A day trip to New Canaan, Connecticut
New Canaan is one of my favorite towns in Fairfield County. It’s full of charm, local shops, beautiful parks, and cultural gems. With its walkable downtown, it’s the perfect place for a day trip. Here’s how to spend a quintessential day in New Canaan complete with art, great food, and plenty of local shopping.
Morning: Architecture and Design at The Glass House
Start your day with a tour of The Glass House, designed by architect Philip Johnson in 1949. This iconic modernist home sits on a 49-acre campus that includes several other stunning structures and sculptures. The Glass House building features transparent glass walls and steel framing that dissolve the boundary between inside and the surrounding landscape.
Philip Johnson was a member of the group known as the Harvard Five—alongside Marcel Breuer, Eliot Noyes, Landis Gores and John M. Johansen, who were modern architects that settled in New Canaan in the 1940s and introduced bold, experimental residential design to the region.
Tours typically last about 1–2 hours, and advance reservations are highly recommended. You’ll want to take your time walking the property between the serene reflecting pool, the Pavilion in the Pond, and the galleries, there’s unique and interesting around every corner. Tours depart right from Downtown New Canaan, where you take a shuttle directly to the property. You aren’t able to drive directly to the property!
Tip: Wear comfortable shoes for walking; the grounds are expansive and mostly gravel. Photography is encouraged, so bring your camera!
Lunch: Cherry Street Cheese
After soaking in the art and architecture, head back into town for lunch at Cherry Street Cheese, a delightful specialty cheese shop and café located in the heart of New Canaan. This charming spot offers a thoughtfully curated selection of artisanal cheeses, charcuterie, and gourmet pantry goods. Their sandwiches are crafted with high-quality ingredients and utilizie seasonal, house-made ingredients.
We opted for their Maple Mustard Turkey special with roasted turkey, Vermont cheddar, green apple, homemade cranberry mayo, greens and pickled onion. This was packed with flavor! We also had the Caveman Grilled Cheese with proscuitto, gruyere and mustard. The cozy interior is inviting, but if the weather’s nice, take your lunch outside and enjoy a little fresh-air picnic nearby.
Don’t miss: Picking up a wedge of your favorite cheese and some of their speciality products, they make perfect gifts (or indulgences for later!).
Afternoon: Shopping Downtown
Downtown New Canaan is filled with independently owned boutiques, home stores, and specialty shops which are perfect for an afternoon of browsing.
The Adirondack Store – A rustic-luxury home and gift shop offering cozy plaids, leather goods, and charming cabin-inspired decor. They also have a coffee bar in the shop, with excellent coffee and some great seasonal drinks right now.
Elm Street Books – A must-stop for book lovers. It’s one of my favorite bookstores in the state. They have an excellent selection of fiction, classics, travel guides, and thoughtful gifts, plus a friendly staff who always have great recommendations.
No. 299 – is a thoughtfully curated lifestyle brand offering a mix of distinctive, beautiful finds for the home — and for her. Guided by owner Jackie Fucigna’s love of blending old and new, each shop reflects a vintage-inspired charm that feels both approachable and fresh. They have locations in Fairfield, New Canaan, and Old Greenwich.
The Whitney Shop – A New Canaan staple since 1947, this classic gift and home store is filled with beautifully curated housewares, linens, and entertaining essentials.
As you wander Elm Street, you’ll find plenty of window displays and sidewalk seating areas perfect for people-watching with a coffee in hand.
Tips for Visiting New Canaan
Parking: The Park Street Lot (located just off Park Street near the library) is the most convenient option for downtown visitors. It’s FREE and within easy walking distance of Elm Street and most shops and restaurants. Other options are the Elm Street Lot (paid parking) or the Lumberyard Lot, across from the Glass House Visitor Center.
Timing: Arrive early for your Glass House tour to allow time for check-in and to catch the shuttle from the visitor center.
Explore More: If you have extra time, stop by Waveny Park for a stroll through its scenic trails and gardens another architectural gem designed by the same firm that built The Plaza Hotel.
A day in New Canaan is the perfect blend of art, architecture, and small-town charm. Whether you’re inspired by design, craving a good meal, or just looking for a relaxing escape from the city, this little Connecticut town delivers all of it beautifully.