12 Best Things to Do in New Canaan, CT

by Flora Backup
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Get ready to dive into the vibrant heart of New Canaan! Our guide is your ticket to the coolest places to visit in New Canaan, from the sleek lines of the Glass House to the green paradise of Waveny Park. New Canaan is a mix of fun, culture, and nature, all wrapped up in a charming Connecticut package. Let’s start this adventure!

Welcome to New Canaan, a delightful slice of Connecticut charm! This town is a perfect blend of culture, nature, and fun.

Picture yourself wandering through the lush Waveny Park or marveling at the architectural wonder of the Glass House. In New Canaan, every corner offers something unique. From the vibrant performances at the Powerhouse Theater to the tranquil paths of Irwin Park, there’s an adventure for everyone. I’ve explored these streets and can vouch for their magic. It’s one of those top places to live in Connecticut where you can truly have it all.

Without further ado, get ready to discover some of the coolest things to do in New Canaan, Connecticut. It’s a journey you will remember!

Here's all the best things to do in New Canaan that you should know about.

Best Places to Visit in New Canaan, Connecticut

Ready to uncover the charms of New Canaan? From the architectural marvel of the Glass House to the bustling streets of downtown New Canaan, filled with unique shops and cozy cafes, there’s an abundance of exciting things to do in New Canaan.

Whether you’re strolling through the scenic Waveny Park or exploring the vibrant Carriage Barn Arts Center, every moment here is an adventure. Here’s your ultimate guide to the best activities in New Canaan – each one a must-experience!

1. Visit the Glass House

If you’re into unique architecture, the Glass House is a must-see in New Canaan. This masterpiece, designed by Philip Johnson, is more than just a house – it’s a piece of art. The transparent walls offer a stunning 360-degree view of the surrounding landscape. Trust me, it’s a photographer’s dream!

Explore the architectural masterpiece, Glass House in Connecticut, a journey through creativity, simplicity.
Explore the architectural masterpiece, Glass House in Connecticut, a journey through creativity, and simplicity.

It’s not all about the looks, though. The Glass House sits on a 49-acre property, dotted with other quirky structures, each with its own story. My advice? Take a guided tour. You’ll get fascinating insights into Johnson’s vision and the property’s history. And hey, if you’re looking for free things to do in New Canaan, the Glass House occasionally offers complimentary admission days. Keep an eye on their website for these special dates!

Remember to book in advance, as visits are by reservation only. This architectural gem in Connecticut is a journey through creativity and simplicity, a true highlight in New Canaan.

2. Stroll through Waveny Park

Waveny Park is where nature meets leisure in New Canaan. This sprawling park is a green haven, perfect for a relaxing day out. Picture this: lush gardens, walking trails, and a grand old mansion. It’s like stepping into a storybook!

Whether you're seeking relaxation or adventure, Waveny Park offers a refreshing escape for all.
Whether you’re seeking relaxation or adventure, Waveny Park offers a refreshing escape for all.

I recommend packing a picnic. Find a spot on the vast lawns or under a shady tree. The park is also fantastic for jogging or just a leisurely stroll. And if you’re into photography, the Waveny House, with its Tudor-style architecture, makes for a stunning backdrop.

For those wondering what to do in New Canaan that’s both fun and free, Waveny Park is your answer. It’s a favorite among locals and visitors alike. Whether you’re here to unwind or explore, this park is a breath of fresh air. Don’t miss out on this slice of tranquility!

3. Explore the New Canaan Nature Center

Nature lovers, this one’s for you! The New Canaan Nature Center is a little slice of wilderness paradise. With 40 acres of fields, wetlands, and woodlands, it’s a fantastic place to reconnect with nature.

