A long weekend to remember. The name “Martha’s Vineyard,” or just “The Vineyard,” evokes lobster, beaches, harbors that once hosted tall-masted whalers, and a rich farming, fishing and whaling history. Because of this it has thriving and independent grassroots locals who focus on innovative ways to use their resources. The focus here is all on local food. Having been to Martha’s Vineyard twice, I’ve become familiar with the island’s many personalities: preppy Edgartown, Victorian Oak Bluffs, calmer Vineyard Haven, and wild and untouched Menemsha. The island is full of rolling hills, stone walls, and there is not a single McDonald’s, strip mall, or big-box store in sight. If you’re looking to spend 2 to 3 days on Martha’s Vineyard, this itinerary is a picture-perfect postcard of lighthouses and gingerbread cottages. Whether it’s your first or your tenth time on The Vineyard, this is summer at its best—a long weekend getaway in an idyllic and down-to-earth setting.
FAQs:
How many days do you need on Martha’s Vineyard?
Anywhere from 1 day to a full month. It really depends how much time you have and what your goal is. You can get an idea of the island with a day trip, but to truly unwind and understand the local way of living, a longer 5+ day vacation is needed. Understanding that not everyone has the luxury of time, you can very easily spent to 2-3 days on Martha’s Vineyard and still get a sense of the land, culture, people and experience, all the while visiting iconic stops as outlined below.
How long does it take to drive around Martha’s Vineyard?
The island is very small, so you can get around in a full 45 minutes by car.
Do I need a car on Martha’s Vineyard?
You will read places that say you don’t need a car, but you need one. You can bike everywhere if you’d like or take the public bus (which includes bike racks where you can stack your bike), but if you’re looking to cover the whole island, a car is best. The first time I visited “The Vineyard,” my mother and I only had bike. The second time I visited Martha’s Vineyard with my husband Patrick, I had bikes and a car. I preferred the latter. Much more flexibility to see things during with just 2-3 days on Martha’s Vineyard.
How do I get to Martha’s Vineyard?
You could fly, but then you’d have to uber, rent a car, bike etc to get around. The best way is via the high speed ferry that leaves from Woods Hole and takes you to Vineyard Haven. The ride is only 45 minutes, very close compared to Nantucket. And you can bring your car aboard as well. Bringing the car on the ferry costs a hefty premium, but it’s worth it! Between the time you save, the flexibility you have in going places and the cost of renting bikes or cars on island, the car pays for itself.
Where should I stay in Martha’s Vineyard?
If you know me – I’m a boutique hotel sort of a girl. I like the intimate stays with the local touches, homey owners, home-cooked meals, and attention to detail that only local business owners can share with you. They end up treating you like family and you feel like you got to know the people of a place. There are two places in Martha’s Vineyard I would recommend to stay in: Nobnocket Boutique Inn in Vineyard Haven or the Hobknob hotel in Edgartown.
Quick Navigation
~ Day 1: Vineyard Haven & Edgartown ~
1. Lunch: Waterside Market
After an early AM wake up call, a 4 hour drive from Connecticut, to Woods Hole and a 45 minute ferry, our stomachs were growling. Our local inn gave us a lunch recommendation nearby, so we decided to visit Waterside Market in the main town of Vineyard Haven. Recommendations from local inn’s in Martha’s Vineyard are NEVER a miss. When it comes to food, they know their stuff. My mom had the avocado toast and I had the skinny wrap with eggs, avocado and spinach. Everything was so fresh, so light, so scrumptious…and ohhh my, flavorful. When was the last time you had a corn kernel or a slice of tomato ALONE and tasted it’s distinct flavor without dressing or anything needed on top? For me, the last time was in Europe. We couldn’t not top it off with a little cookie to give us energy for the rest of the day.
2. Afternoon: Explore Vineyard Haven
After lunch we digested a bit by strolling around Vineyard Haven and strolled past ice cream shops, ancient movie theaters, art galleries, the Vineyard Playhouse, antique stores, and vibrant stores burning incense and selling souvenirs, earrings, and bracelets. The town is small with the main attraction being the ferry coming in and out so it can feel gridlocked at times, but there are plenty of shops to keep one busy.
