Photo by Salt Water New England

Saturday, April 20, 2019

A List of Preppy New England Towns

All Photos by Salt Water New England
What are the classic/preppy New England towns?


Over the decades, the adjective "Preppy" has been changing, from describing the summer person who picks up litter to, now too often, the tourist who drops it.  Be that as it may, 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? 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
?? - Really on the fence
. - Strong examples

Pictures from Salt Water New England


  1. Under Massachusetts: Lincoln, Groton (how was this missed?!).

  2. Thank you for taking so much time to take all these pretty photos and for sharing them.

  3. I agree. How about Littleton Common, near Groton and Lincoln? I would assume such a British sounding location must be very preppy, but I have never been there so who knows!

  4. Suffield Village, CT. Impressive walkable historical district including numerous preserved 18th and early 19th Century houses and churches, Suffield Academy boarding school, much open space, Connecticut River canal frontage with a bike path, good library, surrounded by former tobacco farms, no big box stores, restaurants all owned by locals, low key country club with golf, tennis and paddle

  5. Prouts Neck, which is in my town of Scarborough, is not entirely private. The Prouts Neck Cliff Walk is open to the public, but the parking is not, so some people bike or walk over. Guests of the historic Black Point Inn and dining have access. Prouts Neck Country Club owns a large part of what people call Ferry Beach, but only a relatively small portion of that belongs to the town. When one goes around the corner that’s parallel to the club, it’s no longer town property. Even so, Prouts Neck has kept it open to those who visit Ferry beach (which charges during the summer season). I didn’t learn that until last year when I trained to become a plover monitor on the beach. There is a summer Episcopal chapel at Prouts Neck which is behind the gate so it does not welcome all; it’s for residents families and guests only (so I was told). They also have their own private historic library and the Winslow Homer studio which one can access via a special ticket from the Portland Museum of Art. If you visit Prouts Neck don’t go above 25 mph on Black Point Road because you will get pulled over. And I mean don’t even try 25.8 mph. I recommend dining at the Black Point Inn on a beautiful summer day or evening where you can sit outdoors. We're regulars, but it's only open seasonally.

    Scarborough is an incredibly diverse place. We have beautiful sandy beaches (Higgins, Ferry, Scarborough State Park, Pine Point), a large organic farm (Frith Farm), seasonal farmer’s market and farm stands and a large senior population with excellent support services (and home to Piper Shores, a beautiful retirement community by the sea). We have a multitude of nature preserves and hiking trails. We have our own indie health food store and cafe that’s been open since the 1990s. Our public schools are highly rated. We have an Audubon Center on the marsh. There’s a large surfing community here, too. We do not have a quaint historic downtown, though. While Scarborough is a mostly affluent town there is definitely poverty, too and not all of it is “genteel”. Over the past ten years there has been rapid “development” of new cookie cutter type housing, condos and apartments on what was once wooded and open spaces. We’re also a bedroom community for Portland.

    In summary, I suppose one could say Scarborough has pockets of preppy along with the enclave. Rapid development aside, I love living here!

    I would add Kennebunk and Yarmouth to the list.

  6. In Massachusetts: Definitely "Swellesley"

  7. Arcadia ... what the Founding Fathers dreamed America could be. A shame so much of the nation doesn't look like this anymore.

  8. In our neck of the woods, Marblehead and Newburyport in Ma., definitely. Rockport, Ma. has taken on the aura of a tourist trap, in my opinion though. Glad you did not include Salem, Ma., which is not only the most "UnPreppy" place possible, but also the most unhealthy place. If it's true that only about 17% of people smoke anymore, then it's the case that 95% of them live in our town of Salem. And nearly all the visitors enticed here by the witch vibe, rather than the literary, maritime, and architectural history of the town are smoking and vaping on every street and corner of the town. Hate to be critical, but the filth and grime of the town and most visitors gets to me sometimes. Chestnut St. is still an oasis, though. Looking forward to visiting some of the other spots. Still a believer in Cape towns of Chatham and Orleans, too. Thanks for all the wonderful photography. You do for the New England area what David Patrick Columbia does for New York City in his New York Social Diary. Keep up the great work.

  9. Rhode Island:
    Barrington without a doubt, Bristol = Yes, Little Compton for sure, adding Tiverton, adding Warren, and yes to the rest. Feeling like Newport is losing its way a bit.

  10. Poor old lower Fairfield county! So many question marks! The dowager is damaged, but not fallen.

    New York is not New England.

  11. listened to this music as I look at your excellent so well!

  12. Thank you so very much for all your pictures here, such food for the soul....

  13. In New Hampshire, I’d definitely add Hancock and Wolfeboro. I’d also consider adding Center Harbor, Center Sandwich, Exeter, Meredith, New London, and Peterborough. Fantastic list, though!

