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15 Towns Like Greenwich, Connecticut

A park beside the river at Towns Like Greenwich, Connecticut.

When you think of Greenwich, Connecticut, you may think of a beautiful New England town full of old money and extensively rich families. Both zip codes affiliated with the city are considered two of the richest in the entire country.

Not only are there heirs and wealthy families, but the local economy consists of manufacturing companies that deliver throughout the country and headquarters for many of these businesses. It does have the natural beauty of a suburb, however, offering large enough properties for private pools, tennis courts, and horseback riding for some.

Greenwich is not the only New England town that offers a slower-paced escape from a major city. Below are other cities like Greenwich, Connecticut. 

1. Stamford, Connecticut

Annual festival at Stamford, Connecticut.

While it is not one of the wealthiest zip codes like Greenwich, it is a popular Manhattan suburb just like Greenwich. Those who live in Stamford are often commute to Manhattan for work. There are at least 9 Fortune 500 companies that are in the town and contribute to the local economy. The biggest difference between Greenwich and Stamford, however, is the people who live there.

While the geography and beautiful New England views are the same, the demographics and social classes vary significantly. If you are planning to stay over in Stamford for the evening, expect to pay an average of $110 for the nightly rate. 

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2. New Canaan, Connecticut

A large yard for horses at New Canaan, Connecticut.

Found along the Connecticut Gold Coast, New Canaan is another beautiful New England town similar to Greenwich. With views and a resort feel, lots of rich tourists visit New Canaan as a summer getaway. While Greenwich was known for being rich and classical, New Canaan was gaining a reputation for the rich who wanted a modern take on their vacation homes and residences.

Born in agriculture and simple beginnings, New Canaan experienced a transition in the 20th century that made it a competing town with Greenwich. If you are planning to visit the area, expect a nightly rate average of $110, like Stamford.

3. Woodstock, Vermont

Cattles on the field on autumn at Woodstock, Vermont.

Picturesque, like Greenwich, Woodstock Vermont, is a small community in New England that has a slower pace compared to the rest of the state. There are a lot fewer residents than Greenwich, but it is a nice getaway location for those who work in a bigger city but need a more rural pace for the rest of their daily lives.

The historical Roseland Cottage is here and brings thousands of visitors to enjoy the historical architecture found throughout Woodstock. The average nightly rate for visiting Woodstock is approximately $130. 

4. Westport, Connecticut

Another Connecticut town with rich residents is Westport. The community has about half the population of Greenwich. but the residents and their lifestyles are similar to those in Greenwich. This city is also along the Long Island Sound, but not as easy a commute as Greenwich to Manhattan.

In the summer, many New England townies flock to the shore to take advantage of the warm weather. The average nightly rate for visiting Westport is $170 a night during the peak season. 

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5. Oak Bluffs, Massachusetts

Historical houses at Oak Bluffs, Massachusetts.

Located on Martha’s Vineyard Island, Oak Bluffs is a small New England town that historically attracted members of high society very much like Greenwich. This is a New England beach town, with homes that line the shore and make a great summer getaway for many New England families each year.

While it is small in size and population, those who visit are usually the same type of visitors who reside in Greenwich. If you plan to visit Oak Bluffs, expect to pay around $125 a night for a room or $200 for a beach house. 

6. Manchester, Vermont

Flowers in the front yard of a mansion at Manchester, Vermont.

If you wanted to pick up Greenwich and move it to Vermond, you would get Manchester. It is small in size and population, but the culture and visitors have the same interests. Those who want to escape the city for some quiet R&R for the weekend find Manchester to be the best place.

The properties are spacious and there is a lot of nature to enjoy when visiting the area. If you plan to visit Manchester for a night or two, you can expect to pay around $140 a night. 

7. Darien, Connecticut

Located close to Greenwich is Darien with a population of 22,000 residents and thousands of visitors each year. It is the smallest Connecticut town on the Gold Coast, but is full of families and family-oriented. Like Greenwich, those who live here commute to Manhattan for work, but find the town to be more accommodating and affordable.

There are public and private beaches available with ample amounts of golfing for residents and visitors. Expect to pay around $150 a night when you stay in Darien. 

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8. Bar Harbor, Maine

A view of Acadia Mountain National Park at Bar Harbor, Maine.

