What to Do in Martha’s Vineyard For a Day (or Two!)

You’ve searched for the perfect destination for a day trip or weekend getaway in New England, and landed on the coastal island of Martha’s Vineyard, Massachusetts. Great choice! Now, we’ll help you nail down the important details, including how to get there, getting around, and what to do in Martha’s Vineyard for a day or two. Read on to discover your best options while experiencing this Cape Cod gem.

Vineyard Haven, Martha’s Vineyard
(Photo: Jon Burke)

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Planning Your Day Trip to Martha’s Vineyard

CONTENTS: In this article, you will learn everything you need to know about the best way to spend the weekend on Martha’s Vineyard, including:

Where is Martha’s Vineyard?

A small island considered part of Cape Cod, you’ll find Martha’s Vineyard located seven miles off the coast of Massachusetts.

The northern point of the island is south of Falmouth. It’s southeast of the Elizabethan islands and separated from the Massachusetts mainland by Vineyard Sound.

Martha’s Vineyard is 29 miles west of Nantucket Island.

Where is Martha's Vineyard - Google Map
(image: Google Maps)

When to Visit Martha’s Vineyard

Like most of New England, you’ll find the weather for Martha’s Vineyard is warmest in the summer months and very cold during winter. While mostly sunny and in the high 70s F during July and august, Martha’s Vineyard weather has it’s damp and foggy moments as any island would. In the winter, temperatures plummet well below 0-degrees F.

The most preferred seasons by couples are right before the shoulder seasons (right before and after a summer break for schools), September is traditionally the wedding season and most stores begin their end of summer sales. 

Now that you know the best ways to get to Martha’s Vineyard, when to visit, and how to get around, let’s get into the weekend itinerary for what’s affectionately known as ‘the Vinyard.’

How Do You Get to Martha’s Vineyard?

You can get to Martha’s Vineyard several ways: 

  • By one of the Martha’s Vineyard Ferries from Falmouth, Hyannis, or New Bedford MA, and N. Kingstown RI 
  • From Nantucket to Martha’s Vineyard by the inter-island ferry
  • By Plane into the Martha’s Vineyard Airport via Cape Air
  • On a private boat to Martha’s Vineyard

Most people take the Martha’s Vineyard ferry from Wood’s Hole in Falmouth. It’s also the most cost-effective option.

You can easily plan a day trip to Martha’s Vineyard, but we recommend spending two days, if you can.

The Ferry Schedule to Martha’s Vineyard from Woods Hole 

If you are traveling between Vineyard Haven and Oak Bluffs you need to be aware of the Island Queen fares and ferry schedule. This is especially true if you are traveling to Vineyard Haven from Oak Bluffs, as oncoming boat of cars can create a traffic jam that takes a 10 minute drive and turns it into an hour drive due to the congestion in the center of Vineyard Haven. 

The best ferry to Martha’s Vineyard from the Mainland is from Woods Hole in Falmouth, MA. If you’ve got some extra time, you might even plan to stay over in Falmouth before heading to the island. 

If you do, be sure to get an early start so you can maximize your time on the Vineyard. The ferry ride takes about 45 minutes, depending on weather, and you’ll want to arrive at the gate at least an hour in advance.

For an additional fee, you can bring your car over on the ferry. Be sure to check the Martha’s Vineyard ferry schedule and make reservations if this is your plan because the cargo space fills up quickly, especially during summer months.

South Beach in Edgartown, Martha’s Vineyard
(Photo: Jon Burke)

The Three Main Towns of Martha’s Vineyard 

Like most of Cape Cod, Martha’s Vineyard is divided into towns and villages. There are several towns on the island but the three main ones you should know are: Vineyard Haven, Oak Bluffs, and Edgartown These three Martha’s Vineyard towns can be thought of as the working town, party town, and posh town, respectively.

  • Vineyard Haven is a “dry” town, meaning no alcohol. It’s quiet and the main street has a handful of small shops and galleries. 

    If you happen to be staying in the area, you can spend about an hour walking around before running out of things to do. 
  • Oak Bluffs is the party town of the island. It hosts several bars, popular restaurants, an arcade for the kids, and the oldest operating platform carousel Flying Horses.

    Most tourists and day trippers flock to Oak Bluffs for it has something for everyone, beaches, parks, souvenir stores and plenty of ice cream parlors to pick from. 
  • Edgartown is the posh, fancy, everything looks pristine town. Imagine how you picture Vineyard Vines, because it is home to the original.

