Just a 40-minute train ride from Grand Central Station, Greenwich, Connecticut typically lives in the shadow of New York City, overlooked as a tourist destination and branded little more than a wealthy suburb of the city. But this stately town on the New York-Connecticut border is hardly the doldrums of suburbia. Envy-inducing mansions rise on hillsides that are peppered with pre-Revolutionary historic sites. Manhattan represents—albeit in a lighter fashion—along Greenwich’s principal thoroughfare, “the Ave.,” which is punctuated by recognizable high-end retailers and upscale restaurants. Meanwhile, nearby Old Greenwich feels lost in time with 19th-century architecture and mom-and-pop stores. Best of all, though, is Greenwich’s unspoiled nature. Birdlife rules on Great Captain’s Island and beautiful beaches edge the uninhabited peninsula of Greenwich Point Park. At its core, this is New England inhabited by New Yorkers, where urbanites can take a breather.
CHECKING IN
For your Greenwich home base, choose the family-owned, waterfront Delamar Greenwich Harbor, one of the top New England hotels in the 2016 Condé Nast Traveler Readers’ Choice Awards. Request a Harbor view room at the 82-key hotel, which is within walking distance of “the Ave.” and opposite the Arch Street ferry dock, the point of departure for seasonal service to Island Beach and Great Captain’s Island. There’s a generous pour of Laurent-Perrier champagne at check-in and complimentary wine and cheese on weekend evenings.
Alternatively, sleep among the mansions and manors of Belle Haven at Homestead Inn–Thomas Henkelmann. Henkelmann’s award-winning contemporary French restaurant anchors this Relais & Châteaux property, where his wife, Theresa, designed the 18 rooms of the 19th-century manor and carriage house. Grand Luxury Suites come adorned with singular antiques and artifacts (e.g. the olive green Room 124 with beaded African masks and hand-carved crown moulding from Morocco).
DAY ONE: SHOP THE AVE.
Get to Greenwich by early afternoon to avoid rush hour mayhem and to do a little shopping (it’s lights off at most stores by 6 p.m.). After check-in, stroll the mile-long Ave. with stops at Richards, a classic department store that remains family-owned; the sole U.S. outpost of Togas, a luxury Greek home textile store; Winston Flowers, a New England-based flower shop where floral displays transcend art; and Betteridge, a family jeweler in Greenwich since 1952 that’s nationally known for its watch collection.
For dinner, book ahead at l’escale for excellent ocean-to-table Mediterranean food and a side of the Greenwich “scene.” Executive chef and Frenchman Frederic Kieffer makes an amazing bouillabaisse Provençal (stocked with branzino, monkfish, scallop, rock shrimp, and mussels) and Duck “a l’Orange” with whipped rutabaga and Brussels sprout duck slaw. Pre- or post- dinner, grab a cocktail in the adjacent lounge, where each drink is named after a black-and-white film. (We love the “How to Marry a Millionaire”: house-made berry Belvedere vodka, elderflower liqueur, and lychee.)
DAY TWO: OLD GREENWICH & FINE DINING
Start your day by heading to Old Greenwich, a neighborhood dating to 1640, and its picturesque, single-street downtown. Grab breakfast to go or sit down for a bigger brunch at small-batch bakery and coffee roaster Sweet Pea's Baking Company. We’re still thinking about the banana crumb muffins, the Nutella doughnuts sprinkled with hazelnuts, and the caramel cinnamon buns topped with a scoop—no going back now—of cream cheese frosting. Walk the carbs off by weaving in and out of the mom-and-pop shops: Back 40 Mercantile, a new take on an old-fashioned general store, sells regionally made candles and ceramics and hyper-local products like “Ggachis,” handmade Tootsie rolls.
Drive south to Greenwich Point Park—known locally by the name of its most scenic lookout, Tod’s Point—for the all-season beaches of this unspoiled peninsula. (The New York City skyline is visible from here on a clear day.) If you're traveling with kids in tow, consider renting an oh-so-Old-Greenwich Dutch Box Bike (think: a bike-wagon hybrid from the Netherlands) to explore the park. In the warmer months, expect to spend more time at Tod’s Point, where the community sailing club offers kids’ sailing lessons and adults can rent paddle boards. (Note that a park/beach pass from the Department of Parks and Recreation is required during peak summer months.)
If the weather doesn’t cooperate, visit the Bush-Holley historic site, a house-turned-museum built in 1728 that later became the center of Connecticut’s first art colony in the late 19th century. This is where Impressionism took off in America with artists like Childe Hassam in residence.
Save your appetite for a multi-course meal at standout French restaurant Thomas Henkelmann. A recent menu included Perigord black truffles royale with Maine lobster bisque and lobster ragout (that's just the starter) and Atlantic Halibut filet in a potato crust. The warm Valrhona chocolate soufflé cake topped with house-made pistachio ice cream and candied pistachios didn’t disappoint, either.
DAY THREE: BRUNCH & BROWSE
Finish off the weekend with a bit of pampering at The Spa at Delamar. Since it’s the best of its kind in Greenwich and often booked out by locals, we recommend scheduling a treatment in advance. Facials are the main draw here—and why wouldn't they be when they're named “Vitality of Glaciers Pamper Your Skin"?
Post facial or massage, grab brunch back where you started—on the Ave. Go to The National, the latest restaurant from celebrity chef and TV personality Geoffrey Zakarian, where breakfast classics get an Iron Chef makeover. (Sweet potato duck hash and omelets stuffed with marinated artichoke, piperade, ricotta salata? Yes, please.) A few bellinis or Bloody Marys later, walk over to the Bruce Museum of Arts and Science. This small museum makes a big impression with its world-class rotating art and natural history exhibitions, which, until July 16, 2017, includes “Last Days of Pangea: In the Footsteps of Dinosaurs,” highlighting pre-historic discoveries from the modern-day Connecticut Valley.
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