A True Vineyard Day

I just spent the weekend on our favourite island. It was fantastic. Of course, it was. When I arrived on Friday it was raining, but I was so happy to be there, that I didn’t mind at all. Besides, it wasn’t raining hard and I had dinner with great friends at The Port Hunter. That more than made up for it. Sunday it rained pretty heavily, but I spent a good chunk of it with one of my best friends, so again, I couldn’t have cared less about what the weather was doing. We went to that new spot, The Town, and we had a great time. Monday morning was beautiful. Saturday, though, Saturday was a “True Vineyard Day” to quote my friend Cynthia Riggs. Saturday was what life is all about on the island. So, today, I’m writing about a day on Martha’s Vineyard. It’s as simple as that. If the Vineyard touches your soul, you’ll know exactly what I’m talking about, and if you’ve never been, here is a taste of what you can expect…

Rise And Shine!

Literally! I woke up in my room, The Americana Room, at 1720 House in Vineyard Haven and I could see the sun cresting the horizon. I could tell it was going to be a True Vineyard Day. Normally, I am out before dawn with my camera, but this trip was half work and half convalescence. I really needed to catch up on my sleep. Thankfully, my bed and pillows were perfect, and the 1720 House is in a quiet spot. I slept like a rock every night. But once I’m up, I’m up! I got dressed and headed to The Black Dog Tavern for breakfast.

The Black dog Tavern

My favourite breakfast view

The Black Dog is my favourite place to have breakfast on Martha’s Vineyard. Of course, if you’ve been following my writing career at all, you already know this. My characters eat there a lot in my Martha’s Vineyard Mysteries. I like to live vicariously through them. Can you get food elsewhere that is equally delicious? Yes, you can, but no other place is going to give me a great breakfast, surrounded by warm wood and Vineyard history, and a table with a view of the ocean and the ferries. The tavern is literally on the beach.

A True Vineyard Day

The walk along the beach is a big perk

Making it even better, the quickest way to get to The Black Dog Tavern from 1720 House is to walk along the beach. I don’t know about you, but when I’m on vacation, the more time that I can spend getting sand in my flip-flops, the better! The cold May water lapped at my feet more than once and I could not have relished it more.

The rest of the morning was spent drinking coffee and taking photos—hey, it’s what I do. Then, I went ‘home’ and showered and changed my clothes. I was meeting my friend, Lisa Belcastro, for lunch, but really, my day was just beginning.

Making The Most Out Of The Day

 When I was showered and fresh, ready to go, I headed out to Lisa’s. Conveniently enough, Lisa also lives in Vineyard Haven. I walked down Main Street, under the miraculous summer sun, across Five Corners, and past the Martha’s Vineyard Museum. I had actually planned to go to the museum on Saturday, but the forecast had been much gloomier. There was no way that I was spending a minute of this glorious day inside if it wasn’t necessary! Lisa met me just outside her house with one of her trademark Lisa Belcastro hugs. If everyone had a Lisa in their lives, the world would be a better place.

The Aquinnah Cliffs

My dear friend, Lisa Belcastro

We jumped in her Jeep and headed to lunch. Lisa, in her infinite wisdom, had suggested the Aquinnah Restaurant for lunch. If there is a better spot to enjoy a True Vineyard Day, I don’t know what it is! They were serving brunch until 3:00pm. I saw some people having brunch when we got there and, not surprisingly, it looked delicious, but I had other things in mind.

The drive to Aquinnah was everything that you would want it t0 be. Lisa and I laughed a lot and caught up on our various friends and families. As we got closer, we passed Chilmark Chocolates—a Martha’s Vineyard institution. Lisa said casually, “Oh, we should stop in there on our way back.”

I responded with, “Sure. I’ve never been.” I thought Lisa was going to drive us off the road!

“What?” she exclaimed. “What? How is it that you, of all people, have never been to Chilmark Chocolates??”

I told her, “I’ve heard excellent things, but I don’t drive a car, and they’re a little off the beaten path, and they keep odd hours. It just hasn’t worked out.”

Lisa shook her head. “Well, we’re definitely going on our way back. They’re closing this season! You have to go.” Of course, I was totally down with that. You know how much I like to do things on-island that I have yet to try!


Aquinnah never disappoints. If you find yourself experiencing a True Vineyard Day, then get thee to Aquinnah! There are a lot of wonderful places on Martha’s Vineyard to experience an outdoor meal—The Seafood Shanty, TacoMV, Nancy’s Restaurant, The Lookout—but none can offer the views that Aquinnah restaurant can. When I sit down on one of those turquoise benches and matching tables, any remnants of tension that were scurrying around deep in the bottom of my soul, are wiped away.

Aquinnah Restaurant

I took this while sitting at my table.

My breaths get deeper and my smile gets wider. The sun finds you at every angle. I almost always order the lobster roll with homemade chips, and this time was no different. Why would it be? This was my first lobster roll of the season! My first lobster roll of the season and I was eating it on a one hundred foot cliff, over-looking the Atlantic Ocean. I spread sunblock on my face and head, and felt better than I had in eight months.

Aquinnah lobster roll

My first lobster roll of the season!

The service at The Aquinnah Restaurant is always good. I don’t know where they get their staff, but they are always friendly and patient. They seem to appreciate exactly where they are at every moment. When I consider how many people there are on the planet, and how many of them will get to experience Martha’s Vineyard, I am so very grateful. I am a truly lucky man.

Well-sated, Lisa and I strolled from the restaurant to the lighthouse. I think it would be sacrilegious to go to Aquinnah and not stop at The Gay Head Lighthouse. Were we ever glad we did! We bumped into a group of African-American women who were on-island for the first time! They were part of a church group and they honoured us with a hymn. Their voices were inspirational. They brought tears to our eyes. These are the things that happen on-island, especially on a true vineyard day. You just never know.