    Edgartown hosts the fancier clothing stores and a handful of restaurants. Yet due to how small the streets are it can feel impossible to drive through it during the summer season. 

Martha’s Vineyard is larger than most tourists think. This ends up drastically affecting their plans. 

To be prepared, the island is 87 square miles and consists of several large towns and counties. To give you an idea if you are from the Boston area, the length of the island is similar to the distance from Framingham to Boston, taking between 45 minutes to an hour to drive end to end. 

Best Ways to Get Around the Island

Once you get to Martha’s Vineyard you’ll want to have a way of getting around so you can fully explore the island on your Martha’s Vineyard vacation. 

Do I Need A Car on Martha’s Vineyard?

If you plan on spending more than a few hours on the island, you’ll want to have your own car or rent one car while you’re visiting Martha’s Vineyard.

To bring your own vehicle, there’s the car ferry to Martha’s Vineyard.

Or you can rent a car on Martha’s Vineyard. The most common rental car on the island is a four door jeep wrangler, which is especially fun if you want to drive on the beach.

There are two over-the-sand vehicle beaches on Martha’s Vineyard: 

  • Norton Point – You can get a Day Pass here
  • Cape Poge &Wasque – You’ll need to invest in an annual pass, here

That said, If you plan on having a car I strongly suggest not staying in Edgartown unless you have guaranteed parking. During the busy season even the locals that live in Edgartown struggle to find parking due to the narrow streets and overflow of people. 

Should I Rent a Moped on Martha’s Vineyard?

You can rent a moped on Martha’s Vineyard, but I don’t recommend it. 

Here’s why.

  1. Mopeds are very dangerous and cannot go the speed limit on the main roads. 
  2. You won’t be able to transport all of your things and impatient drivers will try to pass you.

In fact, mopeds have been banned in Edgardtown and there is a movement to ban mopeds on Martha’s Vinyard.

Can I Rent a Bicycle on Martha’s Vineyard?

For exploring the local area, you’ll find it easy and fun to rent bicycles. There are lots of paved paths and lovely (but hilly) country roads perfect for biking in Martha’s Vineyard. 

You’ll find bike rental shops in the main towns, but if you’re in Edgartown, one place is R. W. Cutler Edgartown Bike Rentals.

Ride the Martha’s Vineyard Bus 

There are public busses that go between the main towns on the island but you are then putting your schedule in the hands of someone else. 

You can also opt for Uber or a Martha’s Vineyard Taxi.

2 Day Trip to Martha’s Vineyard Itinerary

Scarred Cliffs at Gay Head in Aquinnah, Martha’s Vineyard
(Photo: Jon Burke)

Whether you’re spending one day in Martha’s Vineyard or more, you’ll find the trick is to enjoy the highlights of the Vineyard while beating the crowds, but be aware you cannot escape them during the peak of the busy season. 

With some modification, you can easily convert this weekend getaway to a day trip to Martha’s Vineyard. 

Things to Do on Martha’s Vineyard – Day 1 

The first day starts early. 

Breakfast at The Black Dog or Art Cliff Diner

If you love thick, fluffy, plate sized pancakes then the morning starts by having breakfast at the Black Dog Tavern in Vineyard Haven. The interior of the restaurant presents an atmosphere of being inside an old pirate ship with wooden seating while looking out onto the Vineyard Haven harbor. 

You should try to be there by 8:30am at the latest, because the wait can stretch to over an hour if you get there too late. 

Another popular breakfast diner in Vineyard Haven is the ArtCliff diner, beloved by tourists and locals for homemade jams and marmalades, it can be even harder to find a seat here than at the Black Dog due to its limited seating capacity. 

Prepare for A Day at Martha’s Vineyard Beaches

Once you’ve satisfied your hunger, or you’re just rolling out of bed if you skipped breakfast, you want to pack up your car for a day at the beach. 

Here is the beach gear you might like to pack: 

  • Beach Chairs
  • Beach Towels
  • Balls, toys, a book, headphones, a boogie board, or whatever you enjoy at the beach
  • A cooler with snacks and water
  • Sun protection, whether that means sunscreen and sunglasses, an umbrella, or UV protective clothing

If you happen to stay near one of the grocery stores, I would suggest buying some snacks to eat throughout the day. Make sure you keep everything closed though. The seagulls can be tenacious.