Keep Your Eyes Peeled…Or Don’t
Gobble gobble is a sound that is frequently associated with Martha’s Vineyard. It is not uncommon to come across a turkey casually crossing the street, taking up a street, or sitting in a tree on Skiff Avenue. Vineyard Haven, especially, is known for having an abundance of turkeys wandering the town. See the turkey in the above picture?
3. Afternoon: Visit Oak Bluffs
Next up, we hopped on our complimentary bikes from our inn and headed toward Edgartown. The island is basically created for cyclists, so there are cycling paths built into almost every road making it very safe. The road to Edgartown includes stops at Oak Bluffs, followed by Jaw Bridge in front of State Beach, and ending at Edgartown. The bike ride is a simple 45 minute scenic oceanside route (one way) on a completely flat road. Don’t pedal too hard today, take it easy. With only 2-3 days on Martha’s Vineyard we needed to pace ourselves if we were going to see everything! Tomorrow will be your big cycling day so save your legs.
Walking Martha’s Vineyard Gingerbread Cottages in Oak Bluffs
First stop: Oak Bluffs (15 minutes by bike from Vineyard Haven). It didn’t take long for us to pick up the distinct contrast between Oak Bluffs and the surrounding Martha’s Vineyard towns. If there is one place you must see if you only have 2-3 days on Martha’s Vineyard, it’s Oak Bluffs. Oak Bluffs has been home to the African American community for over a century. The first African Americans to settle in Martha’s Vineyard were indentured servants, runaway slaves, and whalers. When slavery was finally abolished in the 18th and 19th century, the African American community settled into Oak Bluffs and made it their home. This settlement was just the start of a thriving and unique community on Martha’s Vineyard with the Victorian style Oak Bluffs gingerbread cottages were at the heart of it. It’s a place where you chat with neighbors, catch up on your reading, or enjoy a glass of iced tea.
While in Oak Bluffs, don’t forget to visit Flying Horses, the oldest continuously operating carousel in the nation built in 1876! And if you’re hungry, head to the over 70 year old Back Door Donuts. It got it’s name from the old sales tradition they had of serving donuts at any hour of the day from the back door, including 4 am. When you wanted it, Peter’s team obliged.
4. Afternoon: Stop by Jaws Bridge & State Beach
It is tradition to memorialize a visit to Martha’s Vineyard with jump off Jaws Bridge. As you bike by the bridge connecting Oak Bluffs to Edgartown, you will always see a line of people lined up to jump off. This is the famous scene where the movie Jaws was filmed. If, like me, you have a fear of sharks, I wouldn’t recommend you swim much in Martha’s Vineyard as it’s notorious for it’s sharks along with Nantucket. So you can just watch from the sidelines as brave souls thrust themselves into the water. Additionally, it’s not safe to jump off the bridge, in fact it’s technically illegal due to strong currents and tides that can pull swimmers under. If you’re looking for a quick dip and go, I’d suggest you stop right next door at State Beach instead. Much safer!
5. Afternoon: Explore Edgartown
5 Essential Things to Do in Edgartown, Martha’s Vineyard
We finally made it to Edgartown, the most vibrant and lively of the towns on Martha’s Vineyard. A stroll through Edgartown, the first colonial settlement in Martha’s Vineyard settled by whaling captains, is essential to understanding the vineyard’s culture and history. To this day Edgartown is considered one of the world’s great yachting centers. Here we spent the afternoon wandering the streets, getting to know local store owners and businesses, and catching a late night sunset from Edgartown Beach and lighthouse.
6. Dinner: 19 Raw Oyster Bar
7 Edgartown Locals Who Bring Martha’s Vineyard to Life
A broad spectrum of innovative seafood attracts a steady stream of people and dogs (it’s dog friendly!) right off of Main Street to 19 Raw Oyster Bar. Pat and I took a seat at the front patio and ordered a hand-craft cocktail before diving into the menu. 19 Raw Oyster has a very chill vibe, wooden bar like tables, high top chairs, good music, industrial like accents, space heaters, and good, authentic, and quintessentially friendly New England service. We started with an appetizer of various locally-sourced oysters that acknowledged local Chef Joe Monteiro’s primary reason for opening his restaurant on the island. The menu doesn’t stop at oysters though, 19 Raw Oyster offers items to please any palate. From crudos to small tapas like plates and entrees, it will appease most anyone’s hunger needs.
