John Giuffo

John Giuffo, Contributor

4/12/2011 @ 01:30PM |59,311 views

America's Prettiest Towns

Cooperstown, N.Y.

Mention Long Island to most people and shoreline McMansions and celebrity-studded soirees in the Hamptons may come to mind, or acres of suburban tract housing dotted by strip malls.

But hidden away at the tip of the North Fork, far from the famous and the fatuous, is a town that perfectly mixes unpretentious Americana with the trappings of the modern food and wine scene. Landing a spot on our list of prettiest places, Greenport is perhaps Long Island’s most attractive locale–quaint summer cottages push up against old-school seafood shacks and fancy restaurants (the inventive seafood options at The Frisky Oyster never disappoint), with beach and boating options never more than ten minutes away.

In Pictures: America’s Prettiest Towns

“Things are much more low-key along the Peconic Bay on the North Fork,” says Jason Clampet, online editor at Frommer’ “Although Manhattanites have brought art galleries and coffeeshops with them, Greenport’s small inns, pebbly beaches, and fishing heritage still cater to visitors who’d rather relax than star-gaze.”

Working with travel experts from Frommer’s, Rough Guides and Midwestern Living magazine, we’ve pulled together a list of some of America’s prettiest, most enchanting towns. We looked for places that offer not only aesthetic bounty, but memorable activities and destinations nearby.

Day-trippers from New York City who aren’t in the mood for a sun-and-surf-drenched weekend might prefer Cooperstown in upstate New York. “There’s lots of period architecture, there’s a little bustle trolley that runs around the town, and you’ve got the whole natural vista of the Catskills,” says Nick Edwards, an author for Rough Guides who has written about nearly every U.S. state. “It’s not touristic in any sort of tacky way.”

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  • beachbuilder 4 months ago

    All of those places were beautiful BUT people often overlook Lake Michigan. Charlevoix is pretty but it has nothing on St. Joseph, New Buffalo or South Haven Michigan. I wish someone would do a piece on Chicago’s Hamptons….Southwest Michigan.

  • greggferndale 4 months ago

    Thanks for featuring Ferndale. It’s a great little town surrounded by the redwood coast. Want to see more? Go to

  • cedarreuben 4 months ago

    The author is spot on about Ferndale, it’s a beautiful town with a unique “lost in time” type of character. In fact it’s been used in a number of movies as a location set. Some other beautiful locations in Humboldt County are the towns of Arcata and Trinidad.

    Arcata is a hip college town filled with authentic Victorian architecture while Trinidad is tiny town next to the sea. Both are great places to visit or stay while in Humboldt County with great food, easy access to the Redwood forests and beautiful beaches.

    As an added bonus Arcata has dozens of innovative businesses producing unique products. Just a few examples are Fire and Light which produces dinnerware from recycled glass, Hilliard which makes custom cast bronze lighting fixtures and Marimba One which makes world class marimbas. Check it out!

  • John Giuffo John Giuffo, Contributor 4 months ago

    Thanks for the kind words. We did a feature where we mentioned Arcata a couple of months ago, but it definitely stood out as another California town that warranted a mention.

  • John Giuffo John Giuffo, Contributor 4 months ago

    Thanks for the recommendations. I will keep those towns in mind for future travel stories.

  • jodamiller 4 months ago

    Nice to see my tiny hometown of Hermann, MO included in this list.

  • lidarkside 4 months ago

    Having lived down the road from Greenport, NY, I would hardly put it on the list of prettiest towns in America.

    Granted, they have been doing a good job at fixing up the main street, they have the carousel, and they are surrounded by the sea; but this, by know means, makes it one of the prettiest. I have seen far more towns in my travels that beat out Greenport, NY hands down.

    Also, behind the veneer of the main street, you will find the other side of Greenport, NY most do not see, the alcoholics, drug addicts, and a slew of other ugly problems.

    Greenport, NY is far from being one of the prettiest towns in America.

  • shelty 3 months ago

    Right On!

  • smithlc2 3 months ago

    Thank you for highlighting Charlevoix as one of America’s Prettiest Towns! One correction: Round Lake is the harbor lake the town overlooks. This “isthmus” sits between Lake Michigan and Lake Charlevoix.

    Charlevoix is a wonderful place to live and visit. In the summer there is no end to outdoor sports including boating, sailing, swimming, fishing, biking, tennis, and golf. The town has abundant shopping and dining, as well as galleries and a vibrant art center. From downtown you can walk to three completely different kinds of beaches. In the winter there is skiing and skating and other winter sports.

    You are correct that the highlight of the summer is the lighted boat parade and two nights of fireworks for the Venetian Festival, and the juried Art Fair is legendary, but there’s something going on almost every weekend! During the week, you can enjoy the town band in the pavilion on the water, or jazz in the gardens outside the town’s fabulous library. You can also tour a restored fairytale stone castle, which hosts over a hundred weddings a year, and hobbit-like Earl Young stone cottages are sprinkled about the town.

    If you are looking for a great place to visit or settle down, you can’t go wrong with “Charlevoix the Beautiful!”

    Larry Smith

  • billprescott 3 months ago

    Ferndale is a beautiful town in the Humboldt Redwoods. Thanks for mentioning this hidden gem behind the Redwood Curtain. To see some pictures of local Ferndale business go to


  • brooklynpaul 3 months ago

    I disagree with your disagreement. Maybe as a local you are too close to see it. I’ve been spending Spring/Summer/Fall weekends in Greenport for 5 years now. Its a great town. Nothing better on a Summer Saturday then to walk the piers and the town streets. Its alive, and fun, and…pretty.

  • bstaffel21 3 months ago

    I am fortunate to be living in Charlevoix. I always felt that this was the perfect vacation spot, no need to go anywhere else to enjoy a vacation. We have four seasons with fun for all four, a number of delightful restaurants. The marina is full of yachts, big and small during the sailing months and always a delightful sight. The Waterfront Art Fair is the place to go in August, but there are other events throughout the summer season especially. Hope you come up to this wonderful place. As an artist/potter, I have found my “heaven.”

  • alexandrastillman 3 months ago

    The Redwood Country has several lovely small towns. Eureka has the most intact historic homes than anywhere in the US. Arcata has the last Plaza in California and its very own Redwood Park which can be seen from Arcata Stay’s Plaza View accommodations. Arcata’s Redwood Park has many trails leading into the Redwoods for hiking, walking and biking.