New England's Preppiest Towns

And Villages. And Enclaves. All Photos by/of Muffy Aldrich.

All Photos by/of Muffy Aldrich

Criteria for What Makes a Town Preppy

What are the attributes that make for a preppy town? My list of criteria, in no particular order, include:

• Architecture and historic preservation;

  

  

• A proper town green;

• Level of civic participation (for both local businesses as well as charitable organizations);

• Private clubs;

• Private schools;

• Safety;

• European motor specialists;

• The percentage of land devoted to walking trails and preserved open space compared to playing fields;

  

  

  

• Congregational churches;

• Commuter train service;

• More station wagons than SUVs;

• More organic farms than high end restaurants;

• The percentage of houses that never go up for sale;

• The percentage of people whom you wouldn't know if they were very well off or living in genteel poverty;

• The percentage of locally owned shops versus chains;

• Quality of harbors and/or miles of coastline;

• The number of well-bred dogs being walked;

• Egalitarian spirit;

  

  

  

• Services for seniors;

• Percentage of people wearing some variation of The Uniform;

My List of New England Preppy Towns:

Connecticut

• Darien

• Guilford

• Guilford -Sachem's Head

• Easton

• Essex

  

  

  

• Fairfield - Greenfield Hill

• Fairfield - Mill River

• Farmington

• Fenwick

• Green's Farms

• Kent

• Lakeville

• Lyme

• Madison

• Mystic - Mason's Island

• New Canaan

  

  

  

• Nonquitt

• Old Greenwich

• Old Lyme

• Redding

• Rowayton

• Roxbury

• Salisbury

• Sharon

• Southport

• Stonington Borough

• Suffield Village

• Washington

  

  

  

• West Cornwall

• Weston

• Wilton

• Woodbury

Maine

• Camden

• Cape Elizabeth

• Castine

• Christmas Cove

• Kennebunk

• Kennebunkport

• Kittery

• Northeast Harbor

• Prouts Neck

• Rockport

• Seal Cove

• Yarmouth

• York Harbor

Massachusetts

• Andover

• Beverly Farms

• Chatham

  

  

  

• Chestnut Hill

• Cohasset

• Concord

• Cuttyhunk Island

• Deerfield

• Dover

• Duxbury

• Dunstable

  

  

  

• Edgartown

• Groton

• Hamilton

• Hingham

• Manchester/ Manchester-By-The-Sea=

• Marblehead

• Marion

• Nantucket

• Newburyport

• Orleans

  

  

  

• Rockport

• Salem/ McIntire District

• South Dartmouth/ Padanaram

• South Hadley

• Wellesley

• Wellfleet

• Wenham

• Westport/ Old Hill

• Weston

• Wianno/Osterville

  

  

  

• Woods Hole

New Hampshire

• Center Harbor

• Exeter

• Francestown

• Gilmanton

• Hancock

• Hanover

• Hopkinton

  

  

  

• New London

• Portsmouth

• Rye

• Wolfeboro

Rhode Island

• Barrington

• Bristol

• Jamestown

• Little Compton

• Narragansett

• Newport - Narragansett Bay

• Watch Hill

• Wickford