Greenwich Avenue: Everything You Need To Know | Stanton House Inn

Greenwich Ave, looking uphill to the intersection with East Putnam Avenue

Greenwich Avenue has a few names:


  • The Rodeo Drive of the East
  • Greenwich Ave
  • Or just “The Ave”, if you’re a local


But whatever you call it, this street is the center of all things Greenwich, Connecticut. Our main street hosts all types from traditional traffic cops to award-winning chefs. You’ll find waterfront hotels and bars, high-end stores, classic car collections. Plus, Greenwich art galleries with artists specializing in pop and contemporary styles.


The area offers a variety of dining options, from high-end to casual. It boasts specialty designer brands and fast fashion stores. And dining here is comparable to New York City, so lunch is a great way to keep the energy going. Or enjoy dinner as a capstone to a busy day exploring the Ave. It’s also the perfect place to just sit and watch people and luxury cars pass by.


Greenwich Avenue promises a unique blend of shopping, dining, and historic architecture. Trees lined the street, shading upscale boutiques and a diverse culinary scene. And more than a few architectural treasures befitting of a historic district.


Ready to discover the ultimate guide to Greenwich Avenue? Let’s get into it:


Quick hits

  • Take a step back in time on Greenwich Ave to witness its transformation from village to affluent suburb.
  • Explore architectural gems, unique boutiques and high-end retailers, international cuisine & waterfront dining.
  • Enjoy annual events like Art To The Avenue or take a stroll around the Historic District!

A Brief History of Greenwich Avenue

Postcard of Greenwich Ave in downtown Greenwich, looking south towards Railroad Avenue

Greenwich Avenue had a humble beginning as a cow path from the Boston Post Road down to the harbor. Now, it’s the main artery of a prosperous suburban community just outside New York City. That said, the transformation of downtown Greenwich didn’t happen overnight. It was largely thanks to locals like Henry O. Havemeyer and Robert M. Bruce. These philanthropists funded the development of public buildings such as the Havemeyer Building, a museum and a public school. And if you’re local, you’ll recognize their names for the buildings for which they paid.


Colonial Era

The journey began in 1640 when Europeans first settled Greenwich. By 1665, it formally incorporated as a Connecticut town. In 1703, locals divided town meetings between:




A “Town House” was built at the intersection of Putnam and Maple Avenue, down the street from our Greenwich, CT, bed and breakfast.



The town’s population boomed in the mid-19th century. It transformed from a farming village to a wealthy suburban community. The New Haven Railroad, which established a station at the lower part of Greenwich Avenue, was a major source of the boom. To avoid sounding too parochial to the Big City types visiting by train, Horseneck incorporated as the Borough of Greenwich in 1854.


The development of railroad and steamboat service allowed people to work in New York City while living here in downtown Greenwich. Wealthy New York capitalists like Henry O. Havemeyer and Robert M. Bruce donated lots of money to make their new home more like their hometown. Havemeyer donated money to construct the Havemeyer Building in 1892. Robert M. Bruce and his sister Sarah E. Bruce donated land for the construction of the Old Town Hall, now the Senior Center.


Early 1900s

Commercial development started to take place along the northern end of Greenwich Ave, near the Boston Post Road, in the 19th century. By 1882, the area had sidewalks, kerosene street lighting, and sewer and water lines. Commercial development continued into the 1920s, with the construction of grand buildings like the old Post Office. By then, the borough outshone the other Greenwich neighborhoods as the center of the town’s civic life. The last open lot on Greenwich Avenue was built on in 1947, now occupied by an office building for Fawcett Publications.


Greenwich Avenue Historic District

Clock on Greenwich Ave

Take a stroll through the Greenwich Avenue Historic District, and you’ll be stepping back in time. This district is a window into the 19th and early 20th-century commercial streetscapes of Connecticut, embodying an architectural diversity that’s delightful to explore. It’s a time capsule, with 152 buildings on the list, including:


  • Italianate structures of the late 19th century
  • Georgian Revival buildings of the early 20th century
  • Commercial style edifices that sprung up after World War I


Architectural Gems on Greenwich Avenue

Small park with war memorials in front of the former post office

Greenwich Avenue is a showcase of diverse architectural styles. The East End is home to historic buildings, including the Old Town Hall. Meanwhile, the Post Road vicinity features modern structures. Each building narrates a chapter of the area’s growth.


