to shake things up a bit. And thus Canaan Parish was born as a religious entity. They took land away from the northwestern corner of Norwalk and the northeastern edge of Stamford. The sparse families who had made their homes in the area were granted the right to form a Congregational church. By the time 1801 rolled around and New Canaan was officially incorporated, it found itself lacking a central common, a main street, or even a town hall.

Industrial Era

The town was primarily an agricultural hub until the Revolutionary War. However, post-war, the people of New Canaan found a new calling: shoemaking. As the shoe industry flourished, regional settlements began to develop into distinct district centers, including:

  • Ponus Ridge
  • West Road
  • Oenoke Ridge
  • Smith Ridge
  • Talmadge Hill
  • Silvermine

The arrival of the New York, New Haven, and Hartford Railroad in 1868 brought with it a new breed of residents. That is, wealthy city dwellers seeking a summer retreat amidst the pastoral beauty of New Canaan. Many of these summer visitors decided to stay permanently, commuting to their jobs in New York City. One such settler was Lewis Lapham, founder of Texaco and great-grandfather of Harper’s Magazine editor Lewis H. Lapham. He spent his summers at the family estate, which is now the sprawling 300-acre Waveny Park.

 

In the 1890s, editor Will Kirk of the Messenger ruffled a few feathers when he dubbed New Canaan the “next station to hell”. The locals (eventually) took it in stride. And some continue to use the term today, either as a joke or a serious comment, depending on their current feelings towards New Canaan.

Post Wold War II

The town became a significant center of the modern design movement from the late 1940s to the 1960s, with around 80 modern homes built. The Harvard Five, a group of students and teachers from the Harvard Graduate School of Design, settled here because real estate was cheap. And they used the land to build homes that were the antithesis of traditional build. Other architects, such as:

  • Frank Lloyd Wright
  • Victor Christ-Janer
  • John Black Lee
  • Allan Gelbin
  • Hugh Smallen

 

Also contributed significant modern houses. Some of these architectural marvels were destroyed by buyers who replaced them with generic new builds. Some have been saved from the wrecking ball, and are now open to the public.

 

With its annual holiday stroll and close proximity to New York City, New Canaan is a must-visit destination for travelers seeking an experience that is both unique and memorable.

The Best Things to Do in New Canaan, CT

A view of New Canaan, Connecticut, with the Silvermine Arts Center, Grace Farms, Waveny Park, and the Philip Johnson Glass House in the background

Behold New Canaan, Connecticut, a place where boredom is as rare as a cat that barks. This town has an attraction for every soul, and a soul in every attraction. Let’s take a gander:

  • The Philip Johnson Glass House – a testament to a man’s audacity to live in a see-through home.
  • Parks so beautiful, they’d make a poet out of a mute.
  • Art and culture experiences that could make a stone statue weep.
  • Shopping opportunities that would make even the most frugal of hearts skip a beat.

 

This is no ordinary Connecticut community, my friend. This is New Canaan – a place where architecture, nature, and chic boutiques unite to cater to the whims and fancies of every wanderer.

 

So whether you’re an admirer of human ingenuity, a lover of nature’s grandeur, or a seeker of rare treasures, rest assured, New Canaan has got you covered.

Philip Johnson Glass House

Interior of the art gallery

A visit to New Canaan wouldn’t be complete without a stop at the iconic Philip Johnson Glass House. This landmark of modern architecture showcases the innovative design of the 20th century, offering various tours that explore its impressive collections of contemporary art and immaculate grounds. Tours begin and conclude at the Visitor Center in Downtown New Canaan, with options ranging from a succinct one-hour exploration to a comprehensive 2.5-hour weekend experience.

St Mark’s Episcopal Church

For a dose of awe-inspiring architecture and a sense of serenity, make sure to visit St Mark’s Episcopal Church. This neo-Gothic-inspired church features magnificent stained glass, a one-of-a-kind free-standing altar, and a stunning floor-to-ceiling reredos with a bronze sculpture by Clark Fitzgerald.

 

The church annually hosts the May Fair, featuring rides, games, entertainment, mouthwatering food, and the famous May Fair White Elephant Tag Sale. It makes a great excuse to swing by here in the month of May.

Grace Farms

The excellent organic cafe at Grace Farms

Grace Farms, a place that doesn’t ask for your dime but your time, is a sanctuary. It’s a non profit center dedicated to celebrating the arts, nature, justice, community, and faith.