~ Day 2: West Tisbury, Menemsha, The Cliffs ~
1. Morning: West Tisbury Farmer’s Market
Hope your legs aren’t too tired from yesterday’s biking because today is the most of it! Farm stands are an art form on Martha’s Vineyard. One could drive or bike the island all day picking up morning glory muffins, homemade feta cheese, lamb grazed on Chilmark hillsides, meaty Bibb lettuces the size of hubcaps, cranberry apple pies, and bouncing bouquets of field-grown flowers, even locally harvested sea salt. And that’s just the beginning. The farming culture is something of a dream here. Not only are farmers the celebrities on the island, but some of the farms – like Allen Sheep Farm and Beetlebung Farm – have been here for more than 6 generations.
Because of this rich farming and fishing heritage, all food in Martha’s Vineyard is focused around the islands treasured ingredients. There’s a reason it’s known as the land of milk and honey, of bluefish and kale. A bounty of crops makes every season special. Everything is grown locally. The coffee is from Chilmark coffees, the dairy is from Mermaid Farm or The Gray Barns, the local honey. Kale is a bit of an inside joke on Martha’s Vineyard, since there is plenty of the vegetable all year round.
That’s why a trip to the weekly Saturday morning farmers market in West Tisbury is a must when on the island. We took the public bus from Vineyard Haven, which allows you to stack your bikes in the front, and drove by gorgeous scenery, rolling hills, stonewalls, and herds of cows towards West Tisbury’s farmers market.
Meet the West Tisbury Farmers Market’s Artisans & Farmers
What makes Up-Island so special is its stark contrast to its Northern cities. Rolling hills of century old farms, forests, and private beaches give it a quieter more quaint vibe. One of the most notable gatherings held Up-Island in the town of West Tisbury is the twice weekly West Tisbury Farmers Market, a can’t miss event if you want to experience the true locals of Martha’s Vineyard. The event is held Wednesdays and Saturdays in July and August at the iconic Grange Hall. But when you come here, you aren’t just visiting any farmers market, you are listening to the stories of how these local artisans source the produce and make it or pluck it themselves. A local band was playing and locals sat on picnic tables listening and some even dancing to the live music. It was a very genuine and unique feel I hadn’t felt yet on the Vineyard.
2. Morning: Mermaid Farm & Dairy
We picked up our bikes and left the West Tisbury farmers market in search of other farm stands. We drove down Middle Road, which is known for it’s collection of farm stands. We stopped by Mermaid Farm & Dairy. Since Mermaid farm is known for their dairy, you should get a batch of their raw milk, duck eggs, or…my favorite if they have…their mango lassis made with farm yogurt – divine!! Martha’s Vineyard, like many farms on the Northeast, run a very trustworthy business. They trust that if you pick something from their stand, you will leave them the right amount of cash for that item in their money box. No one is there to check and make sure you pay for the item, it works on an honor system. It gives an innocence and sense of safety to the island that brings one comfort, as if you’re considered a part of this local community.
3. Morning: Allen Farm Sheep & Wool Company
Surrounded by massive stone walls, the grounds of Allen Farm Sheep & Wool Company are a sight to behold. Allen Farm’s white, brown, and black sheep have been grazing on wind-swept grass spiced with salty Clarissa since 1760! Say hello to some of the lamb and sheep grazing on the rolling hills before walking inside the gift shop. You’ll swoon over the vibrant selection of handmade sweaters and other items for sale.
If you’re in need of a pick me up on the way, stop by Chilmark’s chocolate for a box of their selection chocolates rich in fragrances and spices.
