October 22-26, 2009 - Martha’s Vineyard & Boston, Massachusetts

My friend Kylee and I met in Boston on this weekend.  On our first night we went into town and ate dinner at Legal Sea Food, which was great!  On our second day we drove to Woods Hole, MA to catch the 45-minute ferry to Martha’s Vineyard.  We checked into our hotel, the Madison Inn, in the Oak Bluffs area.  

We had fun exploring the island over the next 2 days.  Being off-season, the island practically felt desert in a lot of areas.  About half the shops were closed, and there were only a handful of restaurants open.  But we absolutely loved it.  A lot of times on a vacation I like to get the sense of what it is like to just live somewhere…not necessarily be a tourist.  And this was a perfect opportunity for a trip like that, because it was pretty much just locals left on the island.

One thing we did not prepare well for was how cold the weekend would be!  We were just freezing; so on our first afternoon I found a shop that sold these great knee high wool socks.  They were a lifesaver!  As you can see – I had to feature them in one of my feet pictures at Gay Head Cliffs.  

We figured out the bus system pretty easily to get around the island.  In Oak Bluffs we were able to walk up and down the boardwalk, walk along the beach (so deserted and peaceful), and we saw the gingerbread houses.  In Vineyard Haven we walked around the various shops that were open and explored some of the town highlights.  On our second day we took the bus out to the Aquinnah Cliffs (Gay Head Cliffs).  The view was spectacular from up there, but boy was it cold and windy!  We didn’t realize in the off-season the buses came so infrequently, and we ended up stuck there for over 2 hours.  We went in a few of the shops, looked at the lighthouse and grabbed some apple cider to warm up.  Then we ended up huddled in a doorway of a closed shop to block the wind until our bus came back.  

We finally caught our bus and took it to Edgartown.  We ate lunch at The Wharf, explored some of the shops and then walked to see a lighthouse.  At first it was just sprinkling, but then it full out poured on us!  Thankfully Kylee had bought a jacket for her husband, so I threw that on to stay somewhat dry.  After that we finally caught our bus back to Oak Bluffs, got out of our wet clothes and relaxed.

One of our favorite memories of Martha’s Vineyard was the restaurant – Offshore Ale Co.  As I mentioned not much was open that time of year, and we actually ended up eating at this same restaurant for lunch and both dinners. It was jam-packed every night, but it was just a great place all around.  Met some very friendly people, enjoyed one of their beers and had the most amazing Lobster Roll for dinner – that we still crave to this day!  

On day 3, we took the ferry back to the mainland.  I drove Kylee to the airport, and then I had the rest of the afternoon to quickly explore Boston.  I walked down to the Charles River, and then headed over to the Cheers bar.  I sat in the Boston Common Park to eat some late lunch.  Then I found the start of the Freedom Trail and I followed the path from the State House all the way to the Copps Hill Burial Ground.  I walked through the Old Gramary Burial Ground and the Holocaust memorial.  Then I finally called it a day and took the subway back to my hotel.  Grabbed some dinner and got some sleep before my early flight home the next day.

Check out some more photos from this trip here - Martha's Vineyard & Boston Photos