This past August I travelled to Martha’s Vineyard to attend the Beach Road Weekend music festival. It was the first international road trip with my campervan, Betty White, and the experience was everything I hoped for and more. In this guide you’ll find the best way to explore Martha’s Vineyard in 2 days, though if you have more time, I highly suggest sticking around for longer. The air is different here – clean, fresh, and rejuvenating. You’ll surely return home smiling.

Affectionately known by locals as MV, it is a popular spot for the rich and famous to enjoy their summers. The Obamas, Meg Ryan, Jennifer Lawrence, Michael J. Fox, and Spike Lee are just a few who frequently spend time there. Truth be told, this was about the extent of my knowledge of Martha’s Vineyard before travelling to the island. I thought I’d check out a few wineries and anticipated seeing a lot of people in overpriced preppy clothes.

Tir Na Nog Sailboat in Martha's Vineyard

Instead, I found quite the opposite.

It turns out Martha’s Vineyard is home to a grand total of zero wineries and there are even dry towns where no alcohol is sold! Talk about a slightly disappointing, though kind-of funny, misnomer. On the plus side, there wasn’t an upturned nose in sight. Everyone I met was down-to-earth, friendly, and laidback. I saw more straw hats, yellow hip waders, and colourful Wellies than popped collars. The festival had the most chill atmosphere of any I’ve attended, very similar to gathering at a friend’s (very large) BBQ. It was fantastic. In fact, each part of the island that I experienced had a similar vibe. It was another successful “bubble pop” of my preconceived notions.

On the second day, I was fortunate to meet a group of locals, including one I’ll dub the MV Mayor (he seemed to know every single person there!) and his Bostonian friend. They welcomed me in to join their crew, sharing island stories as we danced and sang the weekend away.

Gary Clark JR at Beach Road Weekend

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What is the Best Way to Explore Martha’s Vineyard in 2 Days?

To be fair, there are a million different ways that you could experience the island in 2 days. This itinerary is just one of many options. Depending on what you enjoy and how you want to spend your vacation, you may choose to take some parts of this plan and switch out others. At the end of the day, I hope that this blog post will give you a few new ideas, provide a framework for how to build your trip, and stoke your excitement for your upcoming travels!

Seagulls in the Sea on Martha's Vineyard

Where is Martha’s Vineyard Located?

Martha’s Vineyard is located on the eastern United States in Massachussetts. Nestled in between popular Nantucket island to the east and a series of smaller islands to the west. From Cape Code to Martha’s Vineyard it’s a short 45-minute ferry ride.

Plan Your Visit to Martha’s Vineyard

To best answer all of your questions about when’s the best time to visit Martha’s Vineyard, how to get to Martha’s Vineyard, and more, read this detailed blog post I wrote about everything you need to know to plan your visit to Martha’s Vineyard. It’s an excellent complement to this itinerary-focused blog post.

Travel with TMc at Moshup Beach

Day 1 – The “Little Bit of Everything” Day


You’ve got a busy day ahead of you, so don’t skip breakfast! As a night hawk, I will even go so far as to make the wild suggestion that you plan for an early start. Your first stop is a popular destination for both locals and visitors and no one likes a long lineup. Arrive at Black Dog Tavern in Vineyard Haven no later than 8:30 am and, fingers crossed, that should do the trick. It will be worth it to enjoy your breakfast or morning cup of Joe while overlooking the Vineyard Haven Harbor.

ACTIVITY (History & Sight-Seeing)

Next, it’s time for some fresh air and unique sight-seeing as you head over to the Gingerbread Cottages in nearby Oak Bluffs. Don’t be fooled by its official name. The Martha’s Vineyard Camp Meeting Association is no longer a campground, though that’s where it got its start in the mid-1800s as a Methodist campground. Today there are 330 storybook homes you can walk or drive by and a Cottage Museum where you can book tours to learn more.

Another nearby morning itinerary stop is the historic Flying Horses Carousel. It opened in 1884 and is the oldest continuously running platform carousel in the USA. Check out this blog post I wrote on everything you need to plan your visit to Martha’s Vineyard to learn 2 more fun facts about this local landmark.


It’ll be time for lunch before you know it once you’ve worked up an appetite on the Carousel and while on your tour of the Gingerbread Cottages. For a sit-down meal outside, head to Waterside Market. They’re open from 7am until 5pm every day and have got a great selection of all-day breakfast and lunch options. Whether you choose the famous Tex Mex breakfast seen on Diners, Drive-Ins, and Dives or one of their flavourful sandwiches or salads, your tastebuds will be satisfied. You’ll also find an intriguing selection of local bevvies, both alcoholic and non-alcoholic.

