Photo by Salt Water New England

Friday, March 20, 2015

Preppy New England Towns

What are classic/preppy New England towns?


What are the attributes that make for a classic town?    Many people cite traditional criteria such as architecture and historic preservation; level of civic participation (for both local businesses as well as charitable organizations); private clubs; private schools; safety; and of course, European motor specialists.

What are the differences between simply a well-heeled town and a "preppy" town? How do these two categories overlap?  Where don't they?

How important is the percentage of land devoted to walking trails and preserved open space compared to playing fields?  Commuter train service? Are there more SUVs or station wagons?   Are there more nail and hair salons or more marine supply stores and tack shops?  Are there more high end restaurants or organic farms and farmers markets?  (And the incredibly high number of liquor stores in my town growing up did not go unnoticed as well as the number of well patronized watering holes.)  Are there more houses that are on the market every five years or properties that rarely go up for sale?   What is the percentage of genteel poverty (or what looks like genteel poverty) compared to the new high earners from away and all that they bring with them?   Which houses are tear-downs (are they the falling apart development houses or the old wood shingled structures by the water that aren't big enough)? What about locally owned shops versus chains? Oxfords and khakis compared to Under Armour? Quality of harbors and/or miles of coastline? Services for seniors?

Does the town have a productive hum, drawing people in, or is it either inert on one hand or overheated and sharp-elbowed on the other?  Should the availability of parking spaces or prevalence of tailgating be used as indicators?

Are there towns that used to qualify but don't anymore? What about the Black Dog towns?

And how does one think about the private enclaves, such as Prouts Neck, Fenwick, Nonquitt or smaller ones like Buffalo Bay and island communities like Islesboro, Fishers or the Thimbles?

New England Preppy Towns

  • Darien??
  • Guilford
  • Guilford -Sachem's Head.
  • Easton
  • Essex.
  • Fairfield - Greenfield Hill
  • Fairfield - Mill River
  • Farmington
  • Glastonbury
  • Kent
  • Lakeville 
  • Lyme
  • Madison
  • Mystic
  • Mystic - Mason's Island
  • New Canaan??
  • Noank
  • Old Greenwich?
  • Old Lyme
  • Redding.
  • Rowayton.
  • Roxbury
  • Salisbury
  • Sharon.
  • Southport?
  • Stonington
  • Stonington Borough
  • Washington
  • West Cornwall.
  • Weston?
  • Wilton??
  • Woodbury.
  • Camden.
  • Cape Elizabeth.
  • Castine
  • Christmas Cove.
  • Kennebunkport
  • Kittery
  • Northeast Harbor.
  • Oqunquit
  • Rockport 
  • Seal Cove.
  • South Bristol
  • Southwest Harbor
  • Andover
  • Beverly Farms.
  • Chatham?
  • Chestnut Hill??
  • Cohasset
  • Concord  
  • Cuttyhunk Island.
  • Deerfield
  • Dover.  
  • Duxbury 
  • Dunstable
  • Hamilton.
  • Harvard
  • Hingham
  • Manchester/ Manchester-By-The-Sea.
  • Longmeadow
  • Marblehead
  • Marion.
  • Nantucket
  • Newburyport
  • Rockport 
  • South Dartmouth/Padanarum.
  • South Hadley 
  • Stockbridge
  • Wellesley?
  • Wenham. 
  • Weston??
  • Williamstown
  • Winchester
  • Woods Hole
New Hampshire
  • Dover
  • Francestown
  • Gilmanton
  • Hanover
  • Hopkinton
  • Portsmouth 
  • Rye 
New York (why not...)
  • Bedford
  • Bedford Hills.
  • Bronxville?
  • Chappaqua?
  • Clayton
  • Cooperstown 
  • Fishers Island
  • Katonah 
  • Larchmont?
  • Locust Valley
  • Manhasset
  • Millbrook
  • Oyster Bay
  • Pound Ridge
  • Quogue
  • Rye 
  • Stony Brook
Rhode Island
  • Barrington.
  • Bristol?
  • Jamestown 
  • Little Compton.
  • Narragansett
  • Watch Hill
  • Wickford 
  • Brattleboro
  • Burlington?
  • Charlotte
  • Grafton?
  • Manchester 
  • Middlebury
  • Newfane?
  • Norwich?
  • Putney
  • Shelburne
  • Stowe
  • Waitsfield
  • Woodstock? 
? - On the fence

Sidebar Poll: What is the preppiest New England state?

