THT- Martha’s Vineyard Trip Part II - Elegantly Dressed and Stylish
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THT- Martha’s Vineyard Trip Part II

Yesterday I shared Part I of our trip to Martha’s Vineyard, today is part 2.

Martha’s Vineyard Trip part 2

I mentioned yesterday, that this was our first trip to the “Vineyard” as it was highly recommended by family. It was also a bit of a test for me, with my PN, to see how I would be able to travel after 10 months of PT, and adhering to a pt home program.

We would fly to Boston, take a bus to the ferry, and catch it to the Vineyards, stopping at Vineyard Haven, one of the towns in Martha’s Vineyard. Each place has its own character.

Let me say that I wore about 1/3 of what I packed, and I was so glad I packed sweaters in mid May. It was a bit chilly, but I wore mostly the sweaters and longer sleeve CSW tops with CSW pants. Sneakers were a must, except when we went to dinner and I brought one other pair of dress shoes.

Historical Walking Tour ( Carnegie ) Edgartown

One of the first things we did was go on a walking tour to narrated by a woman from the Carnegie Heritage Center 

run by the Vineyard Preservation Trust. This was a gift from Andrew Carnegie, and has been a library, cultural center, and museum.

“Inside offers a a dynamic revolving exhibit, Living Landmarks, which illustrates the historical development of Martha’s Vineyard through the lens of the landmarks in Vineyard Preservation Trust’s care.”

Their goals are to preserve and maintain historic buildings and the integrity of places on the island, as well as to inform. The tour was very interesting, and one of the places we saw was an old Whaling Church. 

Recent artist painting 3d artwork to replicate the old church’s interior.




“​One of New England’s most elegant com­munities, Edgartown was the Island’s first colonial settlement and it has been the county seat since 1642.The stately white Greek Revival homes built by the whaling captains have been carefully maintained. They make the town a museum-piece community, a seaport village preserved from the early 19th century. Main Street is a picture-book setting with its harbor and waterfront.”

This is where we stayed. It was close to everything, and we took the public buses to the neighboring towns, which was much easier than renting a car, or bringing ours. It is a charming town, with quaint shops, amazing restaurants,  historic landmarks, and beaches ( which were too cold to go to now).

I shared the Lightkeepers Inn, in Edgartown, which we stayed, in yesterday’s POST. We also saw the Edgartown lighthouse.

The Lightkeepers Inn – Where we stayed – you can see the inside of our room in yesterday’s post.

Listened to a Blues band with a 25 year old female guitarist. I even texted my sister that I was out at 11 pm! 🙂

The oldest Pagoda tree

Vineyard Haven

When ships were powered by wind and sail, Vineyard Haven was one of the busiest ports. There is much history to these whaling villages, and I could go on, but if you are interested, THIS SITE, is excellent for more historical information. Great restaurants, hotels, inn, shops and views of the water. The earliest English settlement dates back to the 1600s.

Oak Bluffs

The charm and down to earth charisma of Oak Bluffs won our hearts. “Oak Bluffs is also the home of the Flying Horses Carousel, the oldest continuously operating carousel in the country. Its horses were hand-carved in New York City in 1876” credit  We did see the Carousel, but it was being renovated and unvieled on Memorial Day week, so I couldn’t go on it .

We visited a bar in the evening called, The Ritz. It was a small islander, neighborhood bar. I tend to like the smaller ones that have character and are cozy. There was a rock band playing that are regulars on the MV scene. We spoke most of the evening to a local fisherman, Mark, who said he was ready to retire. As the redness spread to his face, he offered to buy us Green Tea shots, a mixture of Jameson and Peach Schnapps. Let’s just say we slept well that night, but I love hearing stories from locals.

Aquinna/Fishing Village of Menemsha

“​Many year-round residents of Aquinnah are descendants of the Wampanoag tribal members who showed the colonial settlers how to kill whales, plant corn, and find clay for the early brickyards. Much later, these Aquinnah Wampanoaq were in great demand as boatsteerers in the whaling fleets.”

There are a small amount of people who live on Menemsha/Aquinna, and we saw the fishing village. Since we ate some hearty lobster rolls, we were too full to eat there. But talk about fresh, the fish practically leap onto your plate!

Here is where we saw the Gay Head lighthouse, the only operating lighthouse left on MV and the Aquinna Cliffs, which were so picturesque, they didn’t seem real. The lighthouse was actually moved, as it was getting to close to the cliffs, and they were fearful it would collapse. We watched a time lapse video in the museum of this lengthly task.

Where the lighthouse was originally near the cliffs, and where it was moved.

The Cliffs

Food- Oh How we Ate Well

Can’t get enough clam chowda

The Lookout voted the BEST lobster rolls in MV. Hubby has his hot with butter, mine was cold with light mayo. Soooo good!

Gingerbread Houses at Oak Bluffs

The trip is nearly over and we are on our way back to our Boston hotel. Let’s just say it was a bit windy!

It was a great trip and I really needed a change of scenery!

Don’t forget, you can read about PART 1 OF OUR MARTHA’S VINEYARD TRIP HERE.

Have a great week!

