Must Do’s Of Vineyard Haven

This past weekend, I stayed in Vineyard Haven. That’s a first for me. I have always stayed in Edgartown or Oak Bluffs in the past. Actually, if you want to get technical, I only stayed in Vineyard Haven when I was a little boy. My parents and I camped at the campground. I loved camping back then; however, as an adult, I like to have more than a sleeping bag to sleep on. I was eager to see what Vineyard Haven would have to offer me as it would now be my backyard. So, here is the third entry in my series of places and activities not to be missed when you visit Martha’s Vineyard! Hopefully, you have already read, ‘Must Do’s Of Edgartown‘, and ‘Must Do’s Of Oak Bluffs‘. Welcome to ‘Must Do’s Of Vineyard Haven’.

Eating Vineyard Haven

I don’t think that it will come to anyone’s surprise that of all of the Must Do’s of Vineyard Haven, eating is my favourite. Before I really spent much time in the town, that was all I really used it for other than getting on and off the ferry. The biggest reason for that is, of course, The Black Dog Tavern. The Black Dog Tavern was built in 1971, but it seems like it has been there for hundreds of years. It’s quite easy to suspend your disbelief. It’s easy to see it dating back to the years when Vineyard Haven was called Holmes Hole. The interior is beautifully aged wood decorated with artifacts from schooners and whaling ships long gone, and historic photos of the area.

Must Do's of Vineyard Haven Black dog

Black Dog Interior

Sitting at your simple wood table and bench, looking out over the harbour, it’s easy to feel like time has stood still. Some of my islander friends give me a good-natured ribbing, reminding me of what a tourist I can be sometimes, but I live in a concrete jungle most of the time. If I find peace eating an excellent breakfast, and drinking coffee, looking out on the beach, so be it.

Must Do's of Vineyard Haven Black Dog view

It’s hard to beat the view at The Black Dog

There are other terrific places to eat in Vineyard Haven. If you’re sticking with breakfast, The Art Cliff Diner is a great spot. I recommend going early. Actually, I recommend taking in all of my Must Do’s of Vineyard Haven early, especially during high season. I go for breakfast as soon as these spots open and I never have to wait for a table—even in August.

Must Do's of Vineyard Haven Art Cliff Diner

The Art Cliff Diner

I have only been out in vineyard Haven for supper once that I remember. A friend took me to La Soffitta. It was excellent! La Soffitta is an Italian restaurant on Main Street. We had a great time. If you’re there at the right time, the ladies at Grace Church of Martha’s Vineyard in Vineyard Haven are definitely in the running for “Best Lobster Roll on The Island”. There are a great many who swear by them. They are worth checking out.   There are still a few places that I really want to try in Vineyard Haven like Garde East and The Net Result on Beach Road—all in good time.

Shopping Vineyard Haven

When comparing it to it’s counterparts, Oak Bluffs and Edgartown, there are fewer shops in Vineyard Haven, but there are definitely some really cool ones. Just a couple of days ago, I was in one of my favourites, Le Roux at Home. Le Roux at Home is definitely one of my Must Do’s of Vineyard Haven. I still haven’t been all the way through it—it’s a lot larger than it seems.

Main Street Vineyard Haven

Main Street Vineyard Haven

The first time I visited Le Roux was with a friend who wanted to pick up an iron-mesh glove for shucking oysters. It’s exactly the same kind of glove Valerie Taylor had on her hand when she forcibly shoved her arm into a shark’s mouth to see if it would protect her. Imagine my relief to discover that my friend, Geoff, had discovered a far more reasonable use for his. Le Roux is full of other items of interest, should you not be planning on shucking oysters, shark wrestling, or charging with Richard The Lion Heart in the Crusades.

Le Roux is full of housewares and kitchenwares, both with and without a Martha’s Vineyard motif. When I was in there on Monday, I picked up some tea towels for my Mum. She loves tea towels and these had horseshoe crabs and sailboats in a very simple design. There are some great platters that I would happily bring home if I wasn’t so nervous about travelling with them.

Must Do's of Vineyard Haven Capawock Theater

Go see JAWS at Capawock Theater!

Whether you are looking for photographs, paintings, or sculpture, there are some excellent galleries in Vineyard. It’s also worth noting that The Capawock Theater is showing JAWS all summer long…just sayin’. Main Street Vineyard Haven is definitely worth the short walk from one end to the other.

Exploring Vineyard Haven

I checked off a big item on my Must Do’s of Vineyard Haven last weekend—I finally got to see the new Martha’s Vineyard Museum. They did a great job bringing the old building back to life. I would say “restoring” it, but that really doesn’t do their work justice. Restoration implies returning something to its former glory. This building has never looked this good in its one hundred and fifteen years of existence. The displays are marvellously curated. I have written about it extensively here. Take a moment and have a read, then please go and peruse the museum itself. You will not be disappointed.

