Downtown Greenwich, CT: Top Guide to the Absolute Best Here [+Free Map]

I am proud to say that I was born and raised in downtown Greenwich, CT.

Greenwich is one of the largest municipalities in Connecticut, and the largest that still calls itself a town. That said, it does still have a small town feel to it.

Each neighborhood in Greenwich has its own unique character, actually. And downtown Greenwich is no different.

Greenwich is typically known for being lily-white and having a high average income. Yet downtown Greenwich is much more diverse than non-locals realize.

For such a small town, downtown Greenwich punches above its weight class culturally, with plenty to keep you busy exploring for a long weekend. An added plus is that everything in downtown Greenwich is walkable. That’s obviously fitting for a town settled long before automobiles existed.

Watch our video, below, for a quick intro to the downtown neighborhood of Greenwich CT. And be sure to keep scrolling for the full guide, and a map of our charming little town center!

Map design by Stanton House Inn using resources from Flaticon.com

A Brief History of the Greenwich Business District

Downtown Greenwich wasn’t always the main business district in town.

Before the arrival of the railroad, Cos Cob was busier. With roads in western Connecticut as poor as they were, Cos Cob’s port on the Mianus River was an easy way to transport goods and people to and from New York City.

The borough of Greenwich was the name for downtown Greenwich within what was then called the town of Horseneck. Back then, it was more of the spiritual and administrative center of town.

In fact, the original town hall was built right at the corner of Maple Avenue and East Putnam Avenue. There’s no mention, but it was built where the Civil War memorial stands today in front of Second Congregational Church.

Upon completion of the railroad line from NYC to New Haven in the mid-1800s, the town changed its name from the parochial “Horseneck” to Greenwich.

Since then, downtown Greenwich around Greenwich Ave took off. Wealthy New Yorkers built second homes close to town so they could easily and quickly escape Manhattan to their country estates.

Once the automobile became the preferred mode of transportation in the mid-1900s, downtown Greenwich went into decline. Anyone who could afford to lived in Backcountry Greenwich.

But that meant that downtown Greenwich real estate stayed relatively inexpensive. As such, it was where many lower to middle class citizens lived in town.

Modern Era

Today, now that living in central locations is back in style, rents and real estate prices are on the rise. And the makeup of downtown Greenwich has changed to match that.

Greenwich Avenue storefronts, where rents are highest, are full of businesses that can afford the high cost:

High-end restaurants
National high-end chain stores
Banks
Spas and salons

But the many side streets of downtown Greenwich have plenty of local shops, boutiques, and eateries worth exploring.

The Best Things to Do in Downtown Greenwich

As I mentioned before, I have grown-up in downtown Greenwich in the building that is now Stanton House Inn. So, my recommendations are all based-off of distance from my childhood home.

We are the only downtown Greenwich bed and breakfast inn, by the way.

The Greenwich Design District

Centered around the Post Road (an older name for East Putnam Avenue), the Greenwich Design District is a recent moniker for the area. But considering how many interior design, art galleries, and floral shops are in the area, the name seems to make sense.

With such retailers as:

Among the 18 different stores and shops, the Greenwich Design District is already known as a one-stop shop for home design. Now it has a fancy name to go with it.

Art Galleries in Downtown Greenwich

For the artistic or aficionado, wandering through the art galleries of downtown Greenwich fits with visiting interior design stores.

And there are plenty to choose from, sprinkled throughout downtown Greenwich. A few top ones include both free galleries and ones selling the art on their walls:

Downtown Greenwich Shopping

Downtown Greenwich is most well known as the Greenwich, CT, shopping district.

Greenwich Avenue, at the center of that shopping district, is full of luxury brands you can find elsewhere:

But there are still plenty of unique local finds, both on and near Greenwich Avenue.

Some local stores still on Greenwich Avenue include:

Vineyard Vines (the flagship store, which started here in Greenwich)
Betteridge Jewelers (also started here in Greenwich)
Out of the Box
Richards
Oggi 5 Boutique
Black Petunia
Manfredi Jewels
Shreve, Crump & Lowe

And a few great finds for shoppers in downtown Greenwich not on Greenwich Avenue include:

And the consignment shops and thrift stores of downtown Greenwich deserve their own list:

Downtown Greenwich Restaurants

Greenwich Avenue was once home to only a few old, family-owned restaurants. It has experienced an explosion of new restaurants in the past few decades.

Now, Downtown Greenwich is a culinary destination in and of itself. Everything from Italian to French to Indian makes an appearance on a list of downtown Greenwich restaurants.

Greenwich Avenue Restaurants

There are plenty of options on Greenwich Avenue alone to satisfy a wide variety of palettes.

