A Healthy Hedonist’s Guide to Martha’s Vineyard: The Best Restaurants, Markets and Ways to Work Off Your Meal


To say that Martha’s Vineyard is my happy place, as I often have, is an understatement. I’ve been coming to the island every summer since I was little. Basically, for as long as I can remember. And even in the peak of the August tourist season, it still holds so much hidden magic and local charm.

In addition to countless happy memories with my grandparents and extended family (not to mention, our elopement!), I owe the island big time for my love of food. While there are many best restaurants on Martha’s Vineyard that will keep you well-fed during a visit, the local agriculture and farming community are what make the island such a special place to cook.

A Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me Phoebe

I’ve already given you many line items from my vineyard culinary highlight reel, from the fresh Morning Glory Farm corn with basil butter to the island fresca soup I recreated from Red Cat Kitchen. Not to mention all the years of seared scallops, crispy yellowtail flounder, and baked bluefish from Edgartown Seafood.

Every summer, I vow to put together a Martha’s Vineyard travel guide for all my favorite farms, restaurants, and activities to work off your meal. Having finally done it, in this beast of a list, I feel the task was justifiably daunting. Hopefully, though, it will also be well worth the years of procrastination.

The island is only 100 square miles, but if you hop around, you can experience surprisingly varied landscapes over the course of a long weekend, from glassy ponds where you can pick your own clams for dinner, to rolling cow-studded hills. You can start the day surrounded by gothic cottages and end it beneath the red clay hills of Gay Head (skip to the bottom for a suggested 3-day itinerary). Since many of your decisions may depend on where you’re staying, I’ve included my suggestions for eateries and activities by the island’s three main towns: Edgartown, Oak Bluffs, and Vineyard Haven. Each has it’s own personality and demographic makeup.

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The half of the island west of Vineyard Haven, known as “up island,” is where the majority of the island’s farms are. This rural area is also home to many of the year-round population and artsy folk who sequester themselves away from the hum drum tourist centers.

Read on for the best restaurants on Martha’s Vineyard, delicacies of the island, and how to live vicariously through one of my perfect weekends here. And please reach out with any questions around an upcoming trip! I’m currently standing on call, looking out at the Nantucket Sound, and trying to decide which fishies I should pick up for dinner.

With health and hedonism,



If you’re coming from further afield than Boston or Providence, the easiest way to get to the island is to fly. The MVY airport is a mere 40 minutes in the air from JFK, and JetBlue and Delta now run regular direct flights during the summer season. On weekends, these tickets can be astronomically expensive, so book in advance. Also, avoid taking the last plane of the day. The weather is always a variable and it’s not uncommon for flights to get canceled due to fog or thunderstorms.

To travel by car, the most frequent ferry is operated by the Steamship Authority from Woods Hole, which runs pretty much every hour. During the summer, it’s best to book your vehicle passage well in advance. But you can also easily leave your car in the longterm parking lot. A shuttle runs like clockwork to the ferry terminal. But whether you’re leaving your car or taking it on the boat, it’s best to arrive 30 minutes in advance.

A Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me Phoebe

Smaller passenger ferries run out of New Bedford and Quonset from Memorial Day to Labor Day. And finally, as of a few years ago, Seastreak began running a weekend ferry from midtown Manhattan and New Jersey to Oak Bluffs. My dad likes to refer to this trip as “the party boat.” On Friday summer afternoons, you’ll see a lot of twenty-somethings getting frisky after work. And on the return home, a lot of them struggling from the previous night’s festivities. The boat is 5+ hours long, so while convenient, it’s not necessarily the cheapest or fastest way to the island. You’d also be wise to pack Dramamine, especially if you’re planning on being one of the above traveling with a hangover. The journey is relatively calm while you’re traveling through the Long Island sound (the first 2 hours from NYC), but once you hit the high seas, there’s likely to be a smattering of people bent over the side of the boat.

To get the most out of the island, I recommend having a car. But if you plan on sticking to the 3 main towns, you can easily travel by taxi (at an inflated rate), bus or bike.

When to visit Martha’s Vineyard

Since I fancy myself more of a local, my favorite time of year on the island is during the cooler off-season months. May and September are among the most gorgeous. Restaurants and shops will be open , but you’ll pretty much have the island hot spots to yourself.

If you’re traveling during the summer, I recommend planning around two of the most fun annual events: Illumination Night and the Ag Fair. Read on for more on those two.

Where to stay on Martha’s Vineyard

There are plenty of great hotels in Edgartown and Oak Bluffs. I recommend the former as a home base, but I’m slightly biased since I live a short ways away. There are, however, many benefits to renting a house with a kitchen if you’re staying for more than a quick weekend. If you’re planning on eating most of your meals at home and have a car, choose somewhere more secluded up island in Chilmark or Menemsha. For more access to the main towns, there are some great rental options in Katama Bay.

A Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me Phoebe


My parents’ house is a short 5 minute bike ride from downtown Edgartown, hence why I have more recommendations for this part of the island than any other (especially in the lunch department). Of all the towns, this one has the highest Lily Pulitzer dresses to people ratio. But I still love the feel of the old white shingled houses, many of which have been around since the 1800’s and include “widow’s walks” on the top floors so women could look out at the harbor to see if their whaling husbands had returned from sea.

There are a bunch of cute hotels right downtown in great proximity to the restaurants. Rent a bike ito explore some of the surrounding areas and beaches in Katama Bay.



**Behind the Bookstore

This cute little cafe opened up a few years ago, appropriately, behind the Edgartown Bookstore. It’s got a lot of healthy options, including an amazing grain bowl, avocado toast, and plenty of gluten-free baked goods inside the case. If you’re looking for a place to read the paper and enjoy a high quality coffee, the patio is very peaceful in the morning.

A Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me Phoebe


Another recent addition to the food scene, this gourmet food shop has prepared salads, tartines, and makings for a picnic meal. If you’re renting a house, you can also grab a few pantry items from the market side. Overall, a great option for to-go items that can be carried to a nearby beach or scenic location (like the Lighthouse). My favorites are the veggie burger on gluten-free bread, and the gluten-free peanut butter or ginger cookie.

Espresso Love

I have a sentimental softspot for this sandwich shop, which has been around since I was a teenager. They have great vegetarian options and gluten-free bread, though no as high end as Rosewater. I wouldn’t call it a destination in and of itself. But if you want a sandwich for the road, I’d recommend the Katama Chicken or The Mama veggie burger. There’s also a nice garden in back if you want to eat on the premises.

Lucky Hanks

On Upper Main Street, a stone’s throw from town, this little restaurant does a nice breakfast with all local ingredients. The cuisine is nothing to write home about, but it’s simple, seasonal and fresh–kind of like home cooking. A very good option to have in your back pocket if you want an unpretentious meal that won’t leave you feeling unworthy of your bikini the next day. I like getting the Farm Share, which is a mix of the chef’s daily veggie sides. It’s also much easier to get into than many of the restaurants right in downtown.

The Right Fork

This little diner is by the Katama airfield and you get to watch old planes take off and land during your meal. They make one of the best lobster rolls on the island and can do it on GF bread!

Black Sheep

Another clutch spot for nibbles. If you’re looking for charcuterie and local cheeses in town, this little shop is it.

**Morning Glory Farm

Now, if you want to buy local charcuterie and cheese, among many many other delicious things, I would highly recommend riding your bike up Edgartown-Tisbury road and checking out this market. Twenty years ago, MGF was nothing but a small family-owned farm stand. Now they’ve expanded and built a beautiful barn. While it lost a little charm in my eyes, all of their offerings have remained unchanged in their amazingness. And the good news is, now you no longer have to show up at 9am if you want to score a loaf of zucchini bread or strawberry-rhubarb pie. While the produce is some of the best on the island, I take my hat off to the baked goods. If you’re gluten-free, call 24 hours in advance and order a special GF zucchini bread. You won’t regret it.

If you want to stop in for lunch, they have a cold case of prepared foods. Also make sure to try their country pork pate and the Grey Barn cheeses, which they carry. The Prufrock is legendary.

Edgartown Seafood

This family-owned local seafood shop has the absolute best variety of fresh-caught fish on the island. Net Result in Vineyard Haven and Larson’s in Menemsha are also great. But for anyone in the Edgartown vicinity, there is no better place to shop for cooking provisions from the sea. I haven’t gotten takeout from there in years, but they also serve up all the fried favorites: clam and lobster rolls, oysters and such. The smoked bluefish pate from the case is a must.

A Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me PhoebeA Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me PhoebeA Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me Phoebe

The Fish House

If you’re willing to drive out towards the airport, this new fish store has some excellent prepared foods. On the gluten-free front, their poke bowl is epic and you can choose from seared or raw tuna or salmon. It’s a great option to take to the beach with you or on a hike.


Port Hunter

The closest thing MV has to a hipster Brooklyn restaurant, this space is a beautiful loft in downtown Edgartown, complete with a shuffleboard table, an excellent cocktail menu, and some creative eats. I love their veggie board, which includes beet tartar, mushroom pate and pickled fennel. It’s not a must for dinner, but a great place to get a drink afterwards when the bar scene picks up.

