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Martha’s Vineyard’s Gingerbread Cottages Are So Cool!

The middle one really looks like a gingerbread house.
The Gingerbread Houses of Oak Bluffs, Massachusetts are not to be missed.

“Lillie, do NOT leave Martha’s Vineyard without tracking down the Gingerbread Houses!” typed one of my readers on my Facebook wall.

“Gingerbread Houses?” I muttered to myself. “What the heck is this woman talking about?”

This white one reminds me of icing, or temples in Chiang Mai, Thailand.
This white cottage reminds me of icing, or temples in Chiang Mai, Thailand.

A few minutes of Internet sleuthing later (during which time my baby spit up all over my husband’s shirt) revealed that a major tourist attraction of Martha’s Vineyard, Massachusetts is a cluster of fairy-like wooden houses in the town of Oak Bluffs which are known as “Gingerbread Houses” or “Gingerbread Cottages,” depending which website you go by. We packed up our hotel room (click to see the Martha’s Vineyard hotel we loved) and hopped in the car to find the gingerbread!

Love the pink houses best!
I love the pink Gingerbread Houses best!

Gazing at these photos, its easy to see how these houses got nicknamed “Gingerbread.” They are slathered with bright colors like sugar-saturated food coloring, and garnished with curls of wood mimicking the wisps of icing you long to snap off of real gingerbread houses and shove into your mouth (though you know your mother would catch you and scold).

Each one of the Gingerbread Houses is different.
Each one of the Gingerbread Cottages is different.

So what is the history of these luscious confections of architecture? In the late 1800s, Methodists gathered in Oak Bluffs each summer for religious meetings. As the years went by, they began erecting petite wooden houses instead of tents, and started to try to outdo each other in how ornate they could make each cottage. The style they perfected is now known as “Carpenter’s Gothic,” (a name which makes me smile) due to its fancy-schmancy wooden frills.

I love the curly wood decorations hanging off every roof!
I love the curly wood decorations hanging off every roof!

Now, dear traveler, actually locating these delightful houses is harder than I thought. Merely plugging “Gingerbread Houses, Oak Bluffs” into my smartphone’s map app yielded nothing. Finally after extensive asking and Googling around, we stumbled upon all of these awesome houses on Clinton Avenue: a car-free strip of greenery snuggled against a labyrinthine series of concentric circular roads. (Did we end up lost and going around and around those circles? Yes, sir.)

And this one looks so much like a gingerbread house I might eat it.
This cottage looks so much like an actual gingerbread house, I might eat it.

Another word to the wise traveler: I would suggest visiting these wooden beauties at mid-day or before. If you notice, half of my photos here are vibrantly colored (ex: above), and the other half have that washed-out quality sadly present in pictures taken into the sun (ex: below).

I wished we had come when the sun was either above-head or on the other side on the road, since the side the sun was muddling actually had the cooler houses. (No offense, other side, but you can’t beat a neon pink cutie entitled “La Vie en Rose.”)

Brightly colored, ornate wooden houses? Yes please!
Brightly colored, ornate wooden houses? Yes please! This one has the title, “La Vie en Rose.”

Now, let us pull our focus back from Clinton Ave. and towards Oak Bluffs as a whole town. Happily, charming and whimsically styled architecture like these Gingerbread Cottages punctuates the entire beach-side town. Further, Oak Bluffs has the honor of being the hot summer spot for wealthy African-Americans, boasting Black elites such as Harvard professors, doctors, CEOs, and more each summer for the past several decades, and earning Oak Bluffs the nickname, “The Black Hamptons.”

This gingerbread cottage looks like mint ice cream. Mmm...
This gingerbread cottage looks like mint ice cream. Mmm…

Of all the towns we visited on Martha’s Vineyard, Oak Bluffs was our favorite (besides the alpaca farm). What can I say? I’m ever seduced by bright colors and whimsey in architecture! It’s why I loved Willemstad, Curacao. So what about you? Do you like these houses? Which is your favorite?

I adore you, Gingerbread Cottages of Martha's Vineyard.
I adore you, Gingerbread Cottages of Martha’s Vineyard.

Did you know you can actually rent out and stay in many of these Gingerbread Cottages??? Use this affiliate link to click here to see one listing.

If you enjoyed this article and are still planning your trip, use this affiliate to click here for an easy link to Martha’s Vineyard hotel deals, and here for vacation rentals on Martha’s Vineyard, as it will give a small commission to help support this site at no extra cost to you. Happy travels!


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Friday 13th of March 2020

We had so much fun meandering around MV- it’s a chocolate box place for sure. I loved the quaint cinema and the ghost tour too!

Lillie Marshall

Friday 13th of March 2020

So many more parts of Martha's Vineyard that we have yet to explore!

Ajay Rastogi

Saturday 25th of January 2020

I’d love to see what the Gingerbreads hold inside. They are very unique blog post.

lori moose

Saturday 14th of September 2019

Thousand Island Park ( TIP ) is a beautiful little historical community on Wellesley Island in the 1000 Island region, we have over 300 Vicorian cottages its a beautiful magical place, check it out ! :) I would love to visit this place someday as well. Take care

Lillie Marshall

Sunday 15th of September 2019

Thanks for the tip! I'd never heard of it before.

Greta Macpherson

Saturday 28th of October 2017

if you love gingerbread houses, goggle Grimsby Beach, Ontario to see another great community.

lori moose

Saturday 14th of September 2019

Have you been to Thousand Island Park NY ? A gorgeous Victorian Cottage community in the 1000 Islands


Monday 30th of October 2017

Thanks for the tip!


Wednesday 28th of September 2016

Illumination night is magical. They have hundreds of lit paper lanterns hung all over the porches. Crowds of people go to walk around and admire the beauty of the houses and the lanterns.


Wednesday 28th of September 2016

I had no idea they did that at night! I'd love to see it. Thanks for the tip!

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