Just a few options along Greenwich Avenue, from top to bottom (or closest to us to farthest away) include:

The Granola Bar, a hip breakfast and brunch spot
Pasta Vera, a simple Italian eatery
The Ginger Man, a classic New England tavern
Terra Ristorante Italiano, offering upscale Tuscan cuisine
Bistro Versailles, a French bakery and bistro
Meli-Melo Creperie, a French cafe
Mediterraneo, a seafood-heavy Mediterranean menu with a seasonal patio
Steam, a Chinese restaurant with a cute seating area
Putnam Diner, a classic New England diner
Eastend, for stylish New American fare

More Greenwich Restaurants not on Greenwich Avenue

But Greenwich Avenue is not where the restaurant scene ends in downtown Greenwich.

Within a few blocks of Greenwich Avenue sit, from closest to Stanton House Inn to farthest away:

Stanton House Inn’s Tea Room
Coffee for Good, a not-for-profit coffeeshop with an awesome purpose, and only a 2-minute walk from us
Asiana Cafe
Townhouse
The Spread
Blackstones Steakhouse
Le Penguin
Kira Sushi
Elm Street Oyster House
Doppio
Myx Kitchen
MacDuff’s
Thai Basil
L’Escale, the only waterfront dining option in downtown Greenwich

Downtown Greenwich Attractions and Points of Interest

Greenwich, Connecticut, has eleven historic districts. Of those, five are in downtown Greenwich:

Putnam Hill Historic District
Fourth Ward Historic District
Greenwich Avenue Historic District
Greenwich Municipal Center Historic District
Greenwich Memorial Hospital Historic District

And all are within walking distance of each other, if you want to plan an afternoon walking tour, one of the best free activities in Connecticut.

And within and near those historic Connecticut districts include many points of interest special to Greenwich history.

In many ways, these churches, muncipal buildings, and others are special in being emblematic of the region’s history in general.

Major Downtown Greenwich Points of Interest

Downtown Greenwich has plenty to keep a visitor busy. Most Greenwich museums are either downtown or close by, for example.

Everything on this list is within walking distance of each other, though some would be a longer walk than others. And downtown Greenwich slopes from an inland ridge on which many of the town’s churches and Stanton House Inn sit down to the Long Island Sound coast.

Fortunately, if you’re not feeling walking up hills, it’s easy to order a Lyft, Uber, or Greenwich Taxi.

Putnam Cottage

Putnam Cottage was also known as Knapp’s Tavern during the American Revolution. It was first constructed in the 1600s and used as a tavern. As the official name implies, it housed General Putnam during the War. He fled from the British from here on his locally-famous escape over what’s now known as Putnam Hill. Knapp’s Tavern even hosted General George Washington and his entourage for lunch during the War.

Today, Putnam Cottage is open for tours hosted by the local Daughters of the American Revolution chapter. That said, it’s only open certain Sundays in the warmer months.

Greenwich Senior Center (also known as the Old Town Hall)

The Greenwich Senior Center is located across the street from the Greenwich Town Commons at 299 Greenwich Avenue.

The building, designed by Mowbray and Uffinger in the Beaux Arts style, was built in 1904 to serve as Greenwich Town Hall. The structure is shaped like a vertical cube and has three stories, the first of which is rusticated. There is a clock beneath the domed cupola, rising above a copper cornice. Robert M. Bruce, another New York philanthropist, built the structure. Upon its completion in 1905, he donated the building to the town. The structure is listed on the National Register of Historic Places.

Havemeyer Building

This structure, located at 290 Greenwich Avenue, was the first constructed in the Greenwich Municipal Center Historic District. Loring & Phipps designed it, and it has a Richardsonian Romanesque design with a pronounced horizontality, accented by several architectural elements. The Syrian arch surrounding the recessed entrance and the elliptical-arched loggia in front of the auditorium wing are two impressive examples. The Havemeyer School was built in 1892 by New York philanthropist Henry O. Havemeyer for use as a public school.

Today, it is the home of the town’s Board of Education department.

Two war memorials stand in front of the building: one for World War II and the Korean War (built in 1956), and another for Col. Raynal Bolling (built in 1921).

The building used to be across the Havemeyer Fields from Greenwich High School, though that building on Field Point Road is now the town hall.

Bruce Museum

What was once a private mansion overlooking Greenwich Harbor is now a globally-recognized destination.

The Bruce Museum includes a permanent exhibit devoted to the local biome and natural history of the area. But it also hosts regularly rotating art exhibits. Some exhibitions don’t typically leave their home countries, but make their way to Greenwich and the Bruce Museum.

The Museum is also rolling-out a major, multi-million dollar expansion to make it even more of a world-class destination.

Bush-Holley House & Greenwich Historical Society

While not officially in downtown Greenwich, the Bush-Holley House is so close it’s worth mentioning.