Waterside Market in Vineyard Haven

If you’re looking for just a wee midday bite, Little House Cafe has something delicious for every meal of the day, plus baked goods, takeout options, and more.

Last, we can’t forget dessert. There are plenty of ice cream options in Oak Bluffs to choose from. Mad Martha’s Homemade Ice Cream has dairy and non-dairy options, with local flavours like Apple Fritter, made with fritters from Back Door Donuts, Chilmark Coffee, in collaboration with Chilmark Coffee Company, and MV Sea Salt Caramel, made with salt from Martha’s Vineyard Sea Salt. Personally, I’ve got my eye on Sinful Chocolate, Lotsa Dough, and Snickers. Another local ice cream shop named Carousel Ice Cream Factory has a neat eclectic old-timey feel.

ACTIVITY (Beach & Shopping)

Time for the beach! There are 3 options within close range of each other: Oak Bluffs Town Beach has an accessible entrance and shallow water, the mostly sandy and a little rocky Eastville Beach is the perfect spot to watch the drawbridge allow through passing sailboats, and the sandy shallow Joseph Sylvia State Beach where the classic movie Jaws was filmed. Don’t forget to snap a photo on the Jaws Bridge!

Dead Crab on Beach

If the beach isn’t your cup of tea but you love a shopping spree, there are 2 areas I’d suggest you put on the list. In Oak Bluffs there’s tons to choose from along Circuit Avenue. In Vineyard Haven, head to Main Street for plenty more options. Between these 2 streets you’ll find several local stores selling clothing, art, and unique items to decorate your home or bring home as gifts.


It is fair to assume you’ll have worked up quite the appetite after a full day of activities. Thankfully, there are a plethora of dining options to suit a variety of dietary needs and cuisine preferences. Midnight Taco dubs itself “Coastal-Inspired Mexican food”. They serve tacos, burritos, bowls, birria, and local ceviche. The Seafood Shanty has been satisfying customers’ cravings for fresh seafood for over 60 years. They’ve got everything from seaweed salad and sushi rolls to a grilled swordfish salad, New England clam chowder, and oysters galore. We headed to Lookout Tavern to try their award-winning lobster roll, voted the best on the island since 2012, and WOW was it delicious! Highly recommend. Be prepared for a lineup as it’s first come first serve…but totally worth it. If you’re looking for somewhere a little funky or even a late night eats spot, Mikado brings theatrics to their sushi platters.

ACTIVITY (Live Music, Bar Scene, Midnight Snacks)

If you’re into after dinner activities, there are quite a few available to you on Martha’s Vineyard. Start with a live music gig at The Loft before heading out to The Ritz for a night of dancing (and possibly even more live music). I couldn’t find much in terms of updated websites or social media for The Loft, but having been there for a gig I can definitely pass on the recommendation. If you scroll to the bottom of the link I shared for it above where it says Events, that seems to have the most up-to-date information.

The Ritz is a local dive bar that was also a location for the reality TV show Summer House: Martha’s Vineyard. I seem to have good timing when it comes to stumbling upon film and TV sets, which is exactly what happened walking outside the bar on the 2nd night I was on the island. Bringing good vibes to the scene since 1944, the historic bar and music venue is an awesome spot for a night out (which is where I ended up on the 3rd night). I don’t know if I lucked out with the band, an enthusiastic crowd, and an overall great atmosphere or if it’s always like that, but I’d definitely say to check it out if you’re looking to dance the night away.

To top off your day, why not induce yourself into a sugar coma before bed? BackDoor Donuts serves fresh gourmet donuts until midnight. Enough said.

Day 2 – Beach Day in Aquinnah


As much as I can, I make it a point on the blog to only suggest places I’ve been to or experiences I’ve personally had. Once in a while, however, I find out about a cool spot after I’ve left a destination or sometimes I just can’t fit everything I want to in one trip. This next recommendation falls into that category. Despite not having dined here, Behind the Bookstore is highlighted and circled on my list for next visit as a fabulous, quirky, and tasty spot to check out. Food service begins at 8am in the space behind Edgartown Books. If that doesn’t sound like the perfect romantic way to greet the day, I don’t know what is. If you’re a coffee-only breakfast person, you can get your java hit as early as 7am. As a Canadian, their breakfast prices aren’t for the faint of heart (roughly $30)…but what’s life without a splurge here and there, right? Go, send me pictures, and help me live vicariously through you.