The Nature Center is a hit with families, offering engaging and educational experiences. | Image Credits: New Canaan Nature Center
The Nature Center is a hit with families, offering engaging and educational experiences. | Image Credits: New Canaan Nature Center

I always find something new here, whether it’s a bird-watching trail or a blooming flower garden. The Nature Center is also a hit with families. Kids love the interactive exhibits and the chance to meet some local wildlife. And if you’re into gardening, their community garden is a sight to behold.

For those seeking beautiful places to go in New Canaan that offer both education and fun, this is your spot. It’s free to visit, though donations are appreciated. Don’t forget to check out their seasonal events. From maple syrup tapping to fall festivals, there’s always something exciting happening!

4. Enjoy a Show at the Powerhouse Theater

For a dose of culture, the Powerhouse Theater is a must-visit. Located in Waveny Park, New Canaan, this theater is a hub for vibrant performances and captivating plays. It’s where creativity comes alive!

Don't miss Powerhouse Theater—a vibrant hub for captivating plays and dynamic performances. | Image Credits: Town Players of New Canaan
Don’t miss Powerhouse Theater—a vibrant hub for captivating plays and dynamic performances. | Image Credits: Town Players of New Canaan

I’ve spent many evenings here, mesmerized by the talent on stage. The theater hosts a variety of shows, from contemporary plays to classic musicals. It’s a great way to spend an evening, especially if you’re looking for things to do at night in New Canaan.

The atmosphere is intimate, which makes every performance feel personal. Believe me, the energy here is infectious! If you’re a theater buff or just looking for a fun night out, the Powerhouse Theater delivers. Be sure to check their schedule and book your tickets in advance – these shows are popular!

5. Hike at Irwin Park

Irwin Park is a gem for anyone who loves the outdoors. This park, with its well-maintained trails and scenic views, is perfect for a refreshing hike or a leisurely walk.

Irwin Park is a must-visit for those seeking enjoyable destinations in New Canaan. | Image Credits: New Canaan Garden Club
Irwin Park is a must-visit for those seeking enjoyable destinations in New Canaan. | Image Credits: New Canaan Garden Club

Irwin Park is a beautiful and tranquil spot in New Canaan. The trails are ideal for all ages and fitness levels, which makes it a great family outing. If you’re into photography, the park’s natural beauty provides plenty of photo ops.

For those looking for fun places to visit in New Canaan, Irwin Park should definitely be on your list. It’s a wonderful spot to unwind, exercise, or simply enjoy nature. Plus, it’s dog-friendly, so your furry friend can join in on the fun!

6. Visit the Carriage Barn Arts Center

Art enthusiasts, take note! The Carriage Barn Arts Center in New Canaan is a cultural hotspot you shouldn’t miss. Housed in a charmingly restored 19th-century barn, this center showcases an array of art forms, from paintings to sculptures.

The Carriage Barn Arts Center is a cultural hotspot worth noting. | Image Credits: Carriage Barn Arts Center
The Carriage Barn Arts Center is a cultural hotspot worth noting. | Image Credits: Carriage Barn Arts Center

When you step inside, you’ll be struck by the creativity and talent on display. The exhibitions change regularly, so there’s always something new to see. It’s a great place to get inspired or even pick up a unique piece for your collection.

If you’re pondering what to see in New Canaan, the Carriage Barn Arts Center is a top choice. They often host workshops and events, which makes it a lively spot for art lovers. And the best part? Admission is usually free, making it a fantastic and affordable cultural outing.

7. Relax at Mead Memorial Park

Mead Memorial Park in New Canaan is a little sanctuary of joy and relaxation. Every time I visit, I’m reminded of how simple pleasures can bring the most happiness. This park is a blend of nature’s beauty and recreational fun.

Mead Memorial Park is the perfect spot to pause and enjoy serene vibes. | Image Credits: New Canaan Chamber of Commerce
Mead Memorial Park is the perfect spot to pause and enjoy serene vibes. | Image Credits: New Canaan Chamber of Commerce

The park’s charm lies in its versatility. Fancy a game of baseball or tennis? You’ve got top-notch facilities here. But if tranquility is your thing, the pond area, with its gentle breezes and rustling leaves, is blissful. I recommend bringing a picnic – there’s nothing like a lazy lunch under the Connecticut sky.

