Photo by Salt Water New England

Tuesday, January 28, 2020

New England Preppy Towns

Photos by Salt Water New England

New England Preppy Towns*

  • Darien
  • Guilford
  • Guilford -Sachem's Head.
  • Easton
  • Essex.
  • Fairfield - Greenfield Hill
  • Fairfield - Mill River
  • Farmington
  • Fenwick
  • 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
  • Camden.
  • Cape Elizabeth.
  • Castine
  • Christmas Cove
  • Kennebunk 
  • Kennebunkport
  • Kittery
  • Northeast Harbor.
  • Prouts Neck
  • Rockport 
  • Seal Cove.
  • Yarmouth
  • York Harbor 
  • 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 
  • South Dartmouth/ Padanaram.
  • South Hadley 
  • Wellesley
  • Wenham. 
  • 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
  • Watch Hill
  • Wickford 
Vermont (Arguably none, but perhaps...)
  • Brattleboro
  • Burlington
  • Charlotte
  • Grafton
  • Manchester 
  • Middlebury
  • Newfane
  • Norwich
  • Putney
  • Shelburne
  • Stowe
  • Waitsfield
  • Woodstock 


  1. Curious, why are there arguably no “preppy” towns in VT? I admittedly haven’t seen much of the state.

  2. My question, too. No coastline?

  3. Westport, CT should be on the re, IMO.

  4. Not that I have anything against Vermont, but Donald Hall wrote a very amusing essay called 'Reasons for Hating Vermont'. It's one of many thoughtful, funny, and often elegiac essays about being a New Englander in his book, 'On Eagle Pond'.

    1. Don Hall knew his way around New England. Thanks to his New Haven area childhood and adolescence he appreciated a good “apizza.” If you read his “Essays after Eighty” you will learn he had trouble, even in Italy, finding a pie that met New Haven standards. Alas, it’s also very unlikely he would have been satisfied with a pizza served in any town on this list.

    2. Mr. Hall might’ve approved of Bufalina in Guilford, Conn. Their pizza, while a little touchy-feely and not New Haven style, is tasty. Folino’s, the original in Shelburne Vermont, had it going for a while. They opened under the guidance of a New Haven native. The pizzas were baked in ovens warmed to 700+ degrees. The sauce had tang. Toppings were select. But the crust is now more soft and dough-y than it ought to be. Worth a try though, if you’re in the area.

  5. Prouts Neck isn't a town--it's in the town of Scarborough. :)

  6. Amherst didn't make the cut, huh? It's the only town in New England I've ever lived in.

    1. But South Hadley did? I'm chuckling.

  7. Superb! Thanks so very much!

  8. A minister that I know was transferred from West Virginia to New Hampshire and declared that they need to change the state motto from "Live free or Die" to "Live, freeze and Die". Newport R.I. isn't on the list?

  9. Shouldn't New Haven be on the list? You know, Yale and all.

  10. I had to laugh when I saw “arguably none” for VT. I have to agree. There are small tastes of preppy in parts of the towns in the list, but I never encountered anything very preppy in day to day life in the Burlington/Shelburne/Charlotte area in which I spent most of my time. Lovely state, though, and I do miss it.

    1. I figured Orvis originating in Manchester, as well as the history and revived presence of the Equinox there; the appearance of Putney and Stowe; and Bennington (artsy edge of preppy) deserved consideration.

    2. When I drive through the center of Woodstock, VT on my way to visit the rels in Western VT, I like to play "spot the locals." It's easy -- they are walking briskly and purposefully (unlike the hordes of idling, gawping tourists attracted to this charming place) and are wearing unobtrusive, sensible, time-worn prep clothing. The traditional hairstyles of the women, the belts on the men's rumpled khakis, and the unaffected bearing of all of them - including their dogs - would be recognized right away by SWNE readers. Even though there's no "SW" there.

    3. "As you walk down Main Street of a Saturday morning, you can see two schools of dress. The first is loud with striped overalls, plaid woolen shirts, boots and sunbonnets. These are the city slickers. The second is modest and conservative, with hats, ties, silk dresses and polished shoes. These are the country people. There is no animosity. Each respects the others' habits, except when city people begin ambling around the village dressed in little more than a couple of handkerchiefs."
      "Your House in the Country," Mins, 1940.

