Photo by Muffy Aldrich
The Modern Guide to The Thing Before Preppy

Tuesday, July 5, 2022

New England Preppy Towns

Photos by Salt Water New England

From a reader:
Hi Muffy,

Can you please re-post your list of classic New England towns from a few years ago, as well as the selection criteria used?

Thank you!

New England Preppy Towns

In the past, this community has generated this list.  How would you change it?

  • 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
  • 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 
  • 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
  • Watch Hill
  • Wickford 
Vermont (Some may say none, but others would include...)
  • Brattleboro
  • Burlington
  • Charlotte
  • Grafton
  • Manchester 
  • Middlebury
  • Newfane
  • Norwich
  • Putney
  • Shelburne
  • Stowe
  • Waitsfield
  • Woodstock 


What are the attributes that make for a preppy town?

My list of criteria, in no particular order, include:
  • Architecture and historic preservation; 
  • 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; (and the absence of Black Dog stores);
  • Quality of harbors and/or miles of coastline;
  • The number of dogs being walked; 
  • Egalitarian spirit;
  • Services for seniors;
  • Percentage of people wearing some variation of The Uniform;
  • Availability of parking spaces downtown;
  • A productive hum, neither inert on one hand nor overheated and competitive on the other.
What other attributes would you include?




  1. Labradors, Golden Retrievers and perhaps an occasional spaniel or terrier. NO DOODLES

    1. Let me second NO DOODLES. Never has a comment spoken so clearly to my heart.

  2. On occasion, I see a MINI Copper in the photos. Is it safe to say the MINI is a preppy car spotted in various New England preppy towns? Or is that a huge leap?

  3. Such wonderful photos! You always capture the mood, feeling, and the respect perfectly! Thank you so very much, for all you do for us! Cheers!🇬🇧

  4. That word "preppy" ought to be eliminated from the English language. These are traditional, classic New England towns, and "preppy" is not a traditional English word--it describes nouveau riche upstarts.

    1. Bravo! Well said!

    2. @ Anonymous: Tell that to Jennifer Cavalerri, aka Mrs. Oliver Barrett IV. After all, it was she who referred to Oliver as "preppy" when first they met in the Radcliffe library.

    3. Paul, she wasn't praising him.

    4. Uhhh, duhhhhhhhhh. However, most folks consider that line in the movie to be the cultural first reference to the term (at least in contemporary times).

  5. Vermont’s list needs add Danby, Dorset, and Langrove. Brattleboro and Burlington can be subtracted. Manchester holds on thanks to The Equinox. There are, otherwise, way too many shopping day trippers.

    1. I submit Greensboro - in the warmer months - for consideration.

    2. Yes to Dorset, Landgrove and also Weston as well as Arlington in VT. Danby not so much- a bit of the hinterlands from Dorset. Manchester (Village more than Center) is as clubby as it gets in VT. And absolutely not on Brattleboro. The farthest thing from traditional one can find in the state.

  6. It would be great if the places where the photos were taken were identified.

  7. Unfortunately, Portsmouth, NH no longer meets the criteria. There are more restaurant seats than citizens and I can’t think of a single farm.

    1. Surrounding towns have plenty of green space for a coastal town (Newington, Stratham). Might consider adding Newcastle, NH; Avon, Simsbury, and perhaps West Hartford CT (Farmington but not those towns?); and Gloucester and Sturbridge, MA. Also, unless tourists are a disqualifier, Newport, RI.

  8. A needlepoint shop

    1. Certainly at one time. Sadly had to find anywhere now.

  9. Edgartown is certainly quite preppy by many criteria (Anonymous at 12:08 a.m. notwithstanding), but note that it does have a Black Dog store. :)

  10. West Hartford, Avon and Simsbury should be on the Connecticut list.

    1. Farmington I see on the list. Avon and Simsburr are “want-to-be’s”
      West Hartford is, to its credit, way too diverse to be labeled “preppy.”

    2. That sounds about right, about West Hartford. It is is diverse. One might expect Greenwich itself, also, to be on this list, not just Old Greenwich. Like someone noted, towns can vary by neighborhood or section. Greenwich is actually quite diverse. Big business and big bucks bring in all kinds of people, from Asia and Europe, as well as the USA. Few of them pop their collars.

  11. Shelburne and Charlotte are absolute gems. It doesn’t get much more ‘preppy’ than all of Electra Havemeyer’s collections on display at the Shelburne Museum.

  12. West Hartford is really cute. Great resturants!

  13. Um, relatively trim people -- not letting oneself go, moderate food intake, some physical activity even if it is limited to routine walking, etc. -- in most public spaces that one might encounter others?