If you’re looking for fun places to visit in New Canaan where you can just chill out and enjoy nature, Mead Memorial Park is it. It’s a lovely spot to take a break from your busy itinerary and soak in some peaceful vibes. Plus, there’s ample space for everyone, so it never feels crowded.

8. Play Golf at the Country Club of New Canaan

Golf enthusiasts, you’re in for a treat at the Country Club of New Canaan. This place is a golfer’s paradise with lush fairways and challenging greens. I’ve played here a few times, and each round is as enjoyable as the last.

Country Club of New Canaan is a prime destination for sports enthusiasts. | Image Credits: Country Club of New Canaan
Country Club of New Canaan is a prime destination for sports enthusiasts. | Image Credits: Country Club of New Canaan

The course is well-maintained, offering a great experience for both beginners and seasoned players. The rolling hills provide a picturesque backdrop, which makes your game even more enjoyable. And if you’re looking to improve your swing, their pro shop staff are super helpful.

After your game, the clubhouse is the perfect spot to relax and chat with fellow golfers. For those looking for where to go in New Canaan for a day of sport and relaxation, this golf course is a top pick. It’s a blend of sporty challenge and serene beauty, a must-visit for any golf lover.

9. Explore the Silvermine Arts Center

The Silvermine Arts Center is a creative hub that’s close to my heart. It’s a place where art comes alive in New Canaan. With its galleries, studios, and art classes, it’s a haven for anyone with a love for creativity.

For family-friendly fun in New Canaan, explore creative workshops at Silvermine Arts Center. | Image Credits: Silvermine Arts Center Tripadvisor
For family-friendly fun in New Canaan, explore creative workshops at Silvermine Arts Center. | Image Credits: Silvermine Arts Center Tripadvisor

Walking through the galleries, you’ll find inspiring works by local and regional artists. It’s a great way to get a sense of the vibrant art scene in New Canaan. I always find something that catches my eye and sparks my imagination.

If you’re looking for fun things to do in New Canaan with kids, consider taking a workshop here. They offer classes in painting, sculpture, and more, suitable for all skill levels. It’s not just about viewing art. It’s about getting hands-on and expressing your own creativity. Trust me, a visit to the Silvermine Arts Center is a fulfilling experience for any art lover.

10. Attend the Annual New Canaan Village Fair & Sidewalk Sale

Every year on the third Saturday in July, New Canaan buzzes with the excitement of its Village Fair & Sidewalk Sale. This isn’t just any event. It’s a tradition dating back to the 1920s, bringing together the community in a vibrant celebration.

The Annual Village Fair is New Canaan's must-visit experience. | Image Credits: New Canaan Chamber of Commerce
The Annual Village Fair is New Canaan’s must-visit experience. | Image Credits: New Canaan Chamber of Commerce

Wandering through the fair, you’ll feel the history and community spirit that have been its backbone for nearly a century. The streets are lined with everything from unique handmade crafts to stylish boutique clothing. It’s a treasure trove for shoppers and a fantastic way to support local artisans and businesses.

And let’s talk about the food – it’s a festival in itself! From gourmet bites to classic street eats, your taste buds are in for a treat. If you’re looking for cool things to do in New Canaan, this fair is a must. It’s a perfect blend of history, community, and fun, all wrapped up in one lively day.

11. Dine at Local Restaurants

If you’re on the hunt for unique restaurants in Connecticut, New Canaan’s dining scene is a foodie’s dream. With a variety of restaurants, there’s something to satisfy every palate. From cozy cafes to upscale dining, each spot offers a unique flavor of the town.