The Fresnel Lens of The Gay Head Light at the MV Museum

The hike around West chop is a long one, but on a True Vineyard Day, it is a great walk. I love New England Architecture and there are some magnificent examples on this path, not to mention the West Chop Lighthouse. If it’s a hot day, bring some water, it’s a fairly long walk.

Owen Park, Vineyard Haven

Owen Park

Owen Park also holds a special place in my heart. Could it be because I once watched JAWS on its lawns? Or because its the place where I went out with my friends in the Catboat Association to marshal a catboat race? Maybe a little of column ‘A’ and a little of column ‘B’.  If you do decide to pick up a lobster roll at Grace Church, do yourself a favour and take it down to the beach in Owen Park. It’s a great little beach for kids to splash around in, or to simply read your book on a nice afternoon.

The Mansion House

There are a few places to stay in Vineyard Haven but the queen of them all is The Mansion House. Located on Main Street, The Mansion House has everything the seasoned traveller could hope for and at excellent prices. It has pet friendly rooms, rooms with soaking tubs, fireplaces, and balconies that overlook the harbour. You definitely couldn’t ask for a better location. Not only is The Mansion house within walking distance of the ferry terminal, it is steps away from all of Vineyard Haven’s shops, galleries, and restaurants including The Black Dog Tavern and Art Cliff Diner.

Mansion House of Martha's Vineyard

The Mansion House In winter

If you’re like me and you like to get in a good walk before breakfast, the walk from The Mansion House to the West Chop Lighthouse and back is one of my favourites. West Chop Light is a little off the beaten path which makes it a great way to start the day.

Vineyard Haven Martha's Vineyard

The view from The Mansion House roof top is spectacular!

It is also one of the few hotels on-island with its own gym, spa, and pool! If that’s not enough, the roof top patio is a great spot to relax with a complimentary lemonade and a good book, or simply watch the ferries and sailboats go by.

The Black Dog Tavern as seen from the harbour.

On this last trip, I spent more time in Vineyard Haven than I ever have before. I’m really glad that I did. I poked my head into stores and came across hidden finds that I hadn’t in the past. I walked along the beach a lot and got sand in my flip-flops. It didn’t matter whether it was raining or sunny. Hey, it’s the Vineyard!


  1. I sailed up to Vineyard Haven in 1985 and stayed at the dock at the BlAck Dog with my husband in our sailboat OZ. We stayed for a few days , fell in love with the place and by the end of the second day we had bought property. We now enjoy our house throughout the year coming often. I don’t need Prozac just look out of my window or go down to the lagoon and let the water deep into my thoughts and relax.

    1. I know exactly how you feel. I’m on the Vineyard several times a year. the island touches my soul like nothing else. I’m really glad you enjoyed the article. Thank you so much for your comments!

  2. After all these trips, Vineyard Haven is now where I always book to stay. Something about the pace or the location allows me to relax more than OB or Edgartown.

    A burger from the Waterside eaten in a chair on Owen Park watching the ferries come and go is the closest thing to paradise I’ve yet to manage.

    1. A burger from Waterside, eh? I’ll add that to my list! Thank you for your comment, Corey, and the great tip!

  3. The Net Result is hands down the best for seafood/takeout/sushi and food in general… def check it out! Also, State Road restaurant is a great place – but it’s in West Tisbury.

    1. I will check out The Net Result! Thank you for the suggestion! You are quite right, I forgot that State Road was that far out. I have made the appropriate adjustments—That’s the best thing about blogs! Bahahaha! I really appreciate your feedback. I hope you are enjoying the site!

    1. They’re definitely on my list of lobster rolls to try next trip! Thank you for your feedback!

  4. Thank you for these tips on VH, i always seem to go to Etown. I have eaten the lobster roll at The Net Result and Black Dog, but will definitely give your other recommendations a try. Found your site from Michael Blanchard’s FB page, so glad I did! I’m a Louisiana girl, with an MV Soul!

    1. Michael blanchard is such a great guy. I’m proud to count him among my friends. Let me know how you make out on your next MV trip! Thank you so much for leaving a comment. I really appreciate the feedback.

  5. Dropped off grandsons to do summer work on MV. Quickly decided they shouldn’t have all the fun so booked a house in Oak Bluffs. First time on MV and it did cast a spell. Going back to pick up the boys and now I have to stay in VH. Appreciate all your suggestions…it sounds wonderful. Was also very impressed with all the Covid careful measures taken and loved seeing all present in masks. Thanks again, Sandy

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