4. Afternoon: Menemsha
Menemsha, Martha’s Vineyard: An Unchanged Place
We pedal all the way to lunch in the small, but mighty, fishing village of Menemsha. This is probably my favorite stop out of all during our 2-3 days on Martha’s Vineyard. Menemsha has a strong sense of place, even though it may not have much going on. Menemsha is also known as “Amity Island” in the famous movies Jaws. This is where the majority of the films scenes were shot so you’ll see references of that throughout. Fish markets line up the weathered gray dock, where fishing boats tie up to unload or fill their gas tanks. We walk by fishing shacks and cedar shakes weathered as gray as the beards of ancient mariners. The walk unveils 3 famous eatery institutions that people from all over the island flock to: The Galley, a take out establishment that specializes in chowder, soft-serve ice cream, and lobster, and Larsen’s Fish Market for fresh fish, or The Bite for what is known as the best fried clams on the island. The village also has a few art stores, antique shops, and clothing shops, but it’s the fishing village and food scene that draws the crowd. There’s a tiny beach just off to the side, but we’re here for the lobster salad from Menemsha Galley.
5. Lunch: Menemsha Galley
Menemsha, Martha’s Vineyard: An Unchanged Place
We sit in the shaded petite wooden shack in the corner of the port and watch as the fishing boats come in and out of the port with the fresh catch of the day. Still hungry? Go back for their soft serve ice cream. With a little Menemsha breeze in our hair and the putt-putt of lobster boats in our ears, we are here to experience a down-to-earth part of the island.
6. Afternoon: Aquinnah Cliffs, aka Gay Head Cliffs & Lighthouse
Our last and final stop is to Aquinnah Cliffs and Gay Head. To get there we take a bike ferry that takes you between Menemsha and Gay Head for just $4 one way or $7 round trip. The boat is exactly that. A miniature ferry that carries bikes across this small sound to the other side of the island. The journey is about 3 minutes, but is the only way to get to Aquinnah Cliffs and Gay Head by bike, unless you want to do a super long bike ride along busy State Road.
Now…what started off as a very flat road along miles and miles of beach, feel free to stop by for a swim if you dare, seemed straight forward. Until we hit the massive hills. I mean, I should’ve expected this. It’s called Aquinnah CLIFFS. How else could we reach the cliff if not by BIKING to the top of it. Yikes…our legs were destroyed. Remember to come prepared with plenty and I mean plenty of water, especially on a hot summers day. But the view at the top is worth it. When my mom reached the top by bike, she received an applause from people around her – I mean it was quite impressive!
Aquinnah is as up-island, or South, as you can get on Martha’s Vineyard. Everyone flocks here for a view of the windswept 150 ft cliffs that form a jagged face down to the Atlantic into the 5-mile long beach. They say that the beach area directly below the cliffs is off-limits, but the truth is you’ll see even in my picture above, somehow people still make it down there. As you walk up to the viewing center, the pedestrian street is lined with shops and informations booths maintained by the Wampanoag Native Americans. It’s a great place to learn about their stories and history.
There’s a trail you can take from the viewing point all the way above the cliffs that takes you to Gay Head Lighthouse, a red brick lighthouse that’s been around since 1844. Like most lighthouses on the Northeast, it’s already been moved 150 feet inwards to protect it from erosion. But Sveva – once you’re up island, how do you get back down island? Well – you bike! Just kidding, absolutely not. From you here, you take the public bus again that allows you to stack your bikes in the front and you head back to Vineyard Haven.
7. Dinner: State Road Restaurant
At this point, trust me when I say that you’ve worked up quite an appetite after all that biking. We decided to reward ourselves with a bike ride—just kidding – a DRIVE—to State Road MV. If you’re eating at the restaurant, BYOB and you’ll need a reservation. State Road Restaurant is surrounded by farms and the menu is straight farm-to-table. There’s an option for patio seating or an antique filled farmhouse with a fireplace as a centerpiece.
If you plan on doing takeout like we did, prepare for a long wait. The place is jam packed, but the burger is worth the wait. The burger selection here is also one-of-a-kind, just like the rest of Martha’s Vineyard’s food-scene! We ordered the classic State Road Burger ($16), but you can experiment and order the Lamb burger ($18), Turkey burger ($16), veggie burger ($14) or even switch burgers out for their Duck sloppy joe ($16) or chicken pot pie ($18). I heard the ricotta blueberry pancakes and egg sandwiches for breakfast are amazing too…your pick if you choose to go back!