 

It’s a place where these five elements don’t just coexist but thrive together, like a well-conducted orchestra. They honor nature, the arts, community, justice, and faith. With attractions like:

  • a 700-seat amphitheater
  • a tea pavilion
  • a library
  • a communal space with an excellent organic café
  • A sunken court for recreation and performing arts

 

Grace Farms offers a plethora of activities and areas to discover.

 

Visitors can also discover delightful contemporary art installations from Teresita Fernández, Olafur Eliasson, and Thomas Demand, adding to the captivating atmosphere of this unique space.

Waveny Park

rose garden at Waveny Park

Should you find yourself yearning for a dalliance with Mother Nature, then set your compass for Waveny Park. Once the playground of the Lapham dynasty, this public treasure now offers:

  • Jogging and walking trails
  • Sports fields
  • Picnic areas
  • The magnificent Waveny House, a “castle” built in 1912

 

Waveny Park is also home to various town-wide events, such as concerts and festivals, making it a hub for community activities. I hate to use the term, hidden gem, as it gets overused these days, but this place is really awesome.

Carriage Barn Arts Center

For a dose of local art and culture, head to the Carriage Barn Arts Center. Housed in a stunning 19th-century stone barn, this gallery and performing arts venue showcases local talent. It also offers workshops taught by professional and local artists.

 

Hosting eight exhibitions every year, half of which are juried and the other half showcasing members and guest artists, the Carriage Barn Arts Center consistently presents new and thrilling exhibits.

Downtown New Canaan

Downtown New Canaan, home of the New Canaan Chamber of Commerce and trendy boutiques

When you find yourself in New Canaan, a leisurely saunter through the heart of town is not a suggestion, it’s a requirement. Downtown New Canaan, with its easily navigable streets and one-of-a-kind boutiques, spills over with that classic New England allure.

 

Don’t miss out on Elm Street, the town’s lifeblood, where a smorgasbord of tantalizing eateries, modish boutiques, and thought-provoking art galleries awaits your discovery.

Mead Memorial Park

Mead Park, also known as Mead Memorial Park, is another outdoor gem in New Canaan. It offers:

  • Baseball fields
  • Tennis courts
  • Pickleball courts
  • Playscape facilities

 

This town park is a perfect place to enjoy some quality family time.

 

And don’t forget about Fido – he’s welcome too at Spencer’s Run Dog Park, as long as he’s on a leash.

Irwin Park

Sculture at Irwin Park

For those in search of a tranquil oasis amidst the hustle and bustle, Irwin Park is your ticket. Spanning 36 acres of New Canaan’s verdant landscape, this park is a sanctuary for the soul. It boasts:

  • Trails that beckon the weary traveler to walk or jog, whispering tales of nature in your ear with each step.
  • A sculpture that stands proud, a silent sentinel challenging the sky.
  • Mature trees that have withstood the test of time, their gnarled branches creating a canopy of serenity.
  • The Modernist Gores Pavilion, a structure that defied fate and escaped the cruel jaws of the wrecking ball.

 

In this idyllic haven, you can unwind and drink in the unspoilt beauty of New Canaan. The trails, whether you choose a leisurely stroll or a brisk jog, are your pathway to peace.

Mill Pond Park

Mill Pond Park, a chameleon of a spot, is just the ticket for summer picnics, a quiet afternoon with a good book, or a fishing derby for the young ones come spring.

 

When winter descends, the park dons a snowy mantle, transforming into a magical ice rink that’s perfect for rustic ice skating. No matter the season, Mill Pond Park is a charming refuge, a place that welcomes all visitors with open arms, regardless of their age.

Silvermine Arts Center

Mead ParkArt enthusiasts will adore the Silvermine Arts Center. As an art school and exhibition space, it offers courses, symposia, panel discussions, and outreach workshops in a variety of disciplines, including watercolors, collage, and gouache.

 

With its five galleries and important collections, Silvermine Arts Center provides a unique opportunity to experience the local art scene in New Canaan.

New Canaan Historical Society

Dive into New Canaan’s history at the New Canaan Historical Society, which features eight museums and historic buildings, including:

  • The Little Red School House
  • The Gores Pavilion
  • The Rock Schoolhouse
  • Cody Drug Store
  • The Town House
  • The Hanford-Silliman House
  • The Rogers Sculpture Studio
  • The Tool Museum and Printing Office

 

It’s a fantastic way to learn about the town’s past while exploring its charming streets.