The Bush-Holley House is located on the Strickland Road Historic District in Cos Cob. It is the only building in Greenwich registered as a National Historic Landmark. Like Stanton House Inn, the Bush-Holley House and surrounding property has lived a lot of different lives:

Farmhouse home overlooking Cos Cob harbor
Mill
Post office
Boarding house
Impressionist artists colony

And today is a museum and meeting space. Recent additions to the facilities include:

A gallery of art produced on site by artists that used the Bush-Holley House as a retreat from New York City
A refurbishment of the Bush-Holley house back to two major periods of the house: Revolutionary War period and late 1800s. One of the more interesting features is an attic recreated to match when enslaved adults and children lived there

Downtown Greenwich Churches

Several of the churches in downtown Greenwich have been central to life here for centuries. While many are experiencing declines in attendance, they are still impressive to see, both inside and out.

Close to Stanton House Inn in the Putnam Hill Historic District are Second Congregational Church and Christ Church

Still close-by is the First United Methodist Church. It was originally built as a country church and now looks out of place in the middle of a busy commercial district.

On or close to Greenwich Avenue are the First Presbyterian Church and Saint Mary’s Church. Both have beautiful interiors.

Parks in Downtown Greenwich

At the turn of the 1900s, Greenwich was smart enough to maintain plenty of its green space as it changed from a rural community to a major Connecticut town.

Bruce Park
To the east of the Bruce Museum, Bruce Park is what’s left of the Bruce estate. While part of Bruce Park was commandeered to build Interstate 95, what remains is still serene. The park was designed as a managed, bucolic wilderness, like Manhattan’s Central Park. Take a stroll at Bruce Park on weekdays and you’ll see plenty of Greenwich office workers enjoying the sun while eating lunch on one of the many picnic benches.
Roger Sherman Baldwin Park
Situated next to Greenwich Harbor, Roger Sherman Baldwin Park offers commanding views of the water. It also features outdoor events, including summer concerts.
Island Beach
This is not in the neighborhood, per se. Instead, it’s just off the coast, and accessible only by ferry. But it’s the closest beach to the center of town.
Greenwich Town Common
The center of the Greenwich Municipal Historic District on Greenwich Avenue, the Greenwich Town Common was where local farmers kept livestock. Hence the “Common” name. Today, it’s flanked by historic and modern municipal buildings:

The Senior Center
Historic Post Office (now a Restoration Hardware)
Today’s Town Hall (formerly the High School)
The Board of Education building

Greenwich Hospital
A local institution since the early 1900s, Greenwich Hospital has come a long way from its early, country clinic, days. Today, Greenwich Hospital is one of the top facilities in Connecticut.

Downtown Greenwich, CT, Real Estate and Living Here

More than a few people visit downtown Greenwich and decide to make the move here.

Even locals are selling their more expansive Greenwich mansions and moving closer to town.

And it’s easy to see why: walkable, with plenty to do in such a relatively small town. I donated my car shortly before moving back to Greenwich and haven’t missed it since.

Besides everything above, there is a fantastic library, pet and hardware stores, and several grocery stores:

Whole Foods (a 10-minute walk from us)
Stop & Shop (a 5-minute drive from us)
Acme Grocery Store (same distance)

For the right price, there are plenty of apartments, condos, mansions, and homes to buy or rent. Read our guide to the Greenwich, Connecticut, real estate market for more information.

Lodging in Downtown Greenwich, CT

You’ll find accommodations that mix modern comfort and historic charm in downtown Greenwich. This lovely town has beautiful streets with great places to shop, eat, and stay. In downtown Greenwich, you have two great choices: Stanton House Inn and Delamar Greenwich Harbor. They both offer a unique stay. And that goes for even if you’re looking for pet friendly hotels in Greenwich, CT.

Stanton House Inn

Our mansion bed and breakfast is full of history and turn of the century charm. Guests can experience the past while enjoying modern comforts. This charming bed and breakfast, dating back to 1843, exudes the essence of classic elegance. The peaceful oasis has beautiful buildings and gardens, while still near to it all. The inn is within walking distance of the shops, restaurants, and art galleries on Greenwich Avenue. Stanton House Inn is a great place for relaxing while staying close to our town’s cultural scene. And we’re a dog-friendly bed and breakfast, as an added plus for those interested.

Delamar Greenwich Harbor

The Delamar Greenwich Harbor is a luxury Greenwich hotel with modern amenities. It offers beautiful views of the harbor. The rooms are nicely furnished and some have beautiful views of the harbor, creating a peaceful retreat. The hotel is in a great location near downtown. The Delamar Greenwich Harbor is located by the water and has top-notch amenities. It provides a perfect mix of relaxation and luxury in downtown Greenwich.

Download a Free Copy of the Official Downtown Greenwich, CT, Map

I bet you didn’t think there was so much to do in such a small town.

Keep track of everything there is to do here when you download a free copy of the downtown Greenwich, CT, map.

Updated and republished: June 26, 2023

The Best of Downtown Greenwich, CT: The Ultimate Guide