Must Do’s Of Oak Bluffs

First of all, thank you to everyone who read and enjoyed the first post in this series Must Do’s Of Edgartown. I’m really grateful for everyone who has been following along as I try and fill my website with entertaining and informative content regarding our favourite island. It only seemed logical that the next instalment be the Must Do’s Of Oak Bluffs. Oak Bluffs and Edgartown make up what is called “down-island”. Depending on who you talk to, Vineyard Haven is also down-island (can you guess where my must-do series will be going next?), but that seems to be a matter of debate. A debate that I really have no say in as I am not only not an islander, but I’m a Canadian to boot!

What I can tell you is that ‘up and down island’ is a nautical reference to the distance from the Prime Meridian. The Prime Meridian is the longitudinal equivalent of The Equator. It is sometimes referred to as “The Greenwich Meridian” because it passes through Greenwich, England. Greenwich is 0º longitude. As we move farther east or west from that line, the degrees in longitude increase; therefore, the west half of the island is higher up on the longitude scale than the east side. Anyway, back to Oak Bluffs…

Eating Oak Bluffs

When it comes to culinary Must Do’s of Oak Bluffs, it’s hard to know where to begin! There is a lot from which to choose! I’m starting with coffee. My go-to in Oak Bluffs for coffee has to be Mocha Mott’s. There are several flavours if that’s your thing but I tend to be a classic kinda guy. I like my coffee strong and simple. I’m also good for a latté now and again. I really like the strong coffee at Mocha Mott’s and the lattés are great! I also like the fact that they open early. That’s a real deal breaker for me. If you have read any of my other posts, you’ll know that I’m an early riser. I like to get up and at ’em. Being able to get a coffee nice and early is a good thing.

Mocha Mott's—Must Do's of Oak Bluffs

Mocha Mott’s Good Coffee… it is too!

Breakfast is a treat in Oak Bluffs and there are a few places that I have yet to try. Linda Jean’s on Circuit Avenue is always busy mid-morning. Line-ups out the door. That’s the other great thing about being an early riser—I never have to wait for a table ever, even in August. Martha’s Vineyard Gourmet Café & Bakery makes amazing baked goods, pastries, and they serve great coffee! They also make the best apple fritters that I’ve ever had in my life. No joke.

Circuit Avenue Oak Bluffs

Circuit Avenue, Oak Bluffs

If you read my Martha’s Vineyard Mysteries, you’ll know that my characters are always eating apple fritters. Although, through an error of memory, I credited the fritters to another place entirely. It is these fritters that I remembered so fondly. By the time I realized my mistake, it was too late. I was three novels in. This is the home of Back Door Donuts! Line up speakeasy style in the evening for a donut fresh out of the deep fryer. You’ll think you’ve died and gone to heaven. Then again, you’ve thought that since you got on-island anyway, haven’t you?

I have also already written extensively about the lobster roll at The Lookout Tavern. It is my favourite on the island. The Lookout is also known for its sushi. so, if you’re a sushi person, this is a great spot to sit and look out over the ocean with a pint or—even better, a real Canadian treat—a Bloody Caesar!! Bloody Caesars blow Bloody Mary’s out of the water! You have no idea how excited I was to discover that the restaurant that makes my favourite lobster roll also makes Bloody Caesars. Thank you!

Nancy's Restaurant Oak Bluffs

Chilling at the rail on Nancy’s upper deck

Nancy’s Restaurant is an amazing place to sit on the upper deck and watch the world go by. My friends and I have spent many an hour on that deck and even made some very good friends doing it. The staff is amazing and always seems to be having a fantastic time. I think it’s impossible to be in a bad mood at Nancy’s. I’m also a big fan of The Sand Bar which is right next door. Coop deVille is a little farther down the line, but I haven’t been there yet! It’s definitely on may list as I have heard nothing but great things.

Nancy’s, Sand Bar, Coop DeVille, are all on this strip.