  11. Thanks for the list. Would like to retire someday. I am torn between Connecticut and Virginia. Connecticut is so pretty and has close access to NYC and all the cultural attractions. Virginia has milder weather and close access to DC. Are there any preppy towns in the South?

    1. While I live Connecticut I vote for Virginia!! I live in Texas and plan to go back to Virginia in the next few years. In Virginia you'd love Charlottesville, which is very preppy. Middleburg, Aldi, Upperville for horse country WASP. You asked for preppy towns in the South - Charleston, SC. Charlotte, NC. Almost every Southern state has a city or suburb that is preppy/WASPy

    2. I agree. I love Connecticut but Virginia weather is better and Charlottesville and the nearby mountains are charming. I think there are definitely a few areas in the South that might be considered "preppy."

    3. I think Alexandria is preppy in a Southern way. Leesburg has lost its charm. If you're torn between Virginia and Connecticut, there's nothing wrong with having a place in both places. But if you want the real South, I'd say South Carolina or Georgia. Probably not Florida, though.

    4. I should have included Irvington, Virginia, and the surrounding area, a quiet and reserved town on the Northern Neck. No nightlife to speak of and lately popular for weekend places on the water for people from Richmond. Good for boating and sailing but waterfront property is a must. Investment firms maintain local offices, good Episcopal boy's boarding school nearby, historic churches, country club. Closest Volvo dealers are in Richmond and Fredericksburg, same for Mercedes Benz. Land of pleasant living.

    5. I live in Lexington, VA, which used to be preppier than it is now. Washington & Lee University and Virginia Military Institute are situated beside each other. It is safe, peaceful, and has some charm. There are only two decent restaurants at this time. A J.McLaughlin store opened back in November, but that's the only chain store in town. There are many stellar alums, including the late Tom Wolfe who always visited at least once a year for the annual "Tom Wolfe Seminar." It is one hour from Charlottesville, which is much more commercial. It's an hour from Roanoke in a different direction. Because of the schools, there are opportunities for hearing interesting speakers and attending various performances. It is quiet living that is easy, and many alums of the schools retire here. The grocery stores are lacking, but no one seems to be going hungry. You can travel to Charlottesville for Whole Foods and Trader Joe's. Medical care could be better, but for something very serious, there's UVA.


    6. Thanks for the great suggestions! Will research them carefully. :)

    7. If you go to Roanoke instead of Charlottesville, you don't have to cross the mountain.

    8. Please do not move to coastal South Carolina. All of the horrendous growth is destroying our wetlands and woodlands. Every time I turn around there are new neighborhoods, new roads, and way too much traffic. It's heartbreaking.

  12. Here I was just looking forward to crocus and now I'm longing for beach roses.

  13. None of the Massachusetts towns on McSweeney's list made your list:

    Blight Falls
    West Lameham
    Unstable (/unst’-a-bull/)

    1. HAAAHAHA!!! I need to know - what is McSweeney's list?? Does it include North Bendover?

    2. Hours of entertainment await you at

  14. I feel like the word "preppy" and prep values in general are being lost- punctuated by many of the towns on this list. I see a lot of "New Yorky" towns... money and range rovers... which I'd argue is much less preppy than just purely wealthy. I think "preppy" connotes a certain restraint and Yankee practicality (i.e. Dover vs. Wellesley) which is endangered in many of these places- Osterville, Nantucket, and much of Fairfield County for starters.

    1. Anon 11:04, you are absolutely right. Way too much new money and status display in several of these places. I wonder how many of their nouveau-wealthy residents would even consider a significant donation to their local historical societies? Probably not PR-worthy enough.

    2. Sadly agree about Wianno/Osterville/Oyster Harbors. I grew up summers there in the fifties and sixties. Good humor trucks in the dusk, caddies from local clubs hitchhiking to and from town picked up by everyone, rolling inner tubes down the road under the old streetlights, the local police stopping to give us rides when walking back from a friends house in the dark. Long time past.

  15. I would respectfully add Gloucester, Provincetown, Sudbury and Wellfleet, Massachusetts; Bennington, Vermont; York Harbor (but not York Beach) and Cape Neddick, Maine; Middletown and Newport, Rhode Island; and I would subtract Brattleboro, Vermont.