    Kind Regards,


    1. Must we body shame? Just because someone doesn’t align with your ideal physical archetype, that’s not a reflection on their moral worth. Assume what you will, but what do you really know about another person’s struggles? We’re not here to support your aesthetic requirements.


    2. Mike, you are right. On further reflection, I put my foot in it and should not have made that thoughtless comment. As parents and grandparents used to council the young H-U, "If you have nothing nice to say. . ." Mia culpa and peace.

      Kind Regards,


    3. Thanks, H-U. I may have been a bit more strident than warranted; I have people close to me who have struggled with the issue, even though they have worked hard to achieve an ideal that is probably unattainable. Many thanks for your follow up comments. All the best.


    4. This sort of honest, equitable, civilized interchange marks the readers/commenters of this blog as really decent human beings -- as we know, increasingly uncommon on the internet. You two have revealed yourselves as true gentlemen.

  14. You forgot to mention Episcopal Churches. After all, for all intents and purposes and until the mid-1960s when it veered hard Left, the Episcopal Church was the "establishment church." 25 Presidents of the USA were Episcopalians. There used to be a saying that "the Episcopal Church was the Republican Party at prayer." However, that is definitely no longer the case.
    I would venture a guess (and without referring to the Episcopal Church's website Church finder, that every town you mentioned in CT and the other New England states has a local Episcopal parish (or did in the past).

  15. I know the blog is New England based and oriented, but would love to see a version of this for the Mid Atlantic — down to around the DC and VA regions. Tragically, where I grew up in NJ has gone from staunchly preppy to alarmingly nouveau riche in recent years. I am desperately in search of any remaining bastions of tasteful tradition in this neck of the woods!

  16. I live in a part of Northeast Ohio that was formerly the Connecticut Western Reserve, and as such we have a lot of little old towns with a very New England flavor to them! Chagrin Falls and Hudson definitely come to mind!

    1. Add to the list Ravenna

    2. Bay Village, OH certainly falls into the above category. Coastal and refined without any pomposity.

    3. Gates Mills and Shaker Heights ( not so much anymore, we were intergrated back in the day and very preppy with a sort of midwestern, nerdy hayseed flavor). Great public libraries are also a must.

  17. Private clubs, private schools, but still egalitarian? Does the genteel poverty account for all the old cars in the photos?

    1. Ha! Good question. You’ll end up poor keeping one of those old MG’s on the road.

    2. My question was probably in poor taste. In any event, I think Amherst belongs on the list, although it's not on the coast.

    3. I don't think your question is in poor taste at all. But I don't think the two are irreconcilable. Most of the places on this list are indelibly marked by privilege. But in the best places (some small subset), there exists an inherent respect for those of all classes and yes, in some cases, an "egalitarian spirit." Let me give an example. One of our best friends in Maine has more money than any of us will ever see. The last time we had dinner over there I was seated between the commodore of the yacht club and one of the local characters who is caretaker and odd-jobsman for many of the houses. The pastor who serves the little church for the summer was across the table, seated next to Mr. Exeter/Dartmouth the III or IV. This is typical – and fun. Last summer a young couple from out of town opened up a bar in the town and my friend had their children over to her house a couple of times a week to play with her grandchildren and make friends. My friend has a woman who comes to clean once a week and paid for the woman to have dental surgery so she could fix her teeth; this surgery literally changed the woman’s life. She also bought the local ice cream shop one of those battleship-sized cappuccino machines to help them make a better go of it. Now, I know that in the scheme of things all this is a drop in the bucket, but I think it does speak to a sense that the entire community relies on one another, regardless of class or education, to make things go, and that one is not valued more than another. I think this story may be more true of summer places, although of course it can also operate in reverse.

    4. Those are very nice comments about community. I grew up in a small town at a time when small towns were very city-like and at one time were even described as urban (Around 8,000 when I was born). It's nothing like it was when I lived there. The major employer, a railroad, relocated, and the downtown business district is a shell. That's true of many places larger and smaller, for reasons you might guess. The big box stores took over and are even located outside the city limits, to make things worse. The result, from a community standpoint, is a lack of local business leadership that actually lives there and is concerned with the town as a community. Anyway, that's my theory.

  18. Sorry Vermont but you just don't cut it.

    1. On what grounds?

    2. A real Vermonter would not be caught dead with a sweater draped around their shoulders.

    3. I'd venture to say that everyone I went to prep school with wished they were Vermonters. Nearly 100% of them spent winter weekends skiing in Vermont and many of them live there now.

