Get an early start to be in New Canaan for the first tour of The Glass House. Built in 1949 by architect Philip Johnson as his private residence, the striking modern home sits on 49 landscaped acres. Johnson and his partner, David Whitney, were avid art collectors, and the two-hour Glass House + Galleries Tour includes a viewing of their large-scale contemporary-art collection, featuring works by Warhol and Rauschenberg, among others.
A 20-minute drive leaves you in the center of Norwalk’s diverse dining scene just in time for lunch. El Segundo’s menu of small plates is divided into geographic regions: The Western Hemisphere, Europe and the Middle East, and the Far East; meaning, you can try Peruvian ceviche, Turkish kofte, Vietnamese spring rolls and an Antarctica-inspired Spam sandwich all in one meal. Nearby, Harlan Publick gets plenty of well-deserved accolades for its namesake burger, dripping with cheddar-ale sauce and bacon-onion jam.
Pop into Galerie Sono. The 6,000 sq ft space displays works from an array of contemporary artists, including Wolf Kahn and Hunt Slonem, whose pieces are part of permanent collections at The Metropolitan Museum of Art and the Whitney.
Before you head to Westport, take a slight detour for a stop at Speedy Donuts (named one of the nation’s top-10 doughnut shops by Grub Street), and pray they’re not sold out of glazed or old-fashioned jelly sticks.
Set your GPS for one of the following courses: Continue your art education at the Westport Arts Center, which curates a rotating roster of contemporary-art exhibits, plus interactive workshops, concerts, and events. If you’ve reached your art-saturation point, chart a course for the coast instead. Admission to Compo Beach, the perfect spot for a sandy stroll on the Sound, is free until May 1. From May to September, expect to pay a hefty fee, so opt for nearby Burying Hill Beach, which offers a stretch of sand for half the price.
Cross Westport’s American-flag-lined bridge over the Saugatuck River to enter downtown for some serious retail therapy. Main Street is lined with big-name retailers (J.Crew, Bluemercury, INTERMIX), while Post Road East is home to chic boutiques. Stop into WEST, which opened in 2016, for a mix of apparel, jewelry, and accessories from the West Coast and Australia.
Don’t even think about leaving before dinner. Rothbard Ale + Larder strikes a perfect mix with rare European beers and dishes from Germany and Central Europe (house-made sausages, hot-from-the-oven pretzels, three types of schnitzel). For something completely different, try Kawa Ni, Chef Bill Taibe’s modern izakaya, where everything from noodle dishes to craft cocktails gets a creative spin.
From May through November, make a point to see a show at the Westport Country Playhouse. The historic theater often stages works by burgeoning playwrights, and some of the world’s great actors — including Paul Newman and James Earl Jones — have graced its stage.