Travel + Leisure is exploring America one three-day weekend at a time. Here’s what to do on a short trip to the New England town of Greenwich, Connecticut.

By Adeline Duff
August 17, 2016
Perfect 3-Day Weekend in Greenwich, CT
Credit: Courtesy of Homestead Inn

Just 40 minutes away from New York City lies the affluent and picturesque town of Greenwich, Connecticut, where there’s as much to do, see, and eat as there is on Fifth Avenue—minus the hordes of tourists, honking taxis, and street peddlers. Greenwich—and many of Fairfield County’s other charming cities and towns—has been an attractive vacation destination for in-the-know New Yorkers and New Englanders for years. But more recently, its beaches, mansions, and revamped shopping and dining scene have turned the town into a hotspot for international tourists as well.

Day One

Getting to Greenwich is a quick and easy trip from Grand Central Terminal; just hop on a train via Metro North’s New Haven line, and you’ll arrive at the city center—Greenwich Avenue—in 40 minutes. Head to the Homestead Inn, a converted Victorian manor house best known for its award-winning restaurant, Thomas Henkelmann. The boutique property serves as a great base due to its close proximity to Greenwich Avenue, the city’s main shopping and dining hub, which is just a five-minute car ride away.

Spend your first day perusing Greenwich Avenue’s shops—which include Hermès, Saks, Intermix, Rag & Bone, and (much, much) more. Stop for lunch at Méli-Mélo, a local favorite known for its consistently delicious, well-priced French fare (the crêpes, juices, and soups are just a few favorites off the menu). Just off Greenwich Ave, you’ll find Consigned Couture—a thrift shop done Greenwich style (read: Chanel tweeds, mink furs, and barely worn Louboutins).

After a stop back at the Homestead Inn for an outfit change—and a glass of bubbly in the hotel’s meticulously manicured garden—head to bartaco, a restaurant in nearby Portchester, where boats can dock up directly to the outdoor patio. As the hour gets later, the crowd gets bigger—and the rock music louder—so it’s a great option for those looking for somewhere to eat, drink, and socialize.

Day Two

For those who like to start the day with a stretch, Kaia Yoga, a 10-minute drive from the Homestead Inn, offers drop-in classes for $22. Afterward, rent a car, take an Uber, or hop on the train to Westport—another upscale coastal town in Fairfield County. Have brunch at Terrain, a must-visit shop and garden café; you’ll walk out with a full stomach and an assortment of home goods and knick-knacks you never knew you needed. You can stop on the town’s Main Street if you’re in the mood for more shopping, where there are stores like West Elm, Theory, and Bluemercury.

On the way back to Greenwich, stop for lunch at Rowayton Seafood for some truffled lobster mac and cheese or their mouth-watering lobster roll. Be sure to drive along the town’s many mansions on North Street, Roundhill Road, Lake Avenue, and Taconic Road, and don’t forget to explore the Homestead Inn’s surrounding neighborhood of Belle Haven, which is one of Greenwich’s wealthiest.

Head to New York City chef Geoffrey Zakarian’s National for cocktails. While it makes for an excellent dinner option as well, we recommend spending the evening at the aforementioned Thomas Henkelmann—a true must-visit when in town.

Day Three

Start your day with a croque madame or patisserie at Versailles on Greenwich Avenue, which also serves delicious brunch options. If it’s summer, pack a picnic and head to the town’s fantastic beaches, like Greenwich Point. You can also take a short ferry ride to Great Captain Island, which is home to the 19th-century Great Captain Island Lighthouse. There, you can grill, walk its trails, and swim.

If you happen to be in Greenwich during fall or winter, cozy up at the Ginger Man, a warm, traditional-style pub with sleek wood furnishings and a fireplace. While their global selection of beers is the main draw, you can’t go wrong with their food; we especially love their fish and chips, Gorgonzola fries, and monster-sized salads.

Interested in history? Greenwich has got a lot of that, too. Stop by the Bush-Holley House and Putnam Cottage for a taste of 18th-century New England living. There’s also the Bruce Museum on Greenwich Avenue, which, depending on the season, offers a variety of art and history exhibitions.

End your stay extravagantly at L’Escale, a waterfront dining spot inside the luxurious Delamar Greenwich hotel. The restaurant serves Provençal and Mediterranean cuisine in a fine-dining setting. Be sure to sit outside to take in the harbor views while feasting on their plateau royal—a fresh selection of lobster, king crab, shrimp, and more—along with a bottle of your favorite white wine.

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