Special Vineyard Treats

Already, I can feel my head and face heating up. I pulled out my phone and took a look in my “selfie camera”—I use it as a mirror—and sure enough, I’ve got a lot of colour. Lisa and I crank up The Beach Boys and hit the road! It was a feel-good moment. That promise of summer, that warmth of the sun, had us feeling like summer was truly right around the corner.

We pulled into the drive of Chilmark Chocolates and I stepped inside for the very first time. Chilmark Chocolates is a very special place and you realize it the moment you open the door. The aroma of chocolate is intoxicating, but that’s not what does it. There are a lot of places that smell like chocolate. Hell, I’ve purchased cereals that smell like chocolate.

The moment I opened the door, I was greeted by an individual behind the counter who offered me samples with one of the most genuine smiles I have ever seen. If I wasn’t already bursting at the seems with happiness, this gentleman would have done the job. The same could be said for everyone behind the counter. These people were clearly happy to be at work and doing the job they were doing. Chilmark Chocolates is known for making a point of hiring handicapped people. That kind of community outreach fills the world with a positive energy that benefits all involved. No one benefits more than the patrons. Chilmark chocolates is a happy place. The world needs more Chilmark Chocolates.

Visiting A Friend

As an added spur of the moment treat, Lisa and I decided to stop in and see our friend, author Cynthia Riggs! We drove into the drive and we found Cynthia in her garden. With a hearty, “Hello!” and a beckoning wave, she motioned us over. As it turns out, Cynthia has been busy! She pointed out all of the vegetables that were doing well and the ones that were struggling a bit. Lisa and Cynthia debated over when they would be putting in their tomatoes. I think it was tomatoes. There was a lot going on, and I may be getting my wires crossed. Then we heard the bleating.

Goats in West Tisbury on a True Vineyard Day

Brownie and Flossie

Cynthia got goats! This was a new addition to her ever-growing menagerie. She took us over to see Brownie and Flossie. I loved them. I refused to go into the pen though because I saw them quickly try and eat Lisa! Well, her clothes anyway. It really is amazing how goats will eat anything they possibly can. I have felt that way myself, I must admit. It was terrific to see Cynthia. She has been one of my favourite people ever since we met two years ago on my birthday. Lisa and I drove to Oak Bluffs and went over our plans to spend time together on my return trip in June. Lisa is a true gem.

A beautiful home on a true vineyard day

One of the beautiful homes in Oak Bluffs

On a True Vineyard Day, I like to spend time in Oak Bluffs. Most of the things I enjoy doing in OB are outdoor activities. I walked Circuit Avenue and popped into Slip77  to say hello to my friends and check out the new clothes. As usual, their line is great this season. Make a point of going in and checking them out. Then I simply went for a walk. I actually had a purpose in mind when I started. I was seeking out my friend Doug’s place. He had given me the address and I was sure that I remembered it, but clearly I was mistaken.

Bus Stop on a True Vineyard Day

I wish all bus stops looked like this.

I wandered around the streets on the outskirts of Wesleyan Grove, and then eventually, through the campground itself. I took some photos—of course I did—and then made my way to The Inkwell. The more time getting sand in my flip-flops the better, right? I walked the beach and then sat in the sun and waited luxuriously for the bus. Those are words I never use when I talk about waiting for the bus in Toronto; however, sitting on a bench, facing the sun, with the waves rolling onto the beach behind me, is something that I call luxurious. And I gotta tell you, I don’t care how long the bus takes.

The Inkwell Beach

I like to get in as much beach sand as I can.

A True Vineyard Evening

I went back to 1720 House for cocktails and lively conversation. There were four of us with differing opinions. The art of conversation is a glorious talent. I love sitting down with someone who is not only willing to listen to someone with an opinion that is different from their own but eager to do so. I am one of those people. This was not always the case, but I am now. Listening to someone talk about their socio-political beliefs, and trying to see things from their perspective is excellent. I need to be able to ask questions and be receptive to that person’s questions about my perspective. Conversation is more about listening that talking. My mother taught me that. I had one of the best conversations that I have had in a very long time. Thank you Leonardo.

My original dinner plans were postponed until Sunday, so I headed back out into the night to find some food. I ended up taking the bus back to Oak Bluffs and having supper at Martha’s Vineyard Chowder Company. It was my first time there. I ordered the fish and chips because the gentleman beside me was eating it and it looked excellent! It was. I highly recommend it.

Owen Park Beach at night

Owen Park Beach at night.

After supper, I went for a walk along the fishing pier and the beach. The waves rolled in and I looked out over the water into the night. The black water and the night sky disappeared into a horizon that I could not see. The night was quiet. There was no one out on the beach but me. I thought about my Vineyard friends. The ones who were usually with me on nights like this. Eventually, I got back on the bus and headed back to Vineyard Haven, where I followed the beach back to the inn…more beach sand.

I crawled into bed and fell asleep very quickly. This True Vineyard Day had been a full rich day. I was awake long enough to realize that I got sand in the bed. I couldn’t have cared less. Hey, it’s The Vineyard.


  1. Sounds fabulous, I love living vicariously through your posts! I can’t wait to make it to the Vineyard sometime!

    1. I’m so glad that you are enjoying them! I can’t wait for you to have your first Vineyard experience.

  2. Hi! I love your stories!! It does sound like the perfect day!! I also ride the bus and feel the same way at the bus stops,where else can you wait in such a beautiful place?!

    1. Thank you so much! I’m so grateful that people are taking to them as positively as they are! I really appreciate you taking the time to provide feedback. I couldn’t agree more about the bus stops!! See you on the Vineyard!

  3. Loving your stories! I’m always anxiously awaiting my next trip to MV, even more now with all these new places to go!

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