Martha’s Vineyard: What to do in Oak Bluffs

You know when you visit somewhere and it automatically feels like you belong? Of all the places I’ve been, I’ve only experienced it three times. Cuba, Paris, and now Martha’s Vineyard. After a couple of trips, I wanted to share what to do in Oak Bluffs!

My family and I had been wanting to visit Martha’s Vineyard for the longest time – especially knowing that one of its most popular places, Oak Bluffs, is full of Black history and where many Black people vacation. With COVID-19 in full swing last year, we decided that it seemed like a “safe” enough place in October and opted to make the 10+ hour drive. When we arrived, we instantly fell in love! We stayed in the most charming house in Oak Bluffs on the main street and were within walking distance of the downtown and ocean!

We ended up loving Martha’s Vineyard so much, that just two months later we booked another trip in January so that we could visit this past Memorial Day! When I say this place is amazing – I mean it. It’s charming, relaxing, unique, fun, casual, sophisticated… all of the things. Whatever your vibe, there’s something for you here. But, since there’s just so much to do and each town is unique – I wanted to split up my guides so that they’re not overwhelming. Let’s start with my favorite area: Oak Bluffs!

ARRIVING TO MARTHA’S VINEYARD

There’s two ferries that you can catch into Martha’s Vineyard. They both leave from Woods Hole and will take you into Vineyard Haven (another town we’ll cover) or Oak Bluffs. If you’re staying in Oak Bluffs, obviously that’s more convenient. However, our timing has never matched up, so both times we’ve taken the ferry into Vineyard Haven. The good news is that since it’s a small island, nothing is too far! You can easily hail a cab or an Uber. Or, you can opt for the #13 bus – which is what we’ve done. It comes every fifteen minutes and will drop you right in front of your door!

Another important tip is that if you’re driving, you can ride your car onto the ferry for an extra fee. I don’t think you need to bring a car, but I know some people prefer it. If you’re leaving your car, there’s two parking lots which are about 15-20 minutes away, so be sure to arrive earlier than needed. Each parking lot provides a shuttle to Woods Hole.

If traveling by ferry isn’t your thing, you can also fly into the Martha’s Vineyard Airport. My family and I are thinking of heading back next summer and we’re definitely flying. If you live closer, driving makes sense. However, our drive is just too long and exhausting – so flying it is!

The Steamship Authority has the full schedule.

WHERE TO STAY IN OAK BLUFFS

The last two times my family and I have used VRBO to book our house. We’ve booked the same house both times and we absolutely love it. It’s on the main road that leads into town and is easily accessible to other areas. I’d probably recommend staying in a house over a hotel – as you can stay in and cook on nights when you don’t want to go out and it’s just a much more comfortable lodging experience. However, if that’s not your thing – then you can certainly stay in a hotel!

Summercamp

Summercamp is located right in the heart of Oak Bluffs and we pass it every single day! It’s got an amazing location that’s right on the water and directly across one of the most popular restaurants, Nancy’s. The rooms are all very nice and lovely, and it’s actually situated right by the historical Gingerbread House Campsite (that I’ll dive into later). I’ve also heard great things from guests who have stayed there.

• Editor’s Note: There’s definitely more lodging options, but these I feel the most comfortable/knowledgeable about sharing.

WHERE TO EAT IN OAK BLUFFS

Where do I start?! There’s so many yummy places, so you won’t run out of places to try. I’d say that compared to somewhere like Edgartown, the food scene is a lot more casual here and not as formal or like fine-dining. You can certainly show up in jeans and you’ll be totally fine. Let’s dive in!

Nancy’s

Nancy’s is right in Oak Bluffs Harbor and has a gorgeous view of the water. It’s also multi-dimensional – meaning you can dine-in at the restaurant or order at their pick-up window. You can also just sit on their patio and have some drinks! My dad and I hung out on the patio and had some delicious palomas, and then another night our family ordered some delicious seafood and salads at the pick-up window! It’s one of the most popular spots in town, so you can definitely can’t go wrong.

Lookout Tavern

Lookout Tavern is probably one of my favorite restaurants in Oak Bluffs. It’s right up the street from Nancy’s and has another gorgeous view of the water and Ferry station. They have a cute little patio and the inside of the restaurant is totally wide open for fresh air and stunning views. I highly recommend the HOT lobster roll here. Of all that I’ve tried, I think this place has the best. Their cold lobster roll is delicious, but the hot one is where it’s at.

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Martha’s Vineyard Chowder Co.

This cute little restaurant is famous for? You guessed it! It’s clam chowder. Our last visit I literally ordered clam chowder wherever we went, and this one was delicious! Not too watery and not too creamy. But, if clam chowder isn’t your thing – they’ve got a really delicious menu! We tried the fish and chips, a yummy caesar salad, and a few other things. The service was also excellent and they luckily let us in during closing time!