We took our to-go burgers and enjoyed them with some MVY local wine on the wrap around front porch of our Edgartown inn.
~ Day 3: Hike & Beach ~
1. Breakfast: Behind the Bookstore
7 Edgartown Locals Who Bring Martha’s Vineyard to Life
I think we’ve biked enough the last 2 days, you probably can’t feel your legs anymore. So day 3 in Martha’s Vineyard is a driving day, mixed in with a gentle and moderate hike. You’ll surprisingly wake up with an empty stomach, so walk on over to Behind the Bookstore and load up before taking on a nice morning hike. Hidden behind the bookstore Edgartown Books, the locale was started by bookstore owners Jeffrey and Joyce Sudikoffis. Make your way through a small cobblestone alley, past some greenery, and you’ll find yourself in an outdoor eatery with tables and chairs scattered beneath a ceiling draped in shade sails. As you step into it, you feel like you’re entering a sultan’s harem with a secret garden. Some of their breakfast specialties include their breakfast sandwich, yogurt and granola, and famous caramelized grapefruit.
2. Morning: Cedar Tree Neck Trail
Cedar Tree Neck Trail’s 2-mile hike has it all: beach, forest, and wetlands. There are 400 acres of land in this West Tisbury Nature Preserve. During the hike, you pass by Cedar Tree Neck Pond before reaching a seaside stroll above the bluffs. From the bluffs you can see views of Cape Cod and Elizabeth Island. You can descend onto the shores of the rocky beach and walk for a few miles or turn around and loop back. Just note that because it is a nature preserve, swimming is forbidden in both the pond and the sea.
3. Lunch: Garde East
7 Edgartown Locals Who Bring Martha’s Vineyard to Life
At this point, we racked up an appetite after sweating it out on our morning hike. Because all the food in Martha’s Vineyard is locally grown, you’ll have forgotten that you just ate a few hours ago. The food is so light and sits so well, you’ll always be hungry for more, and that’s a good thing on an island with so much good food. After our hike, we felt like we had earned a well-deserved meal at one of the only 2 waterfront restaurants in Vineyard Haven located in front of a marina full of yachts.
The French American menu at Garde East changes every week to reflect seasonal and local cuisine. We started with a beautiful farmers salad and duck rillettes. The farmers salad was a beautiful representation of the Martha’s Vineyard terroir. The presentation of the whole roasted fish drizzled with green sauce was the highlight of my meal. The waiter had brought Pat a sumptuous-looking barbecued chicken with a side of locally roasted carrots. Once we were done, we topped our meal off with a key lime dessert.
4. Afternoon: Katama Beach
Before catching a late afternoon ferry, we decided to go unwind at Katama Beach, also known as South Beach. It had been a jam packed and eventful 2 to 3 days on Martha’s Vineyard, so there was no better way to close out our long weekend itinerary than with a good meal and a nap at one of the prettiest beaches on Martha’s Vineyard. Katama Beach is located just 3 miles South of Edgartown. The beach attracts a young surf crowd due to it’s rough waves, barrier beach and high dunes.
We unpacked our turkish towel from our MV canvas bag, both from Slate in Edgartown, and just laid in the sand for a few hours dozing off. Checking our phones every now and then to make sure we wouldn’t miss our ferry. You won’t see many people in the water on rough days due to the powerful waves, and of course, sharks. But there are areas that are safe and lifeguarded for those interested in a swim. Luckily the breeze is so strong on the beach, you really don’t need to go in for a dip.
And there you have it – the ultimate 2 to 3 days on Martha’s Vineyard itinerary. From charming towns and scenic hikes to delicious dining and relaxing beach days, this itinerary has everything you need for a memorable getaway. So pack your bags, hit the road, and get ready to experience the beauty and charm of Martha’s Vineyard firsthand.
~ 2-3 Days on Martha’s Vineyard: Long Weekend Itinerary Map ~
~ Important Things to Keep In Mind ~
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