If you want a beautiful getaway at the entrance to the Acadia Mountain National Park, then you need to visit Bar Harbor, Maine. It has long been known as a vacation spot for New Englanders who want to escape their daily city lives and enjoy a slower pace. Like Greenwich, there is lots of dining, shopping, and entertainment available for visitors.

What is different, however, is the attraction to the outdoors. Whether you are having tea at Jordan’s Pond House in the National Park or enjoying a dinner cruise watching whales, it is a great escape. You can find decent lodging in Bar Harbor at $135 a night on average during the peak season. 

9. Cape Elizabeth, Maine

A small town with 2 lighthouses at Cape Elizabeth, Maine.

While it is on the other side of the New England states, Maine has a version of its own Greenwich, and that is Cape Elizabeth on the shore. The history of this township goes back to the 18th century. While cities grow around Cape Elizabeth, it has maintained its countryside, becoming a bit of a suburb of Portland, like Greenwich is of Manhattan.

The biggest difference between the towns, however, is the population size, where Greenwich is much larger. If you are planning to stay in Cape Elizabeth, expect an average rate of $170 a night. 

10. Weston, Massachusetts

While smaller than Greenwich with a 12,000 resident population, the demographics in race, wealth and industry are very much the same in Weston, Massachusetts. It is located just out of Boston, and has been home to a number of celebrities and hedgefund recipients for many years.

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It has that rural feeling, with lots of large homes on several acre properties. There is an attraction to this area for the history and art that surrounds the town. If you plan to stay in Weston, your average rate will be approximately $150 a night. 

11. New Castle, New Hampshire

Historical houses at New Castle, New Hampshire.

What began as a fishing village and humble beginnings, New Castle turned into a rich society escape very much as Greenwich did in Connecticut. History is rich in this culture also, with some homes surviving from the Colonial era despite environmental factors, wars, and natural disasters over the years.

Those who come to visit New Castle take a step back in time to enjoy the culture of fishing and catch up with politicians and socialites that are found along the sand. If you are planning to visit soon, your nightly rate will be between $130 to $155 a night, depending on the season. 

12. Newport, Rhode Island

One of the richest cities in New England, the mansions that reside in this city are some of the richest in the country. Those who have vacation homes or reside here year-round have some of the highest salaries in New England and are well-known in the community, like those in Greenwich.

Newport has been the site of several national sports openings and tournaments over the years. Sailing and fishing are big hobbies in the area for those who visit or live here. If you want to stay in Newport on your trip, expect to pay at least $200 a night. 

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13. Barrington, Rhode Island

Like Greenwich and Newport, there are a lot of rich and wealthy families residing in Barrington. It is also a suburb like Greenwich, where wealthy residents reside to get out of the city, but can easily access it when needed. Wealthy families who want some of the best schools in the country flock to Barrington because of the Blue Ribbon Schools in the town.

It is about a third of Greenwich’s population, but it does have that similar feel of elevated dining, arts, and entertainment appreciated by those with classical tastes. If you want to visit Barrington and experience the history of the town, you can get lodging for roughly $150 a night. 

14. Lexington, Massachusetts

Minute man statue at Lexington, Massachusetts.

With a population of 30,000, it is half of Greenwich, but the environment and culture are very similar. Lexington has more of a historical presence than Greenwich, attracting all types of visitors to the various museums, monuments, and beautiful parks that capture the essence of New England’s beauty.

Most of those who live in Lexington support the local community with their careers in Boston. It is just a few miles away, making it an easy suburb commute. It is known to be where the first shots of the American Revolution began, so the culture surrounding the city is rich and welcoming to guests.

If you are planning to give Lexington a visit soon, make sure you plan for $130 a night for quality lodging in the town. 

15. Wellesley, Massachusetts

A church and a small town at Wellesley, Massachusetts.With a reputation for being rich, like Greenwich, Wellesley is another town where most of the residents in the area are of higher tax brackets and deep wealth. The biggest difference between Wellesley and Greenwich, however, is the academic influence found at Wellesley.

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Since there are multiple colleges in the area, those who are wealthy and live in this area are also graduates of academia and have roots in these campuses. In addition, there is also a big influence of architecture in the shops and galleries that call Wellesley home.

You can find all types of entertainment during the day or night since the community has lots to offer the economy and they play as hard as they work. If you are planning to visit Wellesley during your New England trip, expect your nightly visit to be $160 each night.