Just like any other person at the beginning of the week, I opened my Facebook feed to catch up on the stuff I missed over the weekend.

What I found instead was a dated article that chose the "prettiest towns" in each state. The article came from Architectural Digest and highlighted whatever town had a combination of pretty architecture and an abundance of nature, with bonus points to towns with history embedded in its buildings.

Starting from the top of New England:


Architectural Digest had Stonington, Maine, as the prettiest town. The article said that visiting the fishing village of Stonington was like "slipping back into time, with wooden boats bobbing in Penobscot Bay and homes (many with cedar-shake shingles) built into the sloping hillside."

I think there are at least two towns I would say have a slight edge over Stonington; however, Stonington is a cute top three choice.

Regarding the prettiest town in Maine, my gut says Bar Harbor. Perhaps I am biased, as I am a nature lover. Bar Harbor is a perfect getaway, and encompasses what I think "Vacationland" is all about.

Getty Images
Getty Images

Downtown Bar Harbor is adorable. It has endless shopping and eating options, you can stay in very quaint hotels and motels, and it's minutes from Acadia National Park. Between the downtown and Acadia, Bar Harbor holds #1 in my heart.

Getty Images
Getty Images

I would not be surprised to see Ogunquit hold the #1 spot in Maine for others. For me, it ranks 2-3. The town's motto is “Beautiful Place by the Sea.” This motto holds true if you have ever been. Ogunquit has a very friendly downtown, 3.5 miles of gorgeous beach, and a lot of history like the famous Ogunquit Playhouse.


Architectural Digest had Stowe, Vermont, as the prettiest town in Vermont, and I won't disagree too much. Stowe is gorgeous. It is tucked away from the busy Burlington, and is a small town nestled around the peaks of Stowe Mountain Resort.

Aerial view of fall foliage, Stowe, Vermont, USA
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There is a lot of competition in Vermont for "prettiest town." From the United States' smallest capital, Montpelier, to the ever so charming Woodstock, there are many choices that could take the cake.

Other than Woodstock, I would say that perhaps Shelburne could have a go at #1. Shelburne is right on the incredible Lake Champlain and one of Burlington's suburbs. Because of its proximity to Burly and Lake Champlain while retaining the small town feel, I could see Shelburne at #1.

Google Maps
Google Maps

I am content with Stowe taking the crown.

New Hampshire

I am very pleased with Architectural Digest's choice of New Hampshire's most pretty town: Portsmouth. I agree.

Portsmouth, New Hampshire, USA town cityscape.
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There is not much else to say. Portsmouth is right on the water, has an immense amount of history, and still holds a charming yet modern look. There are so many choices for food and drink in Portsmouth. You could spend weeks here and still miss out on the best local beers and food.

The only other place in New Hampshire I would put in the running would be North Conway. Everyone remembers their first trip up north: stopping at Zeb's for some candy or vintage toys, hoping on the Polar Express, or just shopping in Conway's downtown strip overlooked by Cranmore.


According to Architectural Digest, the prettiest town in MA is Edgartown, Massachusetts.

"This former whaling port of about 5,000 residents—located on Martha’s Vineyard—includes two lighthouses (Cape Pogue Light and Edgartown Harbor Light) and a gorgeous shoreline," says Architectural Digest.

Born and raised on the North Shore, my bias wants me to discuss Newburyport for the cute downtown and views of where the Merrimack River meets the ocean. That said, there are a few other towns that must come before Newburyport, and perhaps Edgartown.

I think those who live or frequently visit either Provincetown, Nantucket, or anywhere near the South Shore would argue that their own town could claim the #1 spot. I would also say all towns probably have valid arguments to be the most beautiful in Massachusetts. P-Town and Nantucket are great choices as they offer stunning beaches, cute New England charm, and often great nightlife.

Nantucket And Martha's Vineyard Struggle With Tourism Due To COVID-19
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Since the traffic getting there and driving while on the Cape, Martha's Vineyard, or Nantucket is almost as bad as Long Island...if commuting was a factor, I would go back to my Newburyport selection or even Rockport.

Connecticut and Rhode Island

I completely agree with Architectural Digest for their choices of the prettiest towns in Connecticut and Rhode Island.

When thinking of Connecticut I always think of Mystic. I have spent time in Mystic for no other reason other than that I like the area. It checks off many boxes of what makes a New England town cute: close to the water, good restaurants, breweries/beer gardens nearby, and the casinos being driving distance works out, too.

As for Rhode Island, I have only spent a small amount of time there. One of the times I went, I visited "Block Island," Architectural Digest's choice. Not knowing much else about the state, I will say it was a pretty place with 17 miles of beaches, and exactly what you would expect when taking a ferry to an island in New England.

What do you think? Were Architectural Digest's choices accurate? What do the locals say about the prettiest town in each New England state?

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