One notable example is the Greenwich Senior Center. This architectural marvel is listed on the National Register of Historic Places and is conveniently located near the former Post Office and the former Greenwich high school. Those buildings are now a Restoration Hardware and the town hall, respectively.


The Senior Center, designed in the Beaux Arts style, is an impressive example of the area’s architectural evolution. Construction was possible thanks to the generous patronage of Robert M. Bruce, a New York industrialist and philanthropist.


Greenwich Avenue Stores

Betteridge Jewelers storefront

When true shoppers think of shopping in Greenwich, CT, they think of Greenwich Ave. It offers a shopping experience that rivals Madison Avenue or SoHo. Here, you can find a mix of high-end retailers, independent designers, and unique local boutiques. Whether you’re in search of:


  • Apparel
  • Kids’ clothes
  • Jewelry
  • Home goods


You’ll find it here or on the side streets of the downtown Greenwich shopping district.

downtown greenwich shopping district map 1 Greenwich Avenue: Everything You Need to Know
Map design by Stanton House Inn using resources from

High-End Retailers


If luxury shopping is your thing, you’re in for a treat on Greenwich Ave. This street overflows with high-end retailers. You’ll find designer apparel, shoes, and jewelry that will make heads turn.


Some of the famous stores include


These establishments are known for their exquisite collections and exceptional customer service.


Unique Local Boutiques

Local boutique on Greenwich Avenue like Diane's Books

For those in pursuit of unique, one-of-a-kind items, Greenwich Avenue’s local boutiques are a trove. These boutiques offer an array of distinctive items, ranging from clothing, books, and accessories to gifts. Every visitor can leave with a special keepsake from their visit.


Among these boutiques, you’ll find unique stores like:


  • Diane’s Books
  • Petticoat Lane
  • Michelangelo’s silver store


Diane’s Books is one of the old-timers still holding on. It’s been a bastion of literature since 1990 in a world that’s moving digital. Michelangelo’s silver store is another. Established in 1979, it’s a monument to the enduring appeal of fine craftsmanship.


Some other nearby unique shops include:


  • Navy Lobster
  • Greenwich Exchange for Women’s Work
  • Sophia’s Costume Rentals


These unique CT shops deviate from the standard retail experience, contributing to the Ave’s unique charm.


Home Decor and Furnishings

Mirrors on a staircase at Restoration Hardware

Greenwich Ave is a paradise for high-end home decor and furnishings.


Stores like Restoration Hardware and Lynnens present a ton of options to elevate your living spaces.


You can discover everything from vintage treasures to contemporary pieces, providing ample inspiration for your next home makeover.


A local find here among the home decor shops is Patrick Mele.


Dining on Greenwich Avenue

Dining options on Greenwich Avenue, like the Ginger Man

After a day of exploring the unique boutiques and high-end retailers, you’re sure to be hungry.


No worries – the Ave has got you covered. It boasts a diverse range of dining options. Some of the best downtown Greenwich restaurants line the street.


You can find anything from international cuisine to casual eateries, and even waterfront dining.

map of the top restaurants in downtown Greenwich, CT, all within walking distance from Stanton House Inn
Map design by Stanton House Inn using resources from

International Cuisine

If you’re a foodie with an appreciation for global flavors, Greenwich Avenue restaurants are sure to satiate your cravings. Some of the options available include:


  • Italian cuisine
  • French cuisine, like Le Penguin on Lewis Street
  • Indian cuisine
  • Vegan options


Every meal at any of these restaurants is a culinary adventure.


Whether you’re drawn to the hearty Italian dishes at Terra Ristorante Italiano or you’re a fan of the refined French cuisine at Bistro V, an exciting culinary experience awaits you.


Waterfront Dining

L'Escale on Greenwich Harbor

For a truly memorable dining experience, try waterfront dining at L’Escale Restaurant. Situated right on the waterfront of Greenwich Harbor, this restaurant offers stunning views. The menu features a range of Mediterranean and French cuisine, including an exquisite lobster dish.


Casual Eateries and Cafés

If you fancy a quick snack or a coffee break, Greenwich Avenue has a variety of casual eateries and cafés. The Cottage, Méli-Mélo, and Grigg Street Pizza are some of the places that offer a relaxed setting. These are perfect spots for a leisurely lunch or a refreshing afternoon break.


Annual Events & Activities on Greenwich Avenue

Art gallery at the Greenwich Arts Council

Greenwich Avenue is not just about shopping and dining. It also plays host to a number of annual events and activities that add to its lively atmosphere.