New Canaan Nature Center

Trees at the New Canaan Nature Center

The New Canaan Nature Center, supported by the New Canaan Land Trust, offers 40 acres of landscaped and untended greenery. Sites in an extensive botanical garden include:

  • A wildflower garden
  • Herb garden
  • Perennial border
  • Two ponds
  • Nature preserve
  • Greenhouse
  • Historic orchard

With its walking trails, picturesque ponds, and lush botanical garden, it’s the perfect spot for an afternoon of exploration and relaxation.

Browne Wildlife Sanctuary

Discover the natural beauty of New Canaan at the Browne Wildlife Sanctuary. This 10-acre woodland features interpretive boards about geology, ecology, and human uses of the site, making it an educational and delightful experience for the entire family.

Summer Theatre of New Canaan

Experience the magic of live theater at the Summer Theatre of New Canaan. Presenting Broadway shows and performances for all ages, this outdoor theater showcases local talent and professionals in a vibrant and engaging atmosphere. Don’t miss the chance to enjoy a memorable evening under the stars.

New Canaan Farmer’s Market

A visit to the New Canaan Farmer’s Market is a must for any food lover. From May to November, this lively market offers fresh local produce, artisanal goods, and a friendly community atmosphere, making it an essential stop during your visit to New Canaan.

 

The New Canaan Farmer’s Market is a hub for local farmers and food lovers. With fresh produce, locally-sourced products, and a bustling atmosphere, it’s a must-visit for food enthusiasts and supporters of local businesses.

Seasonal Events and Festivals in New Canaan, CT

New Canaan is a town that loves to celebrate, and its seasonal events and festivals are no exception. Here are some of the events you can look forward to:

  • Family Fourth Fireworks for Fourth of July fireworks
  • Annual Fall Fair
  • Harvest Festival
  • All Hallows Eve Parade
  • Holiday Stroll
  • Village Fair and Sidewalk Sale
  • Glow Wild Lantern Festival

 

There’s always something happening in this vibrant community.

 

One of the most anticipated events is the New Canaan Halloween Parade, where kids in costumes, live music, and entertainment take over Elm Street for a day of spooky fun.

New Canaan Halloween Parade

The New Canaan Halloween Parade is a beloved annual event that brings the town together for a day of festive fun. Taking place on the Sunday before Halloween, this spooktacular parade features:

  • Kids in costumes
  • Live music
  • Entertainment
  • A “Howloween Dog Parade” for the town’s furry friends

Shopping in New Canaan, CT

Adirondack Store & Gallery, one of the trendy boutiques in the town center

New Canaan offers a shopping experience like no other – with its walkable downtown district and unique boutiques, you’ll find something for everyone. From trendy clothing stores to charming bookshops and inspiring art galleries, there’s no shortage of local treasures to discover.

 

Personal favorites here include:

  • The Adirondack Store & Gallery has become my secret spot for buying holiday ornaments
  • Elm Street Books is popular for its selection

 

Whether you’re on a quest for the ideal gift or indulging in some self-pampering, New Canaan’s shopping scene will not disappoint.

Restaurants in New Canaan, CT

From cozy breakfast spots to elegant dinner venues, New Canaan boasts a diverse range of dining options to suit every palate. Whether you’re in the mood for a delicious meal with friends, a romantic date night, or a quick bite on the go, this Connecticut town has something for everyone.

Breakfast in New Canaan

Start your day off right with a scrumptious breakfast in New Canaan. Popular spots like Rosie and Silvermine Market offer a mouthwatering selection of morning meals, including:

  • Omelets
  • Pancakes
  • French toast
  • Breakfast sandwiches

 

With a welcoming atmosphere and delicious food, it’s no wonder Rosie and Silvermine Market are local favorites.

Lunch & Dinner in New Canaan

New Canaan’s lunch and dinner scene is equally as impressive, featuring restaurants such as Elm, Spiga, and the historic Roger Sherman Inn. With a variety of cuisines on offer, you’ll be spoiled for choice when it comes to deciding where to dine.

 

Whether you have a hankering for Italian, American, or a fusion of the two, New Canaan will satisfy your appetite.

Hotels, Inns, & Places to Stay in New Canaan, CT

Entrance to Mead Park

So you’re thinking of venturing to New Canaan, eh? Well, you’re in luck, my friend. This gem of Fairfield County is a mere 25-minute jaunt from our humble abode, our bed and breakfast in Greenwich, Connecticut. So fuel up the old jalopy, and get ready for a New England adventure you won’t soon forget.

