Guide to the Best Things to Do in Greenwich, CT

Known as one of the most luxe and historically rich coastal towns in Connecticut, Greenwich truly offers the perfect getaway for weekend warriors – located just a short train ride from New York City. Whether it’s a day trip escape or a weekend getaway, Greenwich is sure to delight travelers who want a memorable experience.

With its upscale boutiques and shops, an abundance of gourmet jaunts, and fine-dining romantic spots, Greenwich also offers cultural-historical sights, fabulous beaches and crowd-pleasing night-life (sipping craft cocktails while enjoying live music on Greenwich Avenue,) celebrity sightings (think Diana Ross, Ron Howard, NBA star Donovan Mitchell) – it’s truly the perfect getaway for Manhattanites looking to escape from the hustle-bustle of NYC to unwind and indulge in a town with a distinct style and relaxation. 

Short History Of Greenwich, CT

On July 18, 1640, Daniel Patrick and Robert Feake, settlers from Massachusetts, purchased the land between the Asamuck and Patomuck rivers in the area now known as Old Greenwich. For its first 16 years, Greenwich was a Dutch colony. But as the Dutch influence weakened, the Connecticut colony extended its jurisdiction into Greenwich and the town came under English control. 

For its first 200 years, the cultivation of farmland was Greenwich’s major enterprise. During the Revolutionary War, Greenwich was a garrison town and experienced numerous raids by the British army that destroyed many homes, crops, and took a large toll on human life. The arrival of the New York and New Haven Railroad in 1848 began the transformation of Greenwich into a residential community that it is today. During this time, many wealthy New Yorkers started building summer homes in the area. The town began to grow rapidly and land values began to rise. By 1928, Greenwich led the nation in per capita wealth. 

Today, Greenwich is an affluent suburb with many distinct, historic neighborhoods, abundant with plenty of fun-filled activities and cultural attractions to keep visitors engaged and entertained.

Things to do in Greenwich CT

Here are some of the top attractions in Greenwich, home to the famous Delamar Greenwich Harbor hotel and spa.  

The Bush-Holley House

This colonial house was originally built from 1728-1730 as a two-story structure overlooking the Cos Cob Harbor. At the turn of the 20th century, it became home to the Cos Cob Art Colony and the bedrock of American Impressionism. Among the early members were Childe Hassam, Ernest Lawson, Theodore Robinson, John Henry Twachtman, and J. Alden Weir.

The house is now the home of the Greenwich Historical Society and holds many important examples of American Impressionist works. The exhibits focus on the art and artists of the Cos Cob art colony, and aspects of Greenwich history. 

The Bruce Museum in Greenwich, Connecticut

The Bruce Museum

Located in downtown Greenwich (just a short walk from Delamar Greenwich Harbor), this museum serves as both an art and natural history exhibition space. The museum hosts 15,000 art pieces in permanent installations and several rotating exhibitions related to anthropology, natural history, decorative art, and fine art.

Visit Old Greenwich

There’s more to Old Greenwich than Greenwich Point. Old Greenwich occupies the southeastern edge of the town of Greenwich, bordering Stamford and extending into breathtaking views of Long Island Sound. With a New England-beach-town feel, this quaint coastal town is home to charming shops,  restaurants, and fun-filled activities, as well as the perfect spot to view the New York City skyline.  

The heart of Old Greenwich is its business district on Sound Beach Avenue. Rows of perfectly lined shops and restaurants line this walker-friendly street with benches for sitting, and plenty of colorful flowerpots. Visitors can dine at critically acclaimed restaurants like Le Fat Poodle, and Lugano Wine Bar & Salumeria, and shop at independently owned boutiques with some of the greatest finds from around the world. Check out Lily Shoes for the chicest shoes and bags from Europe. The area also has a train station that is listed on the National Register of Historic Places. 

Town of Greenwich, Connecticut

Greenwich Point Park

At the end of the commercial center of Old Greenwich is Greenwich Point Park, a stunning beach and 147-acre park that extends into the Sound. Visitors can enjoy amazing views of New York City’s skyline, as well as activities including jogging, walking, cycling, nature study, boating, fishing, sailboating, sunbathing, swimming, and picnicking.

Mianus River State Park

Nestled between Greenwich and Stamford, this 400-acre urban forest is named after the 20-mile river that flows through it and features forests, wetlands, rock formations, and gardens waiting to be explored.  Active visitors to the park can enjoy biking, fishing, hiking, and horseback riding. 

Putnam Cottage

Known as Knapp Tavern during the American Revolution, the bright red house on Boston Post Road hosted several troops and generals during the American Revolutionary War, including General Israel Putnam and General George Washington. The cottage became associated with Revolutionary War General Israel Putnam as it was supposedly the site of his daring ride down a steep slope, now known as Put’s Hill, with the British army in pursuit. This historic scene is even depicted on the seal of the Town of Greenwich. Today, the cottage serves as a museum and offers tours for those interested in learning the history of the American Revolution.

Shopping in Downtown Greenwich

Full of upscale boutiques such as Richard’s, and four Saks Fifth Avenue shops, including Barney’s at Saks, Saks Greenwich 10022-Shoe, and Saks Greenwich the Vault offering contemporary wear, high fashion, jewelry and shoes, local galleries and go-to designer shops, Greenwich has much to offer for residents and visitors alike. The historic Greenwich Avenue consists of shops and restaurants that are burrowed in buildings old and new. Some of the many shops and restaurants include Tiffany & Co., Hermès,, Out of the Box, Intermix, Zara and Rag & Bone. 

Book Your Weekend Getaway at Delamar Greenwich Harbor

Enjoy the coziest beds in our decadent guest rooms, indulge in the freshest shrimp cocktail and a glass of rose wine while enjoying breathtaking views of the Long Island Sound, and relax and rejuvenate at our award-winning spa at  Delamar Greenwich Harbor – the perfect boutique hotel to spend your weekend getaway in Greenwich. 

L’escale, our Mediterranean–inspired restaurant, has a waterfront view right on the harbor in Greenwich. Our Executive Chef, Frederic Kieffer, grew up outside of Paris and brings his exquisite French cuisine to the Connecticut table in true decadence. Reserve your spot to enjoy our ultimate IonixLight facial or enjoy our luxe couple massage at our award-winning spa featuring Biologique Recherche and Valmont products. Did we mention that Delamar’s pet policy allows for pooch companions under 100 pounds to room with you in the hotel? 

Book your weekend stay with us today and enjoy the best that Greenwich has to offer with the exceptional accommodations you won’t want to leave.