Drive to South Beach

Once everyone is in the car, make the drive towards South Beach. This long beach stretches across the bottom of the island. 

Make sure to stop at Morning Glory along the way, especially if you missed breakfast. Morning Glory is a farm stand that makes warm pastries daily, provides fresh produce, and you can get a great cup of coffee or smoothie. This is a great time to pick up some healthy snacks to keep you energized. 

Related Article: Discover more easy ways you can combine travel and fitness, click here.

Growing up my father would make sure we all got to the beach around 10am so that he could set up in his favorite spot on the far right side of the beach, but now more than ever you want to get to the beach early on Martha’s Vineyard. 

Over the years hurricanes have dramatically affected the beach, and it is about a quarter the size it used to be because of the loss of sand. What used to feel like a football field wide is now about 15 yards. 

The primary draw to South Beach has always been the waves. Though they vary on the weather and season, at times the waves can build up to be huge swells. They can range from small waves that roll up to your knees or tower over your head that you can body surf all the way to shore. 

Relocate to State Beach

I recommend staying at South Beach for 3-4 hours before packing everything up and moving to State Beach

Home to “Jaws Bridge”, State Beach is always packed with tourists gathered to jump off the bridge into the canal. 

The jump in retrospect is not very high but only appears high as you stand atop the railing next to the “Do Not Jump” sign, but this is a jump that kids make all the time, you’ll be fine as long as you can confidently swim in a current. 

Sunset in Menemsha

After spending 1-2 hours testing your daredevil self, I recommend returning to your hotel to shower off all the salt water and freshen up. But don’t get too comfortable for there is one last beach activity left on the day. 

If you haven’t already, go to the store and buy your favorite beverage and appetizers for happy hour with a sunset. You’ll then make the drive to the small harbor town of Menemsha to enjoy the best sunset spot on the island. 

Get there a few hours before sunset – the parking lot fills up fast.

On a clear night, the sun will slowly dip below the horizon as its gaze warms the body as it descends. 

Spend the Night on the Town in Oak Bluffs

Once the sun sets, return to Oak Bluffs to spend the evening enjoying the town. 

Depending on what you enjoy, you may find yourself:

  • hunting down the perfect ice cream spot
  • picking which waterside bar you want to sit by
  • button mashing at the local arcade. 

The sweet tooths of your group will clamor to know what a line is doing in the back of a grocery store. 

What you will find out is starting in the evening the bakery in Oak Bluffs starts its tradition of backdoor donuts. They serve freshly made gourmet donuts out their backdoor until midnight. At peak hours (after families have had dinner) the wait can reach up to two hours long, but it’s worth it. I’ve traveled all over and still have not found a donut I enjoy more. 

Alternative: Dinner Cruise on the Alabama, Johhny Hoy.

If you’re staying over, consider these places:

Things to Do on Martha’s Vineyard – Day 2

Edgartown Lighthouse, Martha’s Vineyard
(Photo: Jon Burke)

Explore the Island on Foot

The following morning can be a slower one, unless you missed out on a good breakfast spot the previous morning. A mellow start can lead into exploring the area around where you’re staying.

I recommend you choose from two popular walkabouts:

  • The Martha’s Vineyard Gingerbread Houses, a series of quaint Victorian cottages hidden in the center of Oak Bluffs
  • The Edgartown Harbor Light, the lighthouse that marks the entrance to Edgartown Harbor and Katama Bay 

Take a Drive to the Cliffs of Gayhead Martha’s Vineyard

At some point in the day, make one last drive down to the bottom left corner of the island to Aquinnah. It’s at the edge of the island are the famous clay cliffs of Gayhead. 

The colorful cliffs are a popular natural formation, and the lookout provides a magnificent view overlooking the ocean. There, you’ll also find Gay Head Lighthouse, situated on the westernmost point of the island.

Say Goodbye to MV

By now you may slowly be approaching the time you have to leave, so make sure to be on time for your ferry (unless your goal is to get stuck on the island).

For those who are walking on and off the ferry a major tip is to figure out which door the ferry unloads at, it can save a major amount of time since you don’t want to be stuck waiting for the second bus to come that takes you to the parking lot. 