 

You can also explore hotels in Norwalk, CT, including the Inn at GrayBarns on the Silvermine River. Or check out hotels in Stamford, Connecticut.

 

If you’d rather stay in the town of New Canaan, you’ve got a solid choice:

Roger Sherman Inn

The Roger Sherman Inn, named after the one and only Roger Sherman, is a charming bed and breakfast in New Canaan that features 15 luxurious guest rooms and six grand dining rooms. Established in 1925, this historic inn offers French-inspired American cuisine and an expansive wine list, ensuring an unforgettable dining experience during your stay.

Directions to New Canaan

The drive from Greenwich, CT, to New Canaan only takes about 25 minutes or so. You get the pleasure of driving along North Street and onto the Merritt Parkway from here.

 

Train trips from NYC are even easier, though you have to switch trains at the station in Stamford, Connecticut.

More Towns and Cities to Explore Near New Canaan, Connecticut

Venturing out from New Canaan, you’ll find a wealth of nearby towns and cities in Fairfield County to explore, each offering its own unique attractions and experiences. Some of the nearby towns and cities to visit in Connecticut include:

  • The city of Stamford, Connecticut: a bustling city with a vibrant downtown area and a variety of shopping, dining, and entertainment options.
  • Norwalk, Connecticut: a coastal paradise with beautiful beaches, waterfront parks, and a lively arts and culture scene.
  • The town of Darien, CT: a charming small town known for its picturesque neighborhoods, historic sites, and outdoor recreational opportunities.

 

There’s no shortage of amazing sights and activities to discover in Connecticut.

 

Be it a day trip or a weekend escape, Connecticut is ready to accommodate your plans.

Stamford, CT

As the largest city in Fairfield County, Stamford is a bustling hub of activity with a vibrant downtown area that’s sure to impress. Visit the Stamford Museum & Nature Center, the Bartlett Arboretum & Gardens, and the Stamford Historical Society to get a taste of the city’s rich history and natural beauty.

 

And don’t forget to explore Stamford’s diverse shopping and dining scene, perfect for a day of indulgence.

Norwalk, Connecticut

For a coastal adventure, head to Norwalk, where you’ll find beautiful beaches, boating spots, and the Maritime Aquarium. Perfect for family fun, Norwalk offers a variety of attractions, including the Lockwood-Mathews Mansion Museum and the Norwalk Historical Society.

 

This is also one of the most happening places near New Canaan, especially the South Norwalk borough of town.

Darien, CT

Darien, part of Connecticut’s “Gold Coast,” offers a small-town waterfront lifestyle with top-notch schools and pristine land and waters. This picturesque town is perfect for those seeking a cozy suburban community.

 

Explore the best things to do in Darien, CT, like: Darien Nature Center, the Darien Historical Society, and the Darien Arts Center to get a sense of the town’s charming atmosphere.

Tl;dr

From its rich history and stunning architecture to its vibrant community events and beautiful parks, New Canaan, Connecticut, truly has something for everyone. Whether you’re an art enthusiast, nature lover, or simply looking for a charming New England getaway, this idyllic town is sure to leave a lasting impression. So, get ready to explore the hidden gems of New Canaan – a picturesque destination that promises an unforgettable experience.

Frequently Asked Questions

What is New Canaan CT known for?

New Canaan CT is known for its modernist homes and is home to The Philip Johnson Glass House, considered architect Philip Johnson’s signature work. It remains a wealthy rural enclave with over 80 homes designed by the Harvard Five in the 1940s.

How is New Canaan?

New Canaan is a charming mix of colonial history and modern living, making it an ideal home for commuters to NYC or New Haven. Its culture and community are vibrant and alive, giving it a unique atmosphere.

What towns border New Canaan CT?

New Canaan CT is bordered on the south by Darien, west by Stamford, east by Wilton, southeast by Norwalk, and north by Lewisboro and Pound Ridge in Westchester County.

What are the must-see attractions in New Canaan, Connecticut?

If you’re in New Canaan, you must check out the Philip Johnson Glass House, Waveny Park, Carriage Barn Arts Center and New Canaan Nature Center for an unforgettable experience.

Are there any seasonal events or festivals in New Canaan?

New Canaan has plenty of seasonal festivities to enjoy, such as the Harvest Festival, Holiday Stroll, Village Fair and Sidewalk Sale, and Glow Wild Lantern Festival.