Art to the Avenue

Every year in CT in May, Art to the Avenue transforms Greenwich Avenue into an expansive art gallery. During this event, local artists exhibit their work in various businesses along the avenue. It’s a vibrant display of the community’s creative talent.


Sidewalk Sales

If you’re a bargain hunter, the Sidewalk Sales are a must-visit during CT in July. Local retailers spill out onto the sidewalks offering sales, promotions, and activities. It’s a great chance to snag a deal while enjoying the avenue’s lively atmosphere.


Holiday Stroll

The Holiday Stroll is a festive event that lights up Greenwich Avenue over December in CT. With caroling, holiday lights, and a visit from Santa Claus, it’s a magical time sure to get you in the holiday spirit.


Staying in Downtown Greenwich near Greenwich Avenue

Charming lodging near Greenwich Avenue

If you’re planning to spend a few days exploring Greenwich Avenue and its surroundings, downtown Greenwich offers a few options for charming accommodations. Both provide comfortable lodging close to all the action.


Stanton House Inn

Stanton House Inn provides a unique stay in a beautifully restored 1840s mansion. It’s just a short walk from Greenwich Avenue, making it a convenient base for your exploration.


Delamar Greenwich Harbor

For modern luxury, Delamar Greenwich Harbor is an ideal choice. This hotel is located just a stone’s throw away from Greenwich Avenue. It boasts top-notch amenities including a spa and fitness center. Delamar Hotel also hosts L’Escale restaurant.


Directions to Greenwich Avenue from Stanton House Inn

Navigating from Stanton House Inn to Greenwich Avenue is easy. Simply take a right onto Maple Avenue, another right onto East Putnam Avenue (AKA Post Road) and you’ll be there in 0.3 miles. Then take a left onto Greenwich Avenue.


The simplest directions this innkeeper has given are:


The walk takes about 10-15 minutes, depending on how fast you’re walking. But what’s the point in rushing?


Discover more things to do in Greenwich, CT, near Greenwich Avenue

Statues in front of the Bruce

Greenwich Avenue should be just the beginning of your exploration. There are plenty more attractions, activities, and things to do in Greenwich, CT. A few nearby options include:


Bruce Museum

On a hill overlooking the Avenue and the harbor, the Bruce Museum is a hub for art, science, and natural history exhibits. It features carefully curated art exhibitions and engaging science displays. The museum provides a blend of education and entertainment that caters to all ages.


Greenwich Historical Society

The Greenwich Historical Society in Cos Cob, CT, offers a glimpse into the area’s past. It’s a great place to learn more about the region’s history and heritage.


Greenwich Point Park

For nature lovers, Greenwich Point Park is a must-visit. Whether you prefer hiking, swimming, or simply enjoying a picnic, this park offers a refreshing break from the city buzz.



Greenwich Avenue teems with history, architectural splendor, a luxury shopping scene, and plenty of dining options. It also hosts lively annual events. Nearby, you’ll find charming accommodations, and even more attractions to explore. It’s an ideal spot for a memorable getaway.


If you’re looking to embark on a shopping spree, a culinary adventure, or a historical exploration, Greenwich Avenue is the place to go. So, don’t delay! Start planning your trip to Greenwich Avenue and prepare yourself for a delightful visit!


Frequently Asked Questions


What is the main shopping street in Greenwich CT?

Experience the ‘Rodeo Drive of the East’ with a stroll down Greenwich Avenue. Locals refer to it simply as ‘The Avenue,’ and it is the main shopping street in Greenwich CT.


Is Greenwich walkable?

Greenwich is indeed a highly walkable town. Remember, it was established in a time before automobiles. So everything in downtown Greenwich is designed to be easily accessible on foot.


What are the richest parts of Greenwich?

Greenwich’s “Golden Triangle” holds the title as the wealthiest neighborhood in the nation. The most affluent areas in Greenwich are bounded by North Street to the East, Round Hill Road to the West, and the Merritt Parkway to the north.


What is Greenwich CT known for?

Greenwich, CT, is known for several things. It boasts the beautiful Greenwich Point Park, historic homes, and stunning gardens. The city is also a hub for the financial services sector. Additionally, it houses four charming beaches on Long Island Sound, offering excellent spots for swimming, boating, fishing, or just lounging on the sand.


What is Greenwich Avenue known for?

Greenwich Avenue is renowned for its shopping and dining, boasting prestigious stores such as Saks Fifth Avenue.


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