**The Covington

This restaurant is owned by the same team as Port Hunter across the street and is the upscale sister restaurant. They have delicious pastas with plenty of gluten-free options and some outdoor seating.

The Atlantic

This harbor-side restaurant is pretty run-of-the-mill in terms of vineyard offerings (a shrimp cocktail here, lobster roll with truffle fries there), but you can’t beat the view. It’s a great place to sit by the water and have a dozen oysters around sunset with a glass of wine.


I haven’t been in years, but Detente is still considered one of the best spots for refined fine dining on the island. I’m a casual gal, so I usually opt for State Road or Beach Road. But to each their own.

Atria Brick Cellar (Downstairs)

Sometimes you just want to take a break from the seafood frenzy and settle down with a big juicy burger. Atria opened up a more casual burger outpost in their basement that has a great wine cellar feel, and a nice wine list to match. Make sure to specify downstairs if making a reservation. Also, ask if there will be live music as it’s sometimes hard to hear your dinner companions, if so.

Drinks, Dancing & Nightlife

Back in my youth, there used to be only two places to let your hair down in Edgartown: The Wharf and the Seafood Shanty. Now, Port Hunter is the more upscale choice. All have live music occasionally, which is always a good time, especially when it’s the island’s 70’s cover band The Boogies!

For more cultured activities, make sure to check out the events schedule at The Old Whaling Church, which often doubles as a music venue and lecture hall. If you’re a theater and dance lover, The Vineyard Arts Project is an incubator for many of Broadway’s top talent. It’s a special and rare opportunity to see shows in their workshop phase before they graduate to grander, less intimate venues.


Though some MV visitors try to make shopping an athletic activity, you’ll find more to do on the outskirts of Edgartown than right on Main Street. Make sure to walk down North Water street to get your obligatory picture in front of the Lighthouse. If you’ve rented bikes for the day (highly recommended), take the ferry a hop, skip and a jump away to Chappaquiddick. The island is separated from mainland Edgartown by just a small breach in the sand bar on the south side of the harbor, but because it’s harder to get to by car, has remained pleasantly undeveloped. It’s a great place for a bike ride or to explore some of the less populated beaches during the peak summer season. You may have heard the name before, as this is where the infamous incident of Teddy Kennedy in the night occurred.

A Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me PhoebeA Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me Phoebe

For a slightly longer ride, head to South Beach in Katama Bay. You’ll pass the Boch mansion, which means a potential llama sighting. And if you want even more animal adventures, make a pit stop at The Farm Institute. This small sustainable farm does daily tours and educational workshops. You can also buy some of their grass fed beef and other butchered meat from the freezer.

At the end of Katama road, you’ll reach South Beach. If you like boogie boarding or jumping in the waves, and/or are a teenager, this is the best stretch of sand for you. Families with young children are probably a better fit for State Beach on the Sound-side, which has calmer waters. Which brings me to my favorite activity: a bike ride from Edgartown to Oak Bluffs.

This bike path along the North-Eastern side of the island follows State Beach along the coast and takes you over one of the islands most famous cinematic landmarks: the Jaws bridge. Jumping off of it is an island tradition, and it makes for a perfect pit stop on the 7-mile ride.

A Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me Phoebe

There are also some lovely walks near town: Sheriff’s Meadow is just past the lighthouse, and Caroline Tuttle Preserve is a short drive or bike ride from downtown. If you have a car, Felix Neck is a great option between Edgartown and Vineyard Haven.


During the summers, when most ferry services run out of OB, the town becomes one of the island’s most accessible (i.e. touristy). This can often mean packed sidewalks on Circuit Avenue, the main thoroughfare for restaurants and island curiosities. But it’s worth a visit regardless for a few must-eat items (including the island’s BEST chowder), and colorful gingerbread houses that line the historic back alleyways.

The town is also the island’s most diverse, with an interesting racial history that led many to question whether or not the Obamas would stay on this side of the island when he first started coming here.



Slice of Life

This little cafe at the end of Circuit Ave has some of the best sandwiches and salads around. I’m partial to the Seared Salmon Salad, and back when I could eat it, the Fried Green Tomato BLT. They make all the bread in-house and it’s extraordinary (sadly, no gluten-free options just yet). For a casual bite at night, Slice is also open for dinner.

**Martha’s Vineyard Chowder Company

It’s on my cooking bucket list to recreate the chowder at this pub-like outpost right on Main Street. The broth is gluten-free (meaning thin, not gluey) and each bowl is packed with veggies (leeks, celery, onions, shallots) and real meaty clams. We have a tradition of biking from Edgartown and rewarding ourselves with a bowl of chowder, side of fries, and a cider before making the haul back.

A Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me Phoebe


**The Red Cat at Ken & Beck

For a casual, imaginative dinner, Chef Ben DeForest always delivers. The menu changes daily, allowing for seasonal finds. One item you’ll always see though is the Island Fresca Soup, which I often recreate at home. It’s summer in a bowl, and worth a trip just for that.

Sweet Life Cafe

Recently acquired by the team behind Detente in Edgartown, Sweet Life Cafe is the best spot for an upscale meal in Oak Bluffs. The outdoor patio lends a lovely ambiance, making it a great choice for a special meal out on the town.


This is a new addition that opened during Covid but always has healthy, homey options in a pleasant environment. It’s definitely a more casual vibe, but also more upscale than the chowder house.


This outdoor eatery a little ways outside of town is perfect for a beautiful night with a big group. You can order at the counter and set up shop at one of the fire pits on the lawn out front. There are also plenty of lawn games to pass the time if the food and rum cocktails are not distraction enough.

Drinks, Dancing & Nightlife

Off Shore Ale Co.

Most of the bars in OB have a distinctly bro-y vibe. If you want to party hard, try Nancy’s or the Lamp post. For a more relaxed evening of drinking (i.e. more my speed), this brew pub is one of the old great hangouts of the island. The floor is covered with peanut shells and the craft beer on tap is MV’s best.

Backdoor Donuts

One of the more famous foodie traditions on the island is to stand in the back alleyway outside MV Bakery and wait for their after hours donut special. This used to happen only after the bars had closed, but since it became a phenomenon that spread beyond drunk college students, the bakery decided to make it more of a legit part of their commerce. The line will start up at around 7pm and shut down just before 1am. You can smell the deep fried dough and powdered sugar from the other side of town–the best marketing you could ask for.


When I have guests in town, I always make sure to take them to the old MV Camp Ground Meeting Association: a cluster of brightly colored gingerbread homes from the 1800’s arranged around an open-air Tabernacle. My favorite aspect of these houses, besides their scale and color scheme (a Pantone book on crack), is that many have a tiny doll-sized replica in the backyard. If I was a little girl, these mini versions would be my ideal play house.

If you’re wondering when to go to Oak Bluffs, consider planning your trip around Illumination Night. Once a summer, the town goes completely dark, except for the houses around the tabernacle, who string up lanterns that have been passed down from generation to generation, illuminating their houses like a Christmas tree. It’s always a clusterfuck. But quite a sight if you’ve never been.

Finally, calling all Dispatch fans!! Don’t miss the Flying Horses carousel in the center of town. You may not have the opportunity to steel a ring, but the lyrics will make sense, at least. And if you have no idea what I’m talking about, just check it out anyway. It’s the oldest operating carousel in the country and pretty cool.

Because it’s more of a tourist hub, there aren’t any great markets right in Oak Bluffs. The closest is Cronig’s in Vineyard Haven (a great option).

A Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me Phoebe

My favorite activity is riding my bike up beach road from Edgartown to Oak Bluffs. If you have a car there are also some wonderful walks outside of town. Checkout Trade Winds trail right near Farm Neck golf and tennis club.


Locals refer to the Western side of Martha’s Vineyard–the smaller towns of Menemsha, Chilmark, Aquinnah and Tisbury–as “Up Island.” This is where the landscape becomes more sprawling, and is home to the majority of the island’s farms. If you have a car, it’s worth taking a drive up State Road to experience the lookouts over Menemsha pond, and back down through the enchanted forests of Middle Road, where you can stop at various farm stands.

Vineyard Haven was a dry town until a few years ago. And that legacy is one of the reasons why VH has remained fairly mellow and less of a tourist zone compared to Oak Bluffs and Edgartown, which have varied bars and nightlife.



**Art Cliff Cafe

You may have to stand on line for 1+ hours to get into this small divey diner. But it will be well worth the wait. It’s the best brunch on the island, and quite possibly the world. The menu has gotten even longer in recent years, but you can’t go wrong. The cod cakes and tex-mex specialties are always delicious. But I’m partial to whatever seasonal items are listed on the specials board. There’s usually a great hash with Morning Glory produce. The soups and chowders are always wonderful as well. And for those who can partake, there’s usually a mouth watering scone or muffin involved.

A Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me Phoebe

Scottish Bake House

This cottage lunch spot is a little further inland from Vineyard Haven town, so I never go out of my way to make a stop there, but for those interested in some healthy and gluten-free options, SBH has a lot to choose from.

The Net Result

Down the street from Art Cliff Cafe, The Net Result is one of the best fish markets on the island. They also sell an array of crispy fried seafood and sushi, which people enjoy on the picnic tables out front.

Larson’s Fish Market

In