For the 50+ Traveler

Greenwich, Connecticut, is just a 40-minute ride on the Metro-North Railroad’s New Haven Line from New York City’s Grand Central Terminal. Not simply a bedroom community of Manhattan, Greenwich offers history, art, culture, food, shopping, and amazing scenery all wrapped up in an appealing and elegant package. It consists of a charming downtown, historic neighborhoods, and a “backcountry” full of golf courses, horse farms, reclusive celebrities, and financial titans.

It’s easy to spend an amazing day in historic Greenwich. Here are just a few ideas.

What To Do In Greenwich

Greenwich surprises many visitors who think of it as a sleepy little town full of quaint old buildings. In reality, it’s a hive of activity with lots to do.

The Bush-Holley House in Greenwich.

Check Out The Bush-Holley House

Art lovers will enjoy this historic center of American Impressionist art. The Bush-Holley House held the first art colony in Connecticut and originally served as a boarding house in the Cos Cob neighborhood. John Henry Twachtman, Theodore Robinson, J. Alden Weir, Childe Hassam, Ernest Lawson, other prominent Impressionists, and scores of students flocked there to hone their craft, especially painting in the open air.

The Greenwich Historical Society keeps the history and art alive with exhibits, artifacts, tours, and a new museum building showcasing even more Greenwich history.

Visit Bruce Museum And Bruce Park

We love exploring indoors and out, and the Bruce Museum and Bruce Park offer double the fun. Start inside with the incredible museum that integrates art, natural and global environmental history, mineralogy, a live marine tank, and more. The artwork includes pieces by the Impressionists of the nearby art colony and sculptures by Auguste Rodin, Hiram Powers, Frederick MacMonnnies, and others.

This hilltop delight resides within Bruce Park, a public park with fascinating geological elements called gneiss outcrops. These metamorphic rock pieces jutting out of the ground were formed some 450 million years ago within the Earth’s crust. The park is a beautiful place to stroll by ponds with geese, ducks, and an occasional pair of swans. Spring flowers add color, while summer sees gorgeous rose gardens in bloom.

Greenwich Point Park in Connecticut.

Picnic At Greenwich Point Park (Tod’s Point)

Greenwich Point Park, known by locals as Tod’s Point, offers a gorgeous beach for swimming and sunbathing, hiking trails, bird-watching and wildlife viewing, paddleboarding, kayaking, canoe rentals, and incredible spots for picnicking. You can even look across the Long Island Sound to the New York City skyline. You can also enjoy fishing, boating, cycling, windsurfing, and more. Fill your cooler and basket to enjoy a picnic and relish the beauty of this 147-acre beachy wonderland.

The park charges non-residents a fee during peak tourism season (May through October) but not during the off-season, when it’s also beautiful.

Tour The Greenwich Historic Districts

Greenwich has a rich history, and architecture fans can experience much of it through the area’s built environment. Many of Greenwich’s historic communities are noted for their significant structures, residents, events, and landmarks. From Putnam Hill’s grand buildings to the working-class Historic Fourth Ward District, Greenwich’s historic districts include significant preservation efforts. Be sure to stop by Christ Church, featuring Tiffany stained glass windows, and Knapp’s Tavern, which once hosted George Washington.

The Greenwich Polo Club in Connecticut.

Experience The Sport Of Kings At The Greenwich Polo Club

The “sport of kings” is great fun, and there just aren’t that many places to watch a real live polo match anymore. Head to the Greenwich Polo Club and watch the horses and players compete in high-goal matches open to the public. Sundays are game days, and matches start at 3 p.m. Seating options range from lawn seating all the way up to grand cabanas for 50 guests. Food and drinks are available from caterers and gourmet food trucks, or you can bring a small picnic for yourself. A local favorite backcountry activity, a polo match makes for a memorable afternoon.

Look For Wildlife At The Greenwich Audubon Center

We enjoy hiking, bird-watching, wildlife viewing, exploring native wildflowers and plants, and supporting nature sanctuaries. So visiting the 258-acre Greenwich Audubon Center is one of our favorite things to do.

The Byram River flows through the main sanctuary, where you’ll find 7 miles of trails through forests, fields, lakes, streams, and stone homestead walls. Look for river otters, deer, coyotes, squirrels, wild turkeys, and other local critters. Plenty of birds like ducks and bluebirds make their home here, and you might just spy migrating birds like owls in the fall. For fun, pick up a letterbox activity sheet from the desk and see how many hidden boxes you can find along the trail.

