Explore: Gingerbread Houses

I know it's not nice to play favorites, but the gingerbread houses in Oak Bluffs are absolutely my favorite attraction on Martha's Vineyard. The first time I ever came to the island I was in middle school. I don't remember many details of that trip, but I do have really strong memories of walking around, wide eyed, through the rings of gingerbread houses. 

Over Labor Day weekend I got the chance to visit the houses again. My travel buddy and I took the 12pm ferry to Oak Bluffs. After a spin on the Flying Horses Carousel and a good hour of bopping in and out of the shops on Circuit Avenue, we headed for the gingerbread houses. 

We entered through a tiny side street, right across from the Vineyard Vines store. 

Martha's Vineyard Gingerbread Houses

The sun was shining, putting the incredible details of each house in the spotlight. 

Martha's Vineyard Gingerbread Houses

I was swooning over so many of these porches. I could easily picture myself sitting out there with a book and an ice tea, watching the world go by. 

Martha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread Houses

Some of the porches had very sweet details, like the hearts on this deck. 

Martha's Vineyard Gingerbread Houses

Speaking of hearts, this cottage is called Summer Love and you can't help but smile when you see it. 

Martha's Vineyard Gingerbread Houses

I love the row of hearts on the base boards of the porch. 

Martha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread Houses

And don't even get me started on this adorable gate! 

Martha's Vineyard Gingerbread Houses

Summer Love was the first of many pink houses we would see that afternoon. 

Martha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread Houses

This cottage reminded me of Barbie's dream house. Check out that chandelier! 

Martha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread Houses

This blush pink house was a bit run down, but I loved its dog house sign. 

Martha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread Houses

As we continued wandering, we started noticing all the homes with balconies on the second floor. They looked like the most private and peaceful hideaways. 

Martha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread Houses

As we turned a corner, we spied a house that looked like the American flag personified. 

Martha's Vineyard Gingerbread Houses

I was positively giddy to discover the Wizard of Oz house! 

Martha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread Houses

I only noticed the film title painted above the front door, but my friend spotted all of the main characters poking out of the plants in the front garden! If you visit with kids, challenge them to find all four characters among the flowers. 

Martha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread Houses

I have to admit, we almost didn't find the Scarecrow. He was really tucked in there! 

I could have kept meandering in between the gingerbread houses all day. Each time I looked at a house, I noticed a new small detail. 

Martha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread HousesMartha's Vineyard Gingerbread Houses

We ended our exploration on the back side of the Cottage Museum, which is home to the gift shop. 

Martha's Vineyard Gingerbread Houses

The shop has wonderful postcards, note cards, magnets, Christmas ornaments and more. I couldn't resist a water color painting of the Summer Love cottage. I will smile every time I look at it! 

As we walked back toward Circuit Avenue I had a spring in my step. It's impossible to walk through the gingerbread houses and not feel a child-like sense of wonder. 

Tell me, have you visited the gingerbread houses? Do you have a favorite cottage? 

Comments

Kristen Fenton's picture

these houses make me so happy!

Molly's picture

Me too! You cannot help but smile the entire time you are wandering around.

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Molly Galler

Welcome to Pop.Bop.Shop. My name is Molly. I’m a foodie, fashionista, pop culture addict and serious travel junkie. I’m a lifelong Bostonian obsessed with frozen confections, outdoor patios, Mindy Kaling, reality television, awards shows, tropical vacations, snail mail and my birthday.

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Gingerbread Houses
1 Trinity Park
02557 Oak Bluffs , MA
United States
Massachusetts US