My Bucket List, or Day Trip to Oak Bluffs on Marthas Vineyard

I recently ran into a gaggle of women of a certain age from Ohio on the streets of Woods Hole.  They were wearing matching yellow t-shirts which were titled “My Bucket List” and included Las Vegas, New York City and you guessed it, Martha’s Vineyard.  I hear this a lot at the front desk of the inn: “We are headed over to Martha’s Vineyard — it’s on our bucket list!”  It might surprise you to know that Vineyarders never refer to their island home using the full name — they call it “the Island” or sometimes “the Rock.”

Summer keeps me pretty darn busy, but yesterday dawned clear and warm — one of the most beautiful days of September — and I hopped the ferry to get on the Rock.  The boat leaves about 50 yards from the front door of the Woods Hole Inn, and I walked on with other passengers up the ramp to the left of the terminal (round trip $16).  The 45 minute trip across Vineyard Sound was uneventful, just lovely views over Nobska Lighthouse, West Chop, Vineyard Haven with gulls circling above, tourists posing for pictures.

The Oak Bluffs ferry landing is offered in summer only, and this was one of the last days one can ride directly to “OB” as the locals call it.  By the time we pulled into the slip, the wind and waves made the landing challenging and I heard that later ferries were diverted into Vineyard Haven which is a much more protected harbor.

In Oak Bluffs, I met an old friend from high school and we wandered down to the harbor looking for a great spot to eat.

We found it on the second floor deck of a gingerbread cottage turned restaurant called “Lobsterville,” where we sat in the sun overlooking the harbor and enjoyed a delightful meal.  Catching up with old friends in this kind of venue is unique — you want to talk about the last thirty years, but there are so many interesting things to look at and see that sometimes the conversation gets derailed, like Yes, then my father died oh look at that beautiful wooden sloop.  (Maybe those two thoughts are not so disconnected anyway.)

At Lobsterville, I ordered the steak appetizer on the recommendation of the waiter.  It came on a puff pastry with tomatoes and melted mozzarella.  It was enough for a full meal with two pieces of steak, a drizzle of reduced balsamic and this delightful sprig of rosemary ($16).

After lunch, we wandered the streets of Oak Bluffs past hamburger joints, moped rentals, t-shirt shops, fudge and candy stores and of course the famous 100+ year old “Flying Horses” Carousel.  We strolled into several wonderful Inns (the Dockside, a new place which looks super chic) and the Oak Bluffs Inn, a charmingly renovated authentic Victorian.

Oak Bluffs Inn owner Eric showed us the tower atop his building with wonderful views of Circuit Avenue and the ocean in the distance.  He was really nice, taking time out of a busy day to give us a full tour.  Here is a webcam of the view from this tower!

We also strolled the Campgrounds, also known as the Gingerbread Cottages.  This unique community of 1880’s miniature Victorian houses circles around an open air wooden meeting hall which was used for Methodist Revival Retreats back in the day but now is a gathering place for summer concerts, lectures and other cool things like a summer taping of the “Moth Radio Hour.”  Last year when I walked through the Campgrounds, Wynton Marsalis was playing.   This is hallowed ground, a national landmark and one of the most charming neighborhoods you will ever visit.  It is a very short walk from the ferry.

On the way back to Woods Hole, I managed to get a photo of the new Quicks Hole Tavern (our new year round restaurant opposite the ferry) which was a new angle on the building, especially photogenic on this lovely blue sky day before the leaves start to turn.

Back in Woods Hole that evening, a local band called “Brother’s Rye” was playing in front of Quicks Hole Taqueria and le tout Woods Hole was out on the streets to enjoy the last gasp of summer weather.

As the day ended, I thought about the nature of friendship and travel, that I can get away to this incredible island next door,  pick up a conversation with an old friend from the tenth grade, enjoy the crisp, clear fall weather on Cape Cod, and return home to my friendly village with music placing in the streets.

I don’t have a bucket list, but if I did, my day trip from Woods Hole to Oak Bluffs (aka The Rock) would most definitely be on it!