ACTIVITY (Culture)

The Aquinnah Cultural Center is easily in one of the top 3 places to visit when on Martha’s Vineyard. Here, the Aquinnah Wampanoag people preserve and share their history and present-day culture with visitors to the island. They offer educational programming and exhibits that provide insight into their 12,000 year history on the land and their enthusiasm for their traditions. The building is even a living testament to their presence, since it was the ancestral home of the current director! Stop by one of the many nearby artisan businesses on your stop home to find a special memento of your travels.

Long Grass Coastal Views in Aquinnah


Day 1 had a packed itinerary, so slow things down today with a picnic at Moshup Beach. Stock up on sweet and savoury local favourites from the historic Chilmark General Store or head to the Stop and Shop for groceries. Please make sure to leave no trace and pack up everything before you leave the beach. It is a very special place and, as always, it’s important to take care of the environments we pass through.

Man Strolling in Aquinnah


In line with the relaxing vibe for day 2 of your Martha’s Vineyard itinerary, open a book (possibly one you purchased from Edgartown Books!), go for an ocean dip, or take a walk along Moshup Beach after you’ve finished lunch. Make note that there is a section of the beach that’s nudist-friendly. Moshup Beach is a fascinating place to explore, especially at the far end of the beach where you’ll discover the mesmerizing Gay Head Cliffs. The vibrant clay cliffs are a national landmark, protected and cared for by the Aquinnah Wampanoag people. Rumour has it that from time to time the cliffs reveal fossil bones of whales, camels, and wild horses. I didn’t see any when I visited, though there was plenty of marine and bird wildlife. It is forbidden to remove any pieces of clay due to erosion so please keep that in mind.

Also known as the Aquinnah Cliffs, the 2 best suggestions I would give to you are to go during the week to avoid summer crowds, and to use the washroom by the parking lot or at a local store before heading down to the beach. It’s roughly a 10 minute walk from the parking lot, or closer to 30 if you like to dawdle like me. Beware of the poison ivy that lines the path to reach the beach!

Stunning Colourful Cliffs on Martha's Vineyard


The best way to explore Martha’s Vineyard in 2 days is to warp things up in an epic way. If you’re staying on Martha’s Vineyard for 2 nights, do not miss the sunset at Menemsha Beach. It’s said to be the best spot on the island and the parking lot fills up quickly, so arrive a few hours before the sun disappears. Perhaps you’ll wish to enjoy the rest of your picnic from here or maybe you’ll eat at a restaurant after the sun has gone down. There are plenty of dining options I’ve outlined for you in the downloadable map below. Let’s call this the “choose-your-own-adventure” portion of the itinerary.

Frequently Asked Questions About Martha’s Vineyard

How Big is Martha’s Vineyard?

Martha’s Vineyard is deceptively big! If traffic isn’t an issue, it takes about 45-60 minutes to travel from end to end by car. Triangular in shape, the widest distance is approximately 42 km and the longest distance running north and south is about 13 km. Many people bike around the island, and you can too, just budget more time in your day for getting from place to place, especially since you wo’nt find bike lane anywhere.

How Much Does the Ferry to Martha’s Vineyard Cost?

It depends. I know, that’s exactly the answer you were looking for… The ferry to Martha’s Vineyard costs anywhere from free (children under 4) to USD $135 one way for vehicles between 17 and 20 feet long in peak season. For a more detailed response, check out this post here.

Is There Public Transportation on Martha’s Vineyard?

Yes, there are options for variou public transportation services on the island. The Vineyard Transit Authority (VTA) connects the 6 towns and all buses are accessible for those with a handicap. You can pay-as-you-go, or buy 1-day, 3-day, or 1-week bus passes in-person on the bus or at the Steamship Authority.

There are also many taxi and private car companies in Martha’s Vineyard.

Is it Expensive to Travel on Martha’s Vineyard?

Between the MV Family Campground and a HI-Hostel, the efficient public transportation system, and the numerous free outdoor activities that are available, your trip to Martha’s Vineyard can be as budget-friendly or as bougie as you want it to be!

Travel with TMc pitched a tent at MV Campground

How Many People Reside on Martha’s Vineyard Year-Round?

The population of Martha’s Vineyard fluctuates wildly from season to season. Year-round, roughly 23,000 permanent residents call this piece of paradise home. Summertime is another situation entirely, when nearly 200,000 people inhabit the island.