Linda Jean’s/Sarah Brown’s

Initially these two restaurants were separate, but now they’re combined – with Linda Jean’s operating as breakfast during the day time and Sarah Brown’s operating at night for dinner. Both are incredible and I highly recommend you stop here. Linda Jean’s has such delicious – and affordable – breakfast, and Sarah Brown’s serves some of the yummiest soul food I’ve had! Think oxtails, fried chicken, and much more. It’s a nice switch up from all the seafood!

Back Door Donuts

Ugh, this place is amazing. I absolutely love donuts, so of course this is one of my favorite stops. It’s the cutest little shop right off of the main shopping road and has some excellent treats! The real fun, however, is the Back Door – which opens around 7pm each night for some fun specials. Their Maple Bacon donuts are the absolute best and we order a half dozen each time we go!

Mocha Motts

Can’t forget coffee! Mocha Motts has some of the best coffee I’ve ever had, and luckily they have multiple locations across the island. The Oak Bluffs shop is my favorite, and they give you a little card that wins you a free coffee after 12 stamps (and it’s nice that it counts per coffee and not per order if you have a group with you).

Offshore Ale Co.

I haven’t eaten dinner here, but I have stopped for drinks and chicken wings – and man is their patio super cute! If you’re looking for a quick pit stop, this is a great option. Just beware that like many places, it doesn’t typically open until 4pm.

WHAT TO DO IN OAK BLUFFS

Oak Bluffs is one of my favorite parts of the island, with Edgartown pretty much tied. As I mentioned, Oak Bluffs is pretty casual and laid back, so you can do a lot of leisurely strolling to take in the sites! When you’re not eating, these are some of the activities I recommend.

Tour the Gingerbread Cottages at Oak Bluffs Campground

This is one of my favorite things to do, and the last time we were there we visited twice! I believe there’s around 300 historical cottages on site and they’re all so unique and beautiful! Many were built in the 1800s and they’re so recognizable because of their bright and vibrant colors. While they’re fun and exciting to look at, there’s a lot of history behind them, too. It takes a bit of time to walk around the entire campground, but it’s totally worth it. In fact, you’ll see many of the owners sitting on their porches or tending to their gardens – and they’re all very friendly and nice to talk to!

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Stroll Down Circuit Avenue

Circuit Avenue is the main strip in Oak Bluffs and is full of fun little shops. If you’re looking for souvenirs for yourself or loved ones, this is definitely a good place to shop. Loads of unique sweatshirts and memorabilia to bring back for family and friends!

Visit the Beach

There’s several beaches to check out in Oak Bluffs, and the most popular is probably the Jaws Bridge where the movie was filmed! There’s State Beach, Eastville Beach, Jetty Beach, and several others – but my favorite is probably Oak Bluffs Town Beach which is located right by the ferry terminal. Depending on the time of the year, the traffic can vary – but the water is stunning and the beach has so many gorgeous shells! Luckily it’s right close to the downtown to grab a bite to eat if you get hungry. P.s. – there is a bit of seaweed.

Drive to Menemsha and Acquinnah Cliffs

Listen to me carefully. Drive – DO NOT TAKE A MOPED – to this part of the island. It’s on the west side of the island (so about 30-40ish minutes) and absolutely stunning! There’s different shops in Oak Bluffs that allow you to rent jeeps to get around, so it’s really easy. It’s totally different than Oak Bluffs and definitely worth the hike. Once there, definitely check out Larsen’s Fish Market or Menemsha Fish Market. You can purchase fresh fish to go or order some yummy seafood to eat on the dock. Whatever you do, don’t buy the steamed sole sandwich LOL.

After you’ve had your meal, head even further west to Acquinnah. Once at the top of the cliffs, you’ll take in the most stunning views. It’s truly breathtaking. You can also hike down to the beach if you want, but definitely be sure to check out the cute little vendors, too!

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• _{Editor’s Note: on our first trip to Martha’s Vineyard, we thought it would be super fun to take mopeds to this part of the island. Boy were we wrong. While it was super fun and hilarious – it was pretty nerve-wracking. We didn’t realize that you have to take the island’s highway (which is one-way on both sides) and it took an extremely long time. We also received a few honks and middle fingers because the mopeds were so slow! And on top of that, trying to hold your phone and scream directions on the back of a moped is incredibly difficult LOL!}

Check out the Harbor

The Harbor, which is right by Nancy’s, has beautiful views of the water and is usually loaded with beautiful boats. I’ve even been tempted to jump aboard some myself! It’s a beautiful boardwalk with lots of different restaurants to choose from, and is pretty relaxing to just take in the views.

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There ya go! My travel guide for What to do in Oak Bluffs. If you have any suggestions, I’d love to check them out 🙂