“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!

The author, Lillie Marshall, is a 6-foot-tall National Board Certified Teacher of English, fitness fan, and mother of two who has been a public school educator since 2003. She launched Around the World “L” Travel and Life Blog in 2009, and over 4.2 million readers have now visited this site. Lillie also runs TeachingTraveling.com and DrawingsOf.com. Subscribe to her monthly newsletter, and follow @WorldLillie on social media!
Carrie
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
Lillie
Monday 30th of October 2017
Thanks for the tip!
Christy
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.
Lillie
Wednesday 28th of September 2016
I had no idea they did that at night! I'd love to see it. Thanks for the tip!