New England’s Six Wealthiest Towns (And How They Got That Way)

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The wealthiest towns in each New England state all have good schools, beautiful homes and well-preserved historic districts. They are also, unsurprisingly, overwhelmingly white.

New England’s wealthiest towns also tend to produce and attract celebrities and highly accomplished people in the arts, sports and business. Some of their residents are hell-bent on keeping the wealthiest towns wealthy. Conservative provocateurs Glenn Beck and Ann Coulter live in New Canaan, Connecticut, and Grover Norquist lives in Weston, Mass.

The Wealthiest Towns Get Started

In many cases, the wealthiest towns started off as sparsely populated farm villages. Then after the railroad came and the Civil War ended, rich people started building country estates on them. Then the estates fell to the income tax and the Great Depression. So when World War II ended, real estate developers pounced on some of these rural enclaves and turned them into suburbs.

In two other cases — New Hampshire and Vermont — the wealthiest towns evolved from historic, well-preserved colonial villages.

Several different statistics can measure a town’s wealth, but we chose per capita income.

Here, then, are the wealthiest towns in each of the six New England states.

New Canaan, Conn.

Bet you thought it was Old Greenwich, right? But New Canaan has the highest per capita income, $99,016, in the wealthiest county in the wealthiest state in the union. Greenwich at $91,478 and Darien, at $94,376, came in as Connecticut’s second and third wealthiest towns, according to the Connecticut 2014-15 Adjusted Equalized Net Grand List per Capita.

New Canaan started out as a Congregationalist parish in 1731, and didn’t get incorporated until 1801. After the American Revolution, shoemaking took off in the town. Then in 1868, the railroad came to New Canaan, bringing wealthy New Yorkers looking for a country retreat. Lewis Lapham, founder of Texaco, built Waveny House and summered on the estate for many years.

The New Yorkers began to stay year-round, commuting to work in the city. In the 1890s, New Canaan earned the nickname ‘Next Station to Heaven,’ though detractors call it the ‘Next Station to Hell.’ In 1980, The Official Preppy Handbook listed New Canaan as one of the preppiest towns in America.

Like most of New England’s wealthiest towns, New Canaan has preserved some of its colonial buildings. But the town has an unusual concentration of mid-century modern homes, such as Philip Johnson’s Glass House. A group of modern architects known as the Harvard Five lived and worked in New Canaan, all followers of Bauhaus architect Walter Gropius.

Not everyone loved the modern homes. Of the 80 or so built between 1940 and 1960, about 20 have been torn down. The town now tries to preserve them. You can see many of them in the 1997 film The Ice Storm.

Rick Moody, who wrote The Ice Storm, lived in New Canaan. Today, the town’s 20,000-odd residents include quite a few show people, including Martin Mull, Paul Simon, Harry Connick, Jr., Mike Wallace and Brian Williams.

Cape Elizabeth, Maine

Cape Elizabeth actually has a lower per capita income than North Oxford, Maine. But North Oxford is technically an unorganized territory and had only 17 residents in 2000, so we’re sticking with the seaside town of Cape Elizabeth.

King Charles I renamed Cape Elizabeth after his sister, Elizabeth of Bohemia, when explorer John Smith brought him a list of North American places with  native names. Anglican traders and fisherman came to the frontier village, which for decades was embroiled in the French and Indian wars.

In 1765, Cape Elizabeth separated from Falmouth (now Portland).Then in 1895 South Portland separated from Cape Elizabeth. The two towns had diverged in character: Cape Elizabeth remained rural, while South Portland grew with commerce and industry. Then, following the typical pattern, wealthy industrialists found the pretty countryside near the city a perfect place to build their estates. And after World War II, Cape Elizabeth turned into an affluent suburb.

Per capita income in Cape Elizabeth, population about 9,000, was $57,725 in 2016.

You’ve seen pictures of Cape Elizabeth’s most famous landmark, Portland Head Light. The town also has a number of Shingle Style houses designed by John Calvin Stevens. Two film icons lived in town: director John Ford was born there and Bette Davis had a summer home in Cape Elizabeth.

Weston, Mass.

Ever wonder where all those athletes with the astronomical contracts go to live? Try Weston, Mass., the wealthiest town in Massachusetts.

Weston was little more than a field for grazing cattle until its incorporation as a town in 1712. Since the town lies along the Boston Post Road, taverns thrived serving travelers. Two still stand today as historic properties — along with one local historic district, 10 National Register districts, 26 historic areas, and seven houses listed on the National Register of Historic Places.

The railroad brought small factories to Weston, and then it brought business moguls who liked the quick train ride from Boston. They began building large estates on land unsuitable for farming.

In 1927, a wool tycoon built Henderson House, the last great summer estate in Weston. About a dozen more huge estates survive, and rich people are building new ones. Hedge fund manager Jim Pallotta in 2007 built a 27,000-square-foot mansion nicknamed ‘the house that ate Weston.’