What’s the Best Length of Time to Visit Martha’s Vineyard?

The answer to this question, like many in the travel sphere, is completely subjective. You can definitely make a day-trip out of your time there if you’re already on the east coast. Just as easily, you could spend a weekend, week, or a whole summer! Whatever you choose, hopefully your first time won’t be your last time on Martha’s Vineyard.

Does It Make Sense to Visit Martha’s Vineyard for Only 1 Day?

As previously mentioned, if you’re already in Cape Cod you can definitely spend a day at the beach, restaurant hopping, or frequenting the many different museums. A little bit of time is better than no time at all!

What Makes Martha’s Vineyard So Special?

There are a plethora of reasons that Martha’s Vineyard is a special place. In no particular order, here are a few of them.

  • The landscapes are stunning, wherever you are on the island. Don’t miss Gay Head Cliffs. That one’s top shelf.
  • There’s a thriving artistic community across several disciplines, from dance to pottery to Indigenous art to painting to jewelry and more.
  • Small business reigns here. There are a grand total of zero chain stores. Hallelujah!
  • Martha’s Vineyard has been a haven for vacationing Black communities for over century, as well as a symbol of Black prosperity. For some context, Massachusetts was one of the first states to abolish slavery and Martha’s Vineyard was a part of the Underground Railroad. There is an established history of safety, possibility, and freedom.
  • Another minority group, the Indigenous population, also have a respected place in society on Martha’s Vineyard. The MV Mayor I mentioned above remarked in surprise that a land acknowledgement at the festival was given by someone who wasn’t Wampanoag. In my ignorance, thinking a land acknowledgement was a land acknowledgement and not yet knowing who the Wampanoag were, I asked him why. He told me about them, that their history is an important part of the island’s school curriculum, and how integrated the island’s various communities are. I was pleasantly surprised yet again and tucked this new information away to learn more about after the trip.
  • Quality food is a part of everyday life. Thanks to dozens of local farms, active fishing communities, and several farmers markets, eating farm (or ocean) to table is integral to the island’s cuisine.
  • Some might even say Martha’s Vineyard is a perfect romantic destination. With many vantage points from which to cozy up while watching breathtaking sunsets, or tree-lined roads down which you can enjoy leisurely bike rides, or music festivals at which you might experience a meet cute, the potential is definitely there. Then again, if you’re open to it, romance can happen just about anywhere!

Where Did the Name “Martha’s Vineyard” Come From If There Are No Wineries?

I was gobsmacked to learn that Martha’s Vineyard didn’t have a single winery. Who had the brilliant idea to name it that then and why?! It turns out, there are wild grapes on the island, but they stay on the vine. In fact, many of the islands communities have been or still are dry. As in, they don’t sell alcohol. Are you as confused as I was when I first learned these facts?

As for the inspiration for the island’s appellation, there was an English explorer named Bartholomew Gosnold whose daughter (or mother-in-law…the jury’s out on this) was called Martha. As the Brits put it, he discovered the island while sailing around with the first recorded European quest to Cape Cod in 1602. Be first or be best to leave your mark, right? He also gave Cape Cod its name. Of the several articles, blogs, and tourism websites I read, one suggested that Gosnold had 3 daughters: Nancy, Elizabeth, and Martha. Geography buffs’ ears might already be perking up after reading that little tidbit. According to GoMartha’, he named the string of islands between the mainland and MV after Elizabeth, the island of vines after his daughter Martha, and the Nan “took” the farthest island. There is nothing to suggest that this is the correct story, but I like it so I’m sharing it!

Being the history amateur that I am, I’d be remiss not to share that Martha’s Vineyard is of course not the original name for the island. The Wampanoag tribe refer to it as Noepe, meaning the “land between the streams”.

Souvenir Boat in Vineyard Haven

Get a Sneak Peek of Your Martha’s Vineyard Trip!

Curious to get a sneak peek of these destinations and suggestions before you go? Watch my New England Instagram story highlights from my trip to Martha’s Vineyard. Still have questions about the island or travelling there? Send me a DM on Instagram and I’ll be happy to help where I can.

Sneak Peak of Martha's Vineyard

BONUS Downloadable Map for Your Trip!

About TMc


Me having a seat in front of one of the famous Brighton Bathing Boxes in Australia!

Heya! I’m Tara (Tar-ah)! Welcome to Travel with TMc where you’ll find quirky language tidbits, travel hacks for Canadians, and stories from the road. I hope you enjoy!
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