There are almost too many great spots to mention! The Red Cat Kitchen on Kennebec is one of my favourites. So is Off Shore Ale, right up the street. I’ve heard great things about Fat Ronnie’s but I haven’t been yet. It’s on my list. Giordano’s is my favourite sit down pizza place, but there are a lot of places that I haven’t tried yet too. The list is endless. Are you looking for an evening of live music? The Ritz is your place. My friends, Ryan, Kurt and I went there last year after The Best of The Vineyard and we had a blast!

Shopping Oak Bluffs

There are shops for just about everything you could want in Oak Bluffs. This should close as no surprise, because Oak Bluffs was the only town on Martha’s Vineyard that was actually designed with tourism in mind. The rest of the island either was either developed for whaling or farming. Oak Bluffs was originally part of Edgartown, but when it broke off it was developed for the growing tourist trade that was coming in from America.

Must Do's of Oak Bluffs

Slip77 are so hip, it hurts.

Most, if not all of my novels mention a store on Circuit Avenue called Slip77. There’s a good reason for that—I love it. Slip77 has a great vibe, a very island vibe. They play cool music and have terrific staff. The owner, Christina Izzo, puts a lot of effort into selecting her merchandise each season and it shows. Slip77 has clothing and accessories with a vacation feel but a lot of their options are geared toward people who don’t want to feel like their wearing billboards. They’re subtle, classic, cool. Check them out.

h. falk designs

h. falk designs do amazing work

Driftwood Jewelry is a beautiful little spot and I love the fact that they are always willing to have pop-ups showcasing local artists. One of my particular favourite local jewelry designers is h. falk designs. h. falk designs’ work is fresh and exciting even though the stones and metal give the pieces familiarity and warmth. That kind of classic modernity is difficult to imbue. Her work reflects the island itself.

South Beach Outfitters Oak Bluffs

South Beach Appliances has something I really dig…

There’s a Vineyard Vines in Oak Bluffs too. There’s one in Edgartown, Vineyard Haven and Oak Bluffs. They got their start here and they put a great energy into the world. I love their positive attitude. South Beach Appliances is a great spot to pick up souvenir-type shirts, etc. I guarantee you that every JAWS fan has, at the very least, stopped in to see what they have.

Exploring Oak Bluffs

Many of the Must Do’s of Oak Bluffs that are my absolute favourites are things that are out and about! The Flying Horses Carousel is so much fun. It is the oldest functioning platform carousel in North America. Have you tried to grab the brass ring yet? Give it a shot. My favourite beach for just chilling is in Oak Bluffs. Inkwell Beach is a great place to just walk over and have a relaxing swim. Just the a break from life’s goings on and relax. The water isn’t very deep. It’s warm and calm. You couldn’t ask for a better family beach.

Inkwell Beach. Relax.

Of course there is the Methodist Campground, Wesleyan Grove, or as most people call it—the gingerbread cottages. I’ve never experienced anything like it. Take a walk though the multicoloured cottages and their meticulously tended gardens. The tabernacle is in the centre of it all and in the summer there are usually events taking place whether its a wedding or a concert or a graduation. I wrote a more in depth article about the campground and it’s worth checking out. It has a pretty cool past.

The cottages of Wesleyan Grove

So, there you have it. From doughnuts to methodists, Oak Bluffs has a lot to offer anyone who is looking to explore. Maybe you just want to sit with a Mocha Mott’s Coffee in the park and watch the ferries come in and go out. You can do that if you want to—hey, it’s the Vineyard!



  1. Take an easy stroll to the other side of the harbor and visit Enchanted Chocolates. We feature 72% cacao fine chocolates. We actually make our own confection bases- not bought from a factory or out of a tub. Almond Butter Crunch and Sea Salt Caramels are year round favorites. And there are always chocolate samples 😋

    1. I will come and see you for sure on my next trip. It will give me something new to write about! Thank you for the suggestion!

  2. We are coming to Oak Bluffs via a cruise ship in May. Is there any place to rent bikes? We love all of your suggestions but would love to rent bikes as well.

    1. There are lots of bike rentals all over the island. You will see them as soon as you disembark. Enjoy!

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