Jess xx



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  • Maureen
    Posted at 15:48h, 07 June Reply

    What a fun trip with so many great sights and history. I love places like that! It just makes traveling there much more interesting. The food there looks amazing too and the only soup I cannot get enough of is clam chowder. It is my favorite! Yum. And how cute are those gingerbread houses! Love it. Definitely adding Martha’s Vineyard to my travel bucket list!

    Maureen |

  • Joanne
    Posted at 14:31h, 07 June Reply

    Oh yes “chowdah and lobstah rolls” are a must when near the coast! It sounds like you had a wonderful time.

  • Veldene Bergen
    Posted at 14:35h, 06 June Reply

    Great article! I clicked on yesterday’s as well so I got the whole trip. Glad you posted this as my hubby really wants to take me to Boston, so it’s nice to see some additional areas we could check out.

    • Jess Jannenga
      Posted at 10:08h, 09 June Reply

      I bet you would have a great time! We didn’t have time for Boston, as it was mainly a MV trip, but I would go back to check it Boston as well.

  • Leslie Susan Clingan
    Posted at 22:04h, 04 June Reply

    I am so proud of you!! Staying up late, meandering about like a tourist. Sounds like you really lived it up. Good for you. Hope you’ve been able to rest up now that you are home. But what a picturesque place to vacation. I think I must have visited the vineyard when I was a child but I don’t remember. The houses, the view from the dock, looking out at the boats could be scenes from a century ago. Like stepping back in time.

    And the food. Just finished dinner over here but if I could slurp down that bowl of chowda, I surely would.

  • Hilda Smith
    Posted at 13:50h, 04 June Reply

    Oh Jess what an interesting trip and that food is right up my street. I enjoyed Martha’s Vineyard vicariously through you. xxx

  • Kellyann Rohr
    Posted at 13:38h, 04 June Reply

    Sorry I missed the link up! So happy to see this post though. Everything looks so quaint and charming. Give me a lobster roll any day of the week!

  • Silkworth Melanie
    Posted at 08:15h, 04 June Reply

    My kind of getaway! I haven’t been to Martha’s Vineyard yet, but on my list. Thanks for sharing!

  • Emma Peach
    Posted at 19:11h, 03 June Reply

    Those houses are so pretty! What a charming place! I usually only wear a third of the clothes I take on holiday too!

    Emma xxx

  • Michelle
    Posted at 13:17h, 03 June Reply

    Nothing better than live music! And it’s so fun to see how other people, and what is important to them. Those ginger bread houses are so adorable! The different colors remind me of the Victorians in the San Francisco Bay Area.


  • Nipa | Fashionipa
    Posted at 14:19h, 02 June Reply

    So glad to hear that you were able to get away! Looks like a beautiful and delicious break! Xo Nipa

  • Michele
    Posted at 16:14h, 31 May Reply

    OK, so first I laughed so hard when you said you let your sister know you were out at 11 pm! Remember when we wouldn’t go out until 11!! Then when you shared that you ate well (my comment on part 1!!) It looks so fantastic there-love the gingerbread houses and the cliff! Definitely going on ly list of where to travel!


  • Gail
    Posted at 01:30h, 31 May Reply

    So glad your long awaited holiday went well. I’ve always been intrigued to see Martha’s Vineyard. The food looks wonderful! xx

  • jodie
    Posted at 18:24h, 30 May Reply

    Those walking tours are the best. That’s what we always like to do because you learn so much.
    The food looks fabulous, and good thing you took sweaters and layers.

  • Jill
    Posted at 17:47h, 30 May Reply

    I’ve always wanted to spend a weekend in Martha’s Vineyard. It looks so quaint, and that lobster roll is calling my name!

    Jill – Doused in Pink

  • Rena
    Posted at 15:59h, 30 May Reply

    Thank you for sharing these fabulous photos and the details of your trip.


  • Di
    Posted at 15:44h, 30 May Reply

    Oh my, Martha’s Vineyard and these little towns are so beautiful and quaint! The food looks fabulous, too. Glad you had such a wonderful and memorable trip. Thanks for sharing with us!

  • Carrie @ Curly Crafty Mom
    Posted at 13:55h, 30 May Reply

    Wow! I would have loved this trip. I really love lighthouses and I’ve only seen them in Florida. The food looks REALLY good (and fresh!) and I love those gingerbread houses. Wow, I may have to add this to one of my places to visit someday.


  • Jennifer
    Posted at 11:24h, 30 May Reply

    Looks like an amazing time!


  • mireille
    Posted at 08:47h, 30 May Reply

    I love those pretty cottages! My favorite part of traveling without kids is the food! With them, we don’t tend to go out as much as it becomes too expensive!

  • Mica Away From The Blue
    Posted at 07:54h, 30 May Reply

    It looks like a lovely place to visit – you saw a lot of nice things and that food does look so good! Thanks for sharing 🙂 and thank you for the link up!

  • Susan
    Posted at 06:40h, 30 May Reply

    Jess it looks wonderful, we visited the island on a road trip in New England, so scenic and beautiful.

  • Jacqui Berry
    Posted at 02:54h, 30 May Reply

    Sounds like a marvellous trip and good to hear all about another part of the world. The food looks delicious too. Thanks for hosting Jess Jacqui.

  • Nancy
    Posted at 02:05h, 30 May Reply

    It looks like a lovely place! And the food looks delicious. I’m going to read your yesterday’s post as I also want to know where the name came from.

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