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

“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?”

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!

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).

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.

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.)

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.”)

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.”

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?

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!