      While Vermont is obviously not a coastal state, there is a certain element of "prep" found there that I think is missing in many other places on this list. For example, Vermonters take excellent care of their natural spaces and have a great appreciation for high-quality locally made goods. Also, you'd be hard pressed to find a farm that isn't a trophy wife's pet project in many of the places on this list, while Vermont is almost exclusively farmland.

    4. For "prep" Vermonters, it's less the clothing and trappings and much more the ethos.

    5. Vermont is more Portland Oregon, than Portland Maine. Any "preppies" are from introduced or migrating stock, the native breeding population was extirpated in the 1970's. The poor sailing conditions on Lake Champlain should also be enough to disqualify VT. Please leave your angry replies below.

    6. I think the intended comparison belies the lack of familiarity of the two places. Is Portland Maine really 'preppy' and by what, dint of islands and seafood? Seems more like a lot of bachelorette parties and, as with nearly anywhere in Maine, hard to find anyone 'preppy' who is from there vs. from away. Meanwhile Portland, OR has some well-to-do, clubby and perhaps even 'preppy' hoods in/around it. Lots of other spots on the above list also would struggle to produce good sailing conditions, if that's truly the single most important variable in defining what is 'preppy' vs. what is not, though that seems a bit more like a layman's definition vs. an informed one of what makes for a 'preppy' town (the above bullets do a more fulsome job of defining the types of towns, imho).

  19. what about East Aurora, NY?

  20. Millard Fillmore would agree.

  21. I grew up in Bridgewater, CT, went to public high school in Washington, CT, and now live in coastal Rhode Island. Sadly, the fabric of the towns on the list that I am familiar with has changed immensely with the obscene amounts of money people are paying for houses. They have leveled houses that have been in the towns for 100 plus years in order to build their McMansions, planted evergreens around the property perimeter to obscure the views everyone used to be able to appreciate, and make no attempt to become a part of the community. It’s very sad.

  22. Though technically New York I would add Fishers Island

  23. In the same way that Black Dog stores are disqualifying, so are Sea Bags stores.

    1. Interesting - small, made in America businesses are disqualifying. Thought this was part and parcel of New England values?

  24. How about downtown Greenwich Ct ? I love this list. Its one of my favorite posts.

  25. I believe in the past Muffy noted especially bright examples on the list (with an asterisk perhaps). Muffy, could you please do so again?

  26. I think a prerequisite to any place, person, or thing being thought of as preppy is people who think in such terms and concepts. In my experience, those who think that way were often largely formed before Sgt. Pepper was released. Younger persons thinking about the state of preppiness of place, person, or thing, are in my experience, likely to be thinking of preppy in a more gauche and possibly derogatory way with more than a smattering of elitism.

  27. All of these towns have several things in common: great wealth inequality, little ethnic diversity, and next to no factories where anything is manufactured, so there are few middle-class incomes outside of the colleges and some government jobs. They are also home to elected officials who claim to be opposed to all of the above. Some might argue the real factories are the aforementioned colleges, which are turning out miseducated conformists in record numbers.

  28. Well, Andover, MA has Raytheon, Bausch & Lomb, Pfizer, and MKS Instruments, for starters. Phillips Academy is intensely diverse - students as well as faculty. Right on the border of Andover and North Andover (a very middle-class town, but which also has a prep district in the Old Center and around Lake Cochichewick) is Merrimack College - NOT an Ivy - with a progressive curriculum which would negate your final statement.

    1. When I refer to manufacturing, I am talking about consumer goods. Actually, Raytheon is a good illustration of what is left in New England. They are almost exclusively a defense contractor and therefore must produce domestically. Most of their work is funded by the taxpayer. Their missiles and other weapons systems are not useful to the general public. I also excluded the other semiconductor companies around Route 128 for many of the same reasons. A better example is the shoe industry. The only shoe factories left in New England are Alden and a few higher end models made by New Balance. Small volume of shoes produced exclusively for rich men. Of course, the prep schools themselves are diverse. They have recruitment and hiring targets they must fill. In this case, I am referring to the “townies”. It is understandable if they are excluded in your analysis, since they are mostly invisible to the preps and those who run the schools, except if they are in service roles. I can understand a few of your points, but you finally lost me with the benefits of “progressive curriculum”, which seeks to "cancel" everything and anyone in opposition to it. I saw this first-hand at one of these preppy towns in Vermont, with a mob seeking to shut down a visiting speaker whose views were unpopular. Unfortunately, the damage progressives are wreaking is not limited to impressionable college students. We are seeing the practical results of this philosophy every day at the grocery store and gas station. Punishing the very people that progressives proclaim to champion, the least privileged among us.

