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If you’re a fan of “Mad Men,’’ and all things swanky and ’60s, beware of New Canaan. This wildly upscale city in the southwest corner of Connecticut boasts one of the largest collections of mid-century modern houses in the United States. Many of them have recently sprouted “For Sale” signs — how tempting to make an offer on a fabulous Space Age-style abode in David Letterman’s old neighborhood! We should warn you that the average price for a home here is about $1.4 million.

Although New Canaan is considered a bedroom community of New York City (Manhattan is about an hour away) with the bustling train station to prove it, the city of about 20,000 is worth a visit if only to admire its architectural gems. Nearly 100 midcentury modern homes were built here in the 1950s, by noted architects like Philip Johnson and Marcel Breuer. Do your own drive-by tour, or go out with a local guide to see these Jetson-like marvels; either way, leave time to hit the Elm Restaurant for a Mad Men-inspired“Lucky Strike” cocktail. Don Draper would approve.



Named for a famous Connecticut patriot, the 1700s Roger Sherman Inn (195 Oenoke Ridge Road, 203-966-4541; www.rogershermaninn.com; rooms from $175) is the place to stay in New Canaan, with a casually elegant ambience, landscaped gardens, and award-winning dining. The inn’s French-Contemporary restaurant features dishes like Colorado rack of lamb and escargot. In nearby Southport, the Delamar Hotel (275 Old Post Road, Southport, 203-259-2800; www.delamarsouthport.com, rooms from $259) offers 44 uniquely decorated guest rooms and suites and a full-service spa. You know you’re someplace posh when you step into the lobby, with its antique marble floors, museum-quality art, and French limestone hearth. A less expensive option, just one exit north of New Canaan, is the Courtyard by Marriott Norwalk (474 Main Ave., Norwalk, 203-849-9111; www.marriott.com, from $87.) Amenities include an indoor pool and a breakfast bar, great for grabbing a yogurt parfait on the go; rooms are newly renovated and comfortable.


Rosie is a popular takeout/cafe on Elm Street.
Rosie is a popular takeout/cafe on Elm Street. Diane Bair for The Boston Globe/Globe Freelance


Everybody raves about the original fish tacos — actually, a single burrito — at Rosie (27 Elm St., 203-966-8998, most items $10-$16); don’t believe them, unless you like the blah and ordinary. A far better choice at this takeout/cafe is the vegetarian burrito, stuffed with roasted veggies and black beans and gooey with cheese ($10). Rosie’s carrot cake with cream cheese frosting ($7.50 per slice) is also locally famous, and worthy. Another New Canaan favorite is Sole’ (105 Elm St., 203-972-8887; www.zhospitalitygroup.com/sole, entrees from $15-$38), an upscale trattoria. Located next door to the movie theater, Sole serves handmade pasta dishes and wood-fired pizza beneath a sky-painted ceiling, with crisp linen tablecloths and a bar that encircles the exposed kitchen. The restaurant at the Silvermine Market (1032 Silvermine Road, 203-966-4050; www.silverminemarket.com, entrees from $17-$28) is a real find because it isn’t a restaurant: It’s a deli that morphs into a cozy (just 10 tables) eatery on weekends. The menu leans toward Italian, with dishes like Penne Vodka and Seafood Risotto, but chef-owner Scott Kaluski is justifiably famous for his root beer-braised short ribs, served with mashed potatoes and vegetables ($26); BYO wine. Open just three years, Nighttime at Silvermine is not yet discovered (you can still snag a table on a Saturday night), but it will be.


During the Day

Plan a DIY driving tour past New Canaan’s modernist gems (Laurel Road offers several examples) or book a 90-minute tour ($60) with Jack Trifero, www.modernhouseman.com, who will guide you to 12 examples of buildings created by the “Harvard Five,” Marcel Breuer, Landis Gores, Eliot Noyes, Philip Johnson, and John Johansen. You’ll also want to see the Philip Johnson Glass House (199 Elm St., 203-594-9884; www.philip
johnsonglasshouse.org, one hour tour, $30; May-Nov.), built by the architect who designed the Sony Tower and the Seagram Building in New York City, among other landmarks. The modernist campus features Johnson’s iconic 1949 glass house and 14 other buildings, including a gallery with work by Frank Stella and Julian Schnabel, among others. The New Canaan Historical Society maintains the 1960 Landis Gores Pavilion (Weed St., Irwin Park; 203-966-1776; www.nchistory.org, $5), designed by Gores. To admire some of Mother Nature’s designs, make a stop at the (free) New Canaan Nature Center (144 Oenoke Ridge Road, 203-966-9577; www.newcanaannature.org), a delightful 40-acre preserve with meadows, woodlands, a stream, marsh, and two miles of dog-friendly nature trails — even an exhibit of live birds of prey. We also like the outdoor sculpture walk at the Silvermine Arts Center (1037 Silvermine Road, 203-966-9700; www.silvermineart.org), with permanent pieces and loans from guild members. Sit alongside the pond and admire the art, or help your kids find pieces as a Sculpture Art Spy. A walk along Elm Street offers shops and boutiques (some unique shops, and some preppy perennials like Polo Ralph Lauren and J. McLaughlin) plus a good book shop, Elm Street Books (35 Elm St.) next door to Rosie. People come from far away to shop at New Canaan Thrift Shop (2 Locust Ave., 203-966-2361), where old Lily Pulitzer sheaths go to retire.


After Dark

Hard-driving Mad Ave. types are probably happy to curl up in front of the (cathode ray, no-cable) TV after a hard day at the office, and New Canaan reflects that. But you can always unwind with a glass of pinot grigio at Sole’ (see above) or a Lucky Strike cocktail at Elm Restaurant (73 Elm St., 203-920-4994; www.elmrestaurant.com.) Beyond that, there are a couple of sleek wine bars in town. Belly up to the long zinc bar at Parisian-themed Boulevard 18 (62 Main St., 203-594-9900; www.boulevard18.com) to ponder the selection of regional French wines and tasty tapas, or go Italian at grotto-like Cava Wine Bar (2 Forest St., 203-966-6946; www.cavawinebar.com), where the exposed rock walls re-create the vibe of a wine cellar in Tuscany.

New Canaan is 168 miles southwest of Boston, a 2-hour, 45-minute drive. For information, visit www.visitfairfieldcountyct.com.

Diane Bair and Pamela Wright can be reached at bairwright@gmail.com.