Start from 20 curated places around New Canaan, CT, then choose the recommendations that fit your guests.
Restaurants & cafés
Sole
A bright, modern Italian eatery at the center of Elm Street that has earned a loyal following for its handmade pastas and prosciutto-wrapped cod. The freshly renovated dining room balances high-end finishes with a relaxed, buzzy atmosphere — good for date nights or group dinners. The parmesan-crusted halibut and yellowfin tuna crudo are reliable standouts.
Hashi Sushi
A sleek Japanese restaurant a block from downtown that earns consistent praise as the best sushi outside Manhattan in this corridor. Fish comes in exceptionally fresh, the omakase-style nightly specials change often, and the dining room's clean aesthetic matches the precision of the kitchen. Hibachi plates round out the menu for those who want cooked options.
Trails & outdoors
Waveny Trail
An easy 1.3-mile loop through the manicured Olmsted-designed grounds of Waveny Park, passing the Tudor mansion, lawns, and woodland edges with minimal elevation change. With 433 AllTrails reviews and a 4.5-star rating it is the most-used trail in New Canaan, and deservedly so — the historic setting and open landscape make it feel special for what is essentially a town park walk.
Silvermine-Fowler, Kelley Uplands & Hicks Meadow Preserve
A 1.7-mile easy loop through three connected land trust preserves in the Silvermine neighborhood, rated 4.6 stars from 98 AllTrails reviews. The trail weaves through birch and oak woodland, along a seasonal stream, and across open meadow — a genuinely quiet, nature-immersive walk that feels remote despite being minutes from downtown. Good for birding, particularly in spring.
Things to do
Silvermine Arts Center
One of the oldest artist guilds in the United States, founded in 1922 on the Silvermine River, with five galleries presenting more than 20 exhibitions per year across painting, sculpture, photography, and craft arts. The School of Art runs workshops for all levels, and the outdoor Sculpture Walk blends art into the wooded landscape. A genuine arts campus rather than a typical gallery, and free to visit.
Carriage Barn Arts Center
A restored 19th-century stone carriage barn in the heart of Waveny Park, now operating as New Canaan's Society for the Arts gallery. Free rotating exhibitions of local and regional artists run year-round alongside small theatrical performances and workshops. The building itself — fieldstone walls, timber beams, double-height gallery — is worth seeing as an architectural conversion.
Landmarks & sights
The Glass House
Philip Johnson's landmark 1949 residence — a steel-framed rectangle of plate glass set in 49 acres of sculpted Connecticut landscape — is the defining monument of mid-century modernism in New England. The tour covers the main house and up to 13 additional structures including a sunken sculpture gallery and a painting gallery designed like a volcanic crater. Visitor numbers are deliberately capped, making every tour feel intimate.
Waveny Park
A 300-acre former private estate gifted to the town, anchored by a 1912 Tudor-style mansion designed for the co-founder of Texaco. The Olmsted Brothers laid out the sweeping lawns and plantings — the same firm behind Central Park — and today the park holds walking trails, rose gardens, tennis courts, a dog park, and the Carriage Barn gallery. Free admission and open year-round.