    2. You’re right. Submarines, heavy lift helicopters, and jet engines, “are not useful to the general public.” When I was a boy, growing up in Connecticut, my father drove the family this way and that way 70 miles to visit our grandparents. As we passed though each small town, good size town, or city, my dad would say “this is where they make...” Among the many, hand tools, shirts, sneakers, even nail clippers. Now all that manufacturing is gone. It didn’t even take a lifetime.

    3. Oh, I think it may have been more than a lifetime, but I take your point. Manufacturing used to be quite widespread throughout the country, although it still is more than you might think. The growth just isn't where it used to be. I mentioned that the main industry in my hometown was the railroad. In addition to locomotive maintenance, which steam required a lot of, they manufactured rolling stock. About a thousand men worked there. But there was also a Maidenform plant, too, also gone. Don't know how many worked there but I expect mostly women. Incredibly, the second-largest employer in town was a laundry-dry cleaning operation, founded before World War One. That was before wash & wear, when people dressed up a little more. Nothing preppy about the town but it had its nice neighborhoods. That's where the best Christmas decorations were.

      Not all manufacturing went overseas. Some merely relocated to other parts of the country. That is still happening and for the same reason. All is not lost, however. There are numerous car factories owned by foreign car manufacturers in this country, mostly in the southeast. Hard to believe, really.

      Is there still a New England fishing industry?

    4. The dwindling American manufacturer, especially of consumer goods, is present across the country. One might even argue that New England has retained more than most (Alden, Mercer, Rancourt, Quoddy, Eliza B/ Leather Man. Aside from the fact that I love their wares, it makes me feel good when anything I buy, be it a dust pan and foxtail, a lawn mower, or a pair of pants, bears that Made in the USA label. By the way, I notice more and more foreign made (and I am not referring to UK woolens) goods creeping into stores like Press that I once thought of as bastions of American-made clothing.

    5. I agree with you wholeheartedly, both with your facts and sentiment. Please note, though, that with the exception of Eliza B (which is not really a factory), I don’t believe any of the places where these fine New England products are manufactured made the cut on the “preppy town” list. Just coincidence?

    6. The cod and haddock fisheries have virtually collapsed. Though there may be some tentative signs of reversal. Scallops are holding steady. Not sure about lobsters. There is a lot of oyster farming. Nice sweet, fat, briny oysters are grown all along the New England coast. If anyone offers you an oyster from the Damariscotta River in Maine, don’t dress it. Eat it naked.

  29. Please. Ignore not the Berkshires. Add South Egremont, Southfield, and even Lenox. Thank you.

  30. I had the quaint idea that 'preppy' meant having gone to a prep school. So, a New England town with a quorum of prep school graduates located on the coast (with a good harbor) should qualify, whether or not it has it has a good Triumph mechanic or organic farms, presumably outside the township line, where the gas stations, McDonalds, and Wal-Marts are, just off the interstate. In any event, parking downtown isn't going to be easy.

  31. Where is Greens Farms, Connecticut I wonder? Do you mean Westport - Greens Farms?

    1. Greens Farms is certainly the preppier part of Westport as compared to say Saugatuck.

  32. No East Hampton, Connecticut? Just kidding. We, as west coasters, landed in East Hampton and it was to me as beautiful as anywhere in New England, though not very preppy. We lived just up the street from Lake Pocotopaug and enjoyed quite a beautiful view from our dining room. Our second son was born in Manchester and thinking he'd be our only east coast baby we named him Easton. A third son was born right in our 1800's home in East Hampton. I left my heart in New England!

  33. I would submit Sudbury, MA as a contender. Also I am not aware of Fairfield - Mill River as a neighborhood.

  34. Ridgefield, CT is a must add. It is a colonial town with historic sites for the battle of Ridgefield. It also boasts the Keeler Tavern Museum and many historic homes lining its beautiful Main Street. Add to that numerous horse farms (the real kind) and bucolic countryside. Not on the water but its residents find the shore easily through the various clubs in neighboring towns. There are also a number of lakes for swimming.

  35. Almost all New England towns, preppy or not, have a Congregational church (often of the classic, white-steepled variety). But only the preppier towns also have a prominent Episcopal church (often of the stone, square-tower, pseudo-quaint-English-village variety, and often located right on the town green). Among many others, see Christ Church, Guilford; Grace Church, Amherst; St. Andrew's, Longmeadow; St. Stephen's, Middlebury; St. Andrew's by the Sea, Hyannisport; St. Ann’s, Kennebunkport.


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