Note: The Kelley House, hosted our stay and dinner at The Newes from America Pub, as always, all opinions are my own. 
Naturally our first order of business for day 2 on Martha’s Vineyard was to head to the lobby for coffee, and then to take in the devastatingly beautiful view of Edgartown Harbor from our balcony at the Kelley House. After sipping, reading the local paper, and trying to memorize the view to take with us forever, it was time for breakfast!
We headed down the street to the Edgartown Diner, a year-round Edgartown favorite, which a friend had told me about. Walking in, the spotless diner was truly reminiscent of the Joanie loves Chachi days, and who doesn’t love a sock-hop vibe?!
The food was delicious, using local and high quality ingredients, but the real story here was our incredibly friendly and patient waitress, Esther, who just reinforced what we already knew: People who live on an island like Martha’s Vineyard are just happier! 
After breakfast we decided to take out a couple of the bikes the Kelley House has for guests (and non-guests can rent them too) for the picturesque 6 mile ride to Oak Bluffs. The day was much hotter than we expected, and it felt more like Spring than Fall, but who are we to complain that the weather was too beautiful?! 
We made our way along to water and arrived in historic Oak Bluffs. We locked up the bikes, and strolled through the streets making sure to stop at pretty much the cutest Vineyard Vines store ever. 
We then strolled through the famous and whimsical gingerbread cottages picking out our favorites and imagining what it would have been like to live there in the mid 1800’s. 
It was time to hop back on our bikes and head back to Edgartown. But before we got back to town, we were stopped in our tracks by a local brewery open for the last week of its season…to be continued.
I’ve never been to Marthas Vineyard but you really make it look good. I love your photo of the Gingerbread Cottages too. What a destination!