Weston boomed after World War II. More than half of the town’s increasingly expensive houses were built between 1950 and 1979. By 2017 the population reached 11,389. Today the median home price is about $1.5 million and the per capita income $105,217.

Five of the 50 richest people in Massachusetts live in Weston, and so do some of New England’s most beloved sports heroes: Celtics M.L. Carr, John Havlicek and Robert Parish. Bruins legend Bobby Orr lives in Weston, as do two former Red Sox players, David Ortiz and Jerry Remy.

New Castle, N.H.

Tiny New Castle, a collection of island on New Hampshire’s seacoast, started out in 1623 as a fishing village. Within the next decade the British built a fort to protect the harbor. The state incorporated New Castle in 1683 and named it after the fort, now a historic landmark known as Fort Constitution.

For many years, the world overlooked the fishing village squeezed onto several small islands covering just .8 miles. That neglect preserved many of New Castle’s colonial-era homes. The town’s residents, 968 in 2010, have restored and preserved many of those houses.

In 1821, bridges connected New Castle to Portsmouth on the mainland. Then in 1874, the town got a huge boost with the construction of the grand hotel, Wentworth-By-The-Sea. The largest structure on New Hampshire’s 18-mile coast, it attracted famous socialites, politicians and business leaders from around the world. At the height of its glory, Wentworth-By-The-Sea accommodated negotiators for the Treaty of Portsmouth, which ended war between Japan and Russia in 1905.

Wentworth-By-The-Sea began to decline with the rise of the automobile, but New Castle’s fortunes continued to rise. Per capita income tops the state at $97,601, according to the 2011-2015 American Community Survey 5-year estimates.

Local preservationists saved Wentworth-By-The-Sea from the wrecking ball in 1997 by finding a new owner, Ocean Properties. By 2003, the restored hotel opened as a Marriott hotel property.

Barrington, R.I.

You’d probably guess Newport as the wealthiest town in Rhode Island because of its famous Gilded Age mansions. But you’d be wrong. Barrington, just southeast of Providence, actually has the highest per capita income in the state, according to the U.S. Census Bureau’s 2012-2016 American Community Survey 5-Year Estimates. Per capita income for Barrington was $59,464. Newport wasn’t even second. That honor belongs to Jamestown, just west of Newport.

Congregationalist Separatists founded Barrington in 1717, and for many years it remained a farm community. Then brickmaking companies moved into town, employing many French-Canadians and Italians. After World War II, the flight from the city began to transform Barrington into a bedroom suburb.

The population more than doubled between 1950 and 1960. In 2015, 16,240 people lived in Barrington. Spalding Gray, Sean Spicer and Roger Angell came from Barrington.

Like most of the wealthiest towns in New England, Barrington has preserved its history in nine historic districts and claims to have excellent schools.

Old Bennington, Vt.

Old Bennington, an incorporated village inside Bennington, is not only the wealthiest town in Vermont, it’s possibly the most historic.

In 2010, Old Bennington’s per capita income topped Vermont’s list at $40,884, putting it ahead of Manchester Village by $33. Only 139 people lived in Old Bennington that year, which means one wealthy resident could have skewed the per-capita income figures upward — or downward.

However, Old Bennington’s many large, expensively restored Revolutionary-era homes, suggest most Old Benningtonians are comfortably fixed.

New Hampshire Gov. Benning Wentworth chartered Bennington (and named it after himself) in 1749, making it one of the oldest as well as wealthiest towns in the state. Vermont law later created the incorporated village, a defined area within a town. Vermont’s incorporated villages can provide some municipal services like drinking water, sewer systems, police, fire, trash collection and building code enforcement.

Its historic district includes 93 buildings and objects, including the Battle of Bennington Monument and the Old First Church, named Vermont’s ‘colonial shrine’ by the Legislature. Robert Frost and his wife Elinor are buried behind the church, along with 75 Revolutionary War soldiers who died in the Battle of Bennington. A stone near the cemetery marks the spot where Ethan Allen’s house once stood.

Images: Glass House, By Staib – Own work, CC BY-SA 3.0, https://commons.wikimedia.org/w/index.php?curid=7797606; Peirce-Henderson House in Weston, By User:Magicpiano – Own work, CC BY-SA 4.0, https://commons.wikimedia.org/w/index.php?curid=15922502; Old First Church By Nheyob – Own work, CC BY-SA 3.0, https://commons.wikimedia.org/w/index.php?curid=16986574. Canaan Main Street By Jerry Dougherty – http://public.fotki.com/gcdougherty/all-towns-and-cities/north_canaan_ct/canaanvillagemainst-3.html, CC BY 2.5, https://commons.wikimedia.org/w/index.php?curid=74545267.

This story was updated in 2024.