Best Restaurants in Martha’s Vineyard

You’ll have plenty of opportunity to enjoy good food and drink while visiting Martha’s Vineyard. There are more restaurants and eateries than you’ll have time to try, so here are some of my favorites:

Sit-Down Restaurants

Very few places on the island take reservations, so take that into account when making dinner plans. 

Atria, Edgartown

Cuisine with worldwide influences (Mediterranean, Asian, Middle Eastern, to name a few). With various fine dining areas from the wraparound porch, main restaurant, and bar/lounge, this upscale restaurant is set within an 18th Century former Sea Captain’s home. Wine Spectator Magazine ranks its wine selection among the best in the world.

Nancy’s Seafood, Oak Bluffs

If you’re looking for fresh seafood, then look no further than Nancy’s Seafood. You’ll find a snack bar and take out on the first floor, and a full restaurant and lounge upstairs. Their outdoor seating is a great place to catch a panoramic sunset.

Bad Martha’s Brewery, Edgartown

A gardening-center-turned-brewery. Diners can enjoy trying flights of craft beer along with a variety of bar snacks. 

Jimmy Seas Pan Pasta, Oak Bluffs

Italian food, and one of my favorite places to dine on the island. The servings are humongous so I suggest sharing if you don’t arrive starving. 

Lookout Tavern, Oak Bluffs

All around American-style food. The restaurant looks out onto the ocean where the ferry comes in. If your group has picky eaters, I recommend this spot for you where you can enjoy fish tacos while they crush some chicken tenders. 

The Barn, Oak Bluffs

American style food. It is also the island’s bowling alley. 

Grab and Go’s

Fat Ronnie’s, Oak Bluffs

Constantly awarded one of the best places to find a burger on the island, Fat Ronnie’s is a small burger stand that has a subway style process of building your burger. The fried chicken sandwiches are also a delight. 

Coop De Ville, Oak Bluffs

A small wing shack that looks out onto the harbor. It has very limited spacing with its come-and-go picnic style seating. They have a variety of wing sauce flavors, the sweet chili wings are the best in my opinion. 

La Choza, Vineyard Haven

Mexican style cuisine similar to Chipotle. Many locals come here to pick up burritos, bowls, and tacos.  

Where to Stay in Martha’s Vineyard

Vineyard Haven Harbor, Martha’s Vineyard
(Photo: Jon Burke)

With any luck, you can extend your Martha’s Vineyard day trip to two or more days.

You’ll find a number of great options on when it comes to staying over in Martha’s Vineyard. Choose from a wide selection, from private rentals or AirBnB’s, to spacious vacation homes, beachfront cottages, and bed and breakfasts in Martha’s Vineyard.

Here are a few highly rated Martha’s Vineyard lodging options to consider for staying over:

  • In Vineyard Haven, you could rent a guest house at the highly rated Charles and Charles MV, which features an outdoor pool and complimentary bicycles. This inn is 15 minutes from the Vineyard Haven Ferry Terminal, and 2 miles from Mink Meadows Golf Course. 
  • The Oak Bluffs Inn offers well-appointed rooms, a scenic garden, and afternoon refreshments. It’s right in Oak Bluffs, just two minutes by car from the ferry and 5 minutes from Farm Neck Golf Club. 
  • In Edgartown, the Harbor View Hotel is on the coast and has as its name implies, has a view of the Edgartown lighthouse. You’ll find an onsite restaurant, two bars, and can opt to take sailing lessons. This is also one of the best inns on Martha’s Vineyard because it’s conveniently located just 10 minutes from Edgartown’s downtown.

Kelly House, Harborside Inn, and the Ashley Inn are also excellent lodging options.

Final Thoughts on Two Days in Martha’s Vineyard

With only a day or two to spend on Martha’s Vineyard, if you plan your visit well, you can see it’s possible to cover a lot of ground! But, don’t be surprised if this visit just whets your appetite. There’s plenty more to see and do on this charming island off the coast of Massachusetts. Once you get a taste for Martha’s Vineyard, chances are, you’ll want to visit again.

When do you plan to visit Martha’s Vineyard (again)? What are your favorite places to go and things to do on MV? Let us know in the comments below!

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Jackie Gately

Jackie Gately is a seasoned travel writer, photographer, and marketing consultant who is passionate about travel. She loves casual-luxury experiences, coastal getaways, cultural attractions, and local, wholesome food and wine pairings. A perfect day ends with her toes in the sand or by chasing the sunset with her camera--ideally both.