Oaks Bluff
Marthas Vineyard

Adventure on the vineyard

As a military family stationed in Massachusetts, it only makes sense that our first summer trip here lead us to Oaks Bluff Marthas Vineyard! We probably visited the vineyard before having all of our boxes unpacked. It is a completely separate island off the coast of Cape Cod. We arrived to the island by ferry from Woods Hole, MA. The ferry ride, although crowded in the midst of the summer, was a worthy picturesque ride. Our toddler loved the open water views.

Oaks Bluff Marthas Vineyard

After about 45 minutes on board, we arrived at the Oaks Bluff port. Believe it or not, the vineyard actually consists of several towns and has an approximate population of 16,000. We chose to visit Oaks Bluff to view its’:

  • Unique cottages
  • Boutiques
  • Pristine beaches
  • Jaws Bridge
  • Americas oldest carousel (We will get to that!)

Stepping off the ferry, you are completely immersed in the culture. You just feel it. You literally get this unexpected, lush island vibe. Walking through the streets or alley ways, music is blaring and tropical scents are robust. As far as the tourists, like ourselves, there were countless types of human interaction. Families, singles, photographers, fisherman, etc. You name it, they were there.

First Stop

Our first stop, Andersons bike rentals! Yes, we hopped on bicycles with a child trailer for our toddler and took off. Destination: the infamous jaws bridge. Jaws bridge, as you can imagine, was named after the filming of Jaws in 1975. Although the ride was absolutely charming and memorable, it certainly wasn’t easy. The ride was a good 3.2 miles (one way) on a rental bicycle. Not so comfy for the tush, but totally worth it. (Isn’t it funny; the particularly funny moments you recall from a travel experience?) 

Along the way, beautiful beaches were to our left. Furthermore, farmland and lush grass were on the right. During most of the trek, a wide pathway is available for bikers and such. Riding up to the bridge was extremely obvious as you witness bodies jumping off the ledge. There IS a sign that states ‘No Jumping Off Bridge.’ However; this didn’t seem to phase any of the beachgoers. We learned that the rule isn’t taken quite so seriously as it is deemed a vineyard “rite of passage.” 

Jaws Bridge

We got settled on the beach, just next to the bridge to see the action. The sun was shining and island music played in the background. Our son was a little groggy from his nap inside of the baby bike trailer. Once he realized he could splash his toes in the water and build a sand castle, he was back to his energetic self. His smile and adorable swimsuit butt makes the memory that much more special. These pictures are certainly some of our all-time favorites. 



In the center of town you’ll most likely pass by the famous Flying Horses. It is Americas Oldest Carousel! As a very neat attraction to witness, this carousel is known for first being located in New York City in the 1800’s. It was then transferred to the vineyard! We walked around town, visited small boutiques and grabbed some lunch. Our last stop; an ice cream parlor (of course). Our toddler was totally pooped at this point, but couldn’t resist the messy ice cream smile! 

Oaks Bluff Marthas Vineyard was a great experience and we certainly plan to go back and see other areas! Hard to imagine how extensively large it is. Next time, we will visit the other side of the island! If any readers have been, please reach out or leave a comment below. I would love to hear of other travelers experiences! 

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