Is it:
  • New York suburb Connecticut?
  • Fiercely independent Maine?
  • A previous title holder Massachusetts?
  • Rough and tumble New Hampshire?
  • Former costume jewelry capital Rhode Island?
  • Land locked but bucolic Vermont?


I grew up in NYC and spent my weekends and summers in Shoreline CT, and I enjoyed all the preppiness I could desire: tennis, sailing, beach clubs, dress codes, I could go on. Parts of the state have become bedroom communities for NYC commuters, but my vote is still for CT.
Walk around Fairfield County for a bit and you will see classic cars, Rovers, Nantucket Reds embroidered with martinis, and locals bringing their dogs into retail stores where they are met with warm smiles and hugs! Unfortunately their are also a lot of nasty people who are often new money and stressed to the max because they cant keep up financially, and feel the need to look down on others because a little money in their pockets. Highly un-preppy!
Preppy is more of a southern New England construct, so its either Mass or Conn. I've always thought of northern New England as more "Yankee" than prep. And parts of NY and NJ are most certainly preppy, despite what residents of the Hub may think.
As a Connecticut local and a Trinity grad, I must cast my vote for the nutmeg state. That said, I personally don't like our categorization as a New York suburb. I don't find Fairfield County to be preppy at all, it's far too glitzy/yuppy. The true Connecticut prep lies within Litchfield and Hartford counties, where the majority of the prep schools lie.

As a Mainah, born and bred, it ain't Maine. There are probably more descendants of the Winthrop Fleet living here than in any other state, but the "Preppy" lifestyle of BMW's and $500 B'rbour coats is for the summah people. I think Maine is the most "New-England-y" state in the Union. 

My vote has to be for the Commonwealth: Boston, Cambridge, parts of the Cape, Nantucket, Vineyard, South Coast, North Shore, South Shore. Hard to beat the entire package, 
Massachusetts girls = Uggs, yoga pants and a tightly gripped dunkin's coffee. Unfortunately it's no longer cool to be preppy in Mass. 
Middlesex. My alma mater. Peabody House immediately brings to mind two very different stories. One, as if from the Lord of the Flies, and the other is something out of P.G. Wodehouse. 

New Hampshire
Easy answer. New Hampshire. Why? Saint Paul's School. 'Nuf said. 

Rhode Island
The preppiest places in CT and MA are the deep rooted communities that go back generations. In contrast, the preppiest places in RI are places that draw outsiders from far away. Newport is at its best hosting international patrons, and at its worst when overrun by over dressed tourists from Cranston and Woonsocket. 

I remember when a Vermont neighbor down the road complained that the temporary postal delivery man had left her mail in the wrong spot, citing that “these Vermont peasants” can’t get anything right.   The delivery man, a friend of mine, was a graduate of Governor Dummer Academy and Brown University, his wife’s family having arrived in Massachusetts on the Winthrop fleet. “Up here”, my friend told me with a chuckle, “you never know who might be delivering your mail.”  
I have to give my vote to Vermont. While technically landlocked, Vermont offers a variety of landscapes including lush farming valleys, the snowy Green Mountains, and our once upon a time ocean, Lake Champlain. 

Final Results:

The most preppy states in New England:

  1. Connecticut: 51%
  2. Massachusetts: 27%
  3. Maine: 11%

The least preppy states in New England:

  • Rhode Island: 4%
  • New Hampshire: 2%
  • Vermont: 2%

Pictures from Salt Water New England

Here are quite a few pictures from our archives representing five of the New England states.  (Apologies to Vermont.)