Indulging in local eateries ranks among the most amazing activities in New Canaan. | Image Credits: Sole Tripadvisor
Indulging in local eateries ranks among the most amazing activities in New Canaan. | Image Credits: Sole Tripadvisor

One of my personal favorites is Sole Ristorante on Elm Street. Their Italian cuisine is authentic and mouth-watering. For a classic American diner experience, New Canaan Diner on Forest Street is a must-visit. Their hearty meals feel like a warm hug!

If you’re into healthier options, Green & Tonic on Burtis Avenue is a great choice. Their fresh, organic offerings are both delicious and nutritious. Take it from me, exploring the local eateries is one of the most amazing things to do in New Canaan. Each restaurant brings its own charm, which makes dining here an adventure in itself.

12. Downtown New Canaan Shopping

Last up on our list of New Canaan’s best things to do is go shopping downtown. This vibrant area is a delightful mix of unique shops, high-end boutiques, and everything in between. It’s the perfect place to find that special something, whether it’s for yourself or a gift for someone else.

Explore downtown New Canaan for a diverse shopping experience, blending unique shops and high-end boutiques. | Image Credits: Unlocking Connecticut
Explore downtown New Canaan for a diverse shopping experience, blending unique shops and high-end boutiques. | Image Credits: Unlocking Connecticut

Strolling through downtown, I’m always amazed at the variety. You can find cutting-edge fashion, charming home decor, and even specialty stores that are sure to surprise you. And the best part? It’s all walkable. You can enjoy dinner, catch a movie, and indulge in some retail therapy without ever needing your car.

During spring and holidays, downtown New Canaan transforms into a festive hub with sidewalk sales and community events. It’s a lively atmosphere that’s not to be missed. My advice? Spend an afternoon here, maybe treat yourself at a day spa, and soak in the local charm. A visit to downtown New Canaan is all about experiencing the heart and soul of the town.

Frequently Asked Questions (FAQs) about the Best Things to Do in New Canaan, Connecticut:

Looking for more content on things in New Canaan to do? Here are some popular questions (and answers) I get that will help you plan your trip to New Canaan, CT.

Is New Canaan expensive?

New Canaan is known for its upscale charm, which is reflected in its cost of living and dining. While it’s not the most budget-friendly town to live in New England, you can find a range of options. For dining, there are upscale restaurants as well as more affordable cafes. In terms of shopping, alongside high-end boutiques, there are local shops offering a variety of goods at different price points. My tip? Enjoy the free attractions in New Canaan like the parks and nature trails to balance your budget.

Does New Canaan have a downtown?

Yes, and it’s a highlight! Downtown New Canaan is a bustling area with a fantastic mix of shops, restaurants, and entertainment options. It’s walkable, vibrant, and perfect for a leisurely stroll, shopping, or dining. The downtown area really captures the town’s friendly and welcoming spirit.

Prepare to explore some of the most exciting activities in New Canaan, Connecticut—an unforgettable journey awaits!
Prepare to explore some of the most exciting activities in New Canaan, Connecticut—an unforgettable journey awaits!

What is the closest airport to New Canaan CT?

The closest major airport to New Canaan is Westchester County Airport, about 20 miles away. It’s convenient for domestic flights. For international and more extensive domestic flights, LaGuardia Airport in New York is about 40 miles away. I recommend considering your destination and flight options to choose the best airport for your trip.

What is the history of New Canaan?

New Canaan’s history is rich and fascinating. Originally an agricultural community, it transformed into a bustling town with the arrival of the railroad in the 19th century. It’s known for its significant role in the modern architectural movement of the 20th century, with landmarks like the Glass House. The town has beautifully preserved its historical roots while evolving into a modern, vibrant community.

Why is it called New Canaan?

The name “New Canaan” is thought to be inspired by the biblical land of Canaan, symbolizing a new promise and hope. The town was named by its Puritan settlers in the 18th century, reflecting their religious aspirations and the idea of starting a new life in a promising land.

The top things to do in New Canaan for all types of travelers
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