  16. As others have mentioned Charlottesville and some of it’s surrounding smaller towns (Crozet, Batesville) are very preppy. Fox chasing, polo, and steeplechase are still very active. The amount of local restaurants and vineyards can be overwhelming. The only drawback is that the population is much too high due to the University. Additionally one easily can hop on a train into DC and pop over to Georgetown which is still very “preppy”. But again, the students..
    JM, Virginia

  17. It may be a bit off-topic but I just keep scrolling through the nice pictures thinking about Spring. Now I’m sitting here in small town South with a pair of Sperrys so old that the toes are sorta pointed and my BB ocbd with the rolled up sleeves is getting a bit worn and we gave our last Fijord to a granddaughter and now we are driving a real Ford with a dealer 3 miles away so I really can’t add to the discussion but I would suggest you take another look at the pictures and think - Spring ...and that happens in all the locations mentioned.

  18. As a pretty traditional New Englander, I really like (and feel comfortable in) Charlottesville, VA and Charleston, SC. But this blog is specifically "Salt Water New England," so maybe someone else could start a Southern Prep blog, if there isn't one already?

    1. A couple of Florida towns would include Ponte Vedra and Vero Beach! Also, Palm Beach, Sarasota, and Naples!

  19. I thought I saw Southwest Harbor, Maine on the list when first published, was it removed or was I dreaming?

    1. Yes, I would add Southwest Harbor and also Winter Harbor (Grindstone Neck area principally--"Philadelphia on the rocks").

  20. An interesting kind of evolution usually takes place in towns like this. Maybe not all, but in the ones I've seen, they start out as low key quaint places, with no show, and a relaxed life style. Houses are modest, weathered grey shingles. Modest car comes over on the ferry. People in supermarkets are courteous, and famous people are not bothered. Then a change takes place gradually and then at a fever pitch. The masters of the universe begin arriving. Palatial homes; narrow streets jammed with Range Rovers. Dress goes from relaxed , showing wear, to those wanting to make a fashion statement. Still just one supermarket on the island, but it is jammed. An example of the coarseness that has arrived took place when one of the masters of the universe showed up at the 6 items or less line with a huge cart of groceries. The clerk advised him that this line was for 6 items or less. "Not now, he said", as he took the sign down.

  21. Glad to see you resurrect this post, and particularly the photos, as we get through the doldrums of the winter months. Can't wait to get outside and enjoy all of the experiences that come with the beauty of this area.

  22. My additions would include Dorset, VT and Blue Hill, ME

    1. And while you are at it add Bucks Harbor (South Brooksville), Maine.
      Home of the very prep Bucks Harbor Yacht Club and where the children's classic "One Morning in Maine" took place.

    2. I loved reading "One Morning in Maine" to my children (second only to " Time of Wonder").


  23. Replies
    1. I completely agree. My great-great aunt, who was English, had a home with a garden that the queen would have approved of. As kids we would go to the Cape in the summer and visit her in Cotuit for afternoon tea, bocce and croquet. (her husband was the owner of Sportcraft).
      Bulgaria SWNE fan

  24. Might add that's it's very preppy to a make of what constitutes preppy... just an observation, not a criticism, having memorized nearly every list (and written word) published in the "Preppy Handbook" myself, decades ago... Anyway, how is Block Island or Newport not on the Rhode Island list?

  25. Ha! My town is missing from the list. Thank you.


  26. Amherst should almost unquestionably be on the Massachusetts list, with the exclusive Amherst College, Hampshire College, Smith College, and the University of Massachusetts Amherst; renowned poets Emily Dickinson and Robert Frost also resided in Amherst for their writing careers. It's town seal, the book and plow, represents the town's devotion to academia, and with elite schools such as Deerfield Academy, Eaglebrook School, and the Williston Northampton School right next door, Amherst could hardly not be considered a preppy town.

  27. Old Greenwich, Conn. But not Greenwich, Conn.? What would GHWB say?

  28. South Freeport, Maine (distinct from Freeport, Maine)...just above Yarmouth but decidedly more relaxed in an old-school preppy way