  14. Such wonderful photos. Thank you very much.

  15. If NY can hypothetically be included on this SWNE list, where do we fall on the rest of the mid-Atlantic? Is it more about culture or just geography? I would argue from my time there that towns like Princeton, NJ fit the criteria better than Fairfield County or some others on this list.

    1. Request was preppy New England. New York and New Jersey are not part of New England. New England consists of Maine, New Hampshire, Vermont, Massachusetts, Rhode Island, and Connecticut. It's about geography in this case. If you want to talk culture, there are thousands of places outside Fairfield County/New England that are more charming/preppy.

  16. As a New Yorker who married a Mainer and spends a fair amount of time in Maine I can say we, NY, are not New England nor do we want to be. However, being very familiar with Clayton NY, I agree that it could go on this list. Sackets Harbor is another distinct possibility. NY has its own vibe; the diversity of the landscape has created micro societies. The Adirondacks, St. Lawrence river valley, Hudson river valley, Finger Lakes, southern tier and of course the city, have little in common in terms of culture. We even have colloquial distinctions that a lifelong state resident might be hard pressed to identify. I love, love New England and all of my ancestors, patriots that they were, hail from there but I do love me some NY too!

  17. Why not Neport RI?

  18. No love for Exeter, NH, Port Clyde, ME or Annisquam (although I suppose it's considered part of Gloucester)? Ipswich, Essex? Feel free to nix the ?? towns, and I'd add a ? to Winchester which has gotten awfully precious. Or maybe I'm conflating Preppy and Yankee; there is a distinction.

  19. Simsbury, CT should be on the list for CT. Big crew team and actually has a prep school (Westminster) in town. Origin of the word preppy used to include time spent at a prep school. No?

  20. Wianno/Osterville on Cape Cod?

  21. Having recently been to Bronxville, New Canaan, and Darien, I can safely say that they are indeed preppy (enough).

    1. I was definitely surprised to see a ? next to my home town of B-ville. We New Yorkers do not identify as New Englanders, though.

    2. My comment on New York was not a dig just to clarify. It is basic 5th grade history. Patsy, can you honestly tell me Bronxville has not changed? My cousins live there, and even they who are pretty chill about these things say it has. Your comment is a perfect example of why Fairfield County has so many question marks. New Yorkers do not identify as New Englanders... Particularly Manhattanites, or from the surrounding boroughs.

      Do not equate New York and poor behavior in my next comment, or indeed any of my comments. Anon 7:10PM, I believe if you were a long term resident of New Canaan and Darien you would have experienced a dramatic change. Both towns were two of the most prolific tear down towns (and the most profitable for builders and remodelers) in the last boom. Residents thirty years ago would have been mortified to be seen in town behaving the way some current residents sort of feel proud and entitled to behave. I don't think this is particularly unique to Fairfield County to feel the flavor and charm has changed. I've experienced the same changes in the San Francisco Bay Area with the city and the surrounding commuter towns changing a great deal. Cities/towns that were very "preppy" in the way described above have all changed in the same way.

    3. Not sure what your question is? Has it changed? Of course it has. My grandmother's millinery shop is gone. The lunch counters in the local pharmacies (where my dad short order cooked in high school) are gone. The shops where my sisters I sold cheese and shoes and scooped ice cream (not all the same place!) are gone. And, judging from my friends and family, seems pretty preppy. Still not in New England, though - lol.

    4. Lol!

      Those are the niceties I am talking about!

  22. Dover, New Hampshire, is not "preppy" however that is defined when applied to a town. Dover was a mill town, and is now something of a college town/overflow for people priced out of Portsmouth. This is not a dig at Dover, which has much to recommend it, but it is not in the same category as Newburyport or Marblehead. As other posters have noted, Exeter (if only because host to the school) or Wolfeboro may better fit the bill.

  23. I've noticed Groton, MA has been mentioned, but for Massachusetts I'd also like to humbly submit Carlisle (they have a wonderful general store called Fern's in the village center), Ashby and Northfield.

    Ashby is the least populous town in Middlesex County. It's filled to the brim with old farms and a quiet but quaint village center that is still mostly independent local shops more common to farm towns in New Hampshire and Vermont).

    Similar to Ashby, Northfield is a small rural farm community with local independent shops (the town gathering place for all types is Mim's Market General Store). It sits on the Connecticut River at the Northern end of the Pioneer Valley - a stone's throw from New Hampshire and Vermont. The town center sits less than a mile from Northfield Mount Hermon boarding school, and I can attest to the amount of classic European cars that come out of the local barns starting around mid-April. Northfield, while not as high end as some of the other Massachusetts towns mentioned, seems to be the eastern-most of those close-knit and hearty New England towns that can be found in the Pioneer Valley and the Berkshires.