The ferry in Greenwich.

Take A Ferry Ride

Diana lived in Greenwich for a time and so can offer a true insider tip. If you visit between June and September, take a ferry ride from the Arch Street Dock in Greenwich Harbor. You can take a “Cruise to Nowhere,” a peaceful 2-hour ferry tour of the Long Island Sound. Or stop at one of the two islands, the larger and more interesting being Great Captain Island with its granite lighthouse and wonderful walking trails.

Explore Old Greenwich

Greenwich’s backcountry is filled with mansions and sprawling estates owned by reclusive celebrities and hedge-fund billionaires. Another neighborhood worth exploring is Old Greenwich, the oldest established neighborhood in the area, dating to 1640 when the founding families bought the land from Native Americans. There’s a lot of history in this quiet and charming neighborhood -- one of America’s 100 richest places according to Bloomberg.

Explore the beautiful First Congregational Church, the Perrot Memorial Library, and Binney Park. Shop the boutiques along Sound Beach Avenue and grab a bite at the Beach House Cafe, Le Fat Poodle, or the Old Greenwich Social Club.

The Elm Street Oyster House in Greenwich.

Where To Eat In Greenwich

One of our favorite things about Greenwich is the abundance of delicious, authentic, and creative cuisine. Ethnic bites, modern culinary experiences, and hearty New England fare are all readily available.

Elm Street Oyster House

This incredible spot has received accolades for decades, and rightly so. In addition to the namesake oysters, Elm Street Oyster House has an excellent raw bar, fabulous seafood platters, and signature dishes to please every palate. Their extensive wine list makes it easy to pair outstanding food and beverages at this casual and welcoming local favorite.


You’ll find bold flavors in Greenwich restaurants. Nowhere is this more evident than in the Mediterranean cuisine at Douro, named for the home region of Chef Rui Correia. Located on Greenwich Avenue, the main downtown shopping and dining strip, Douro delights the taste buds with modern interpretations of Portuguese, Italian, Greek, and Middle Eastern dishes. From pitas and paella to piri-piri chicken and pasta, the food is as inviting as the inspiration from which it comes.

Meli-Melo Creperie

Meli-Melo Creperie is a Greenwich institution. This darling bistro and creperie is the perfect spot to refresh yourself with a delicious salad, freshly made soup, or specialty sandwich. Of course, if you’re a crepe fan, you will find much to love, from savory crepe classics with brie and herbs to sweet crepes with caramelized apples, chocolate sauce, and vanilla ice cream.

There are many other exceptional places for Italian, Chinese, Mediterranean, French, Greek, and classic New England food, especially along Greenwich Avenue.

Where To Shop In Greenwich

If you’re looking to spend an amazing day in historic Greenwich, Greenwich Avenue will provide you with more than enough to satisfy your craving for shopping.

Tiffany & Co. is a stunning store that will grab your attention with its unique clock and logo visible from the street. Other shops adorning Greenwich Avenue include Lynnens with luxury linens for the home, Petticoat Lane with ladies’ lingerie, Richards with apparel and more, and Michaelangelo of Greenwich with unique silver, crystal, and other gifts.

While you’re there, take a stroll and enjoy the incredible architecture of the Old Town Hall, Greenwich Post Office, Saint Mary’s Church, and Greenwich Town Commons.

The Stanton House Inn in Greenwich.

Where To Stay In Greenwich

Greenwich loves luxury, so it’s easy to find amazing places to stay during a visit.

The Delamar Greenwich Harbor Hotel is perfect for those who want amazing waterfront views plus attentive service in an elegant boutique.

The Hyatt Regency Greenwich stands as an impressive testament to old-world grandeur combined with modern amenities and comfort.

If you love modern decor and amenities, then The J House will please you, with iPads in every room, contemporary fine art, and poolside cabanas.

The Stanton House Inn provides a bit of classic New England romance in a charming bed and breakfast setting near downtown.

And, for a touch of Europe in Greenwich, consider the Homestead Inn-Thomas Henkelmann, which has won praise for its sophisticated architecture, design, and integrated art and artifacts.

It’s easy to spend an amazing day (or longer!) in historic Greenwich, where you can explore both the past and the present of this gorgeous and interesting New England town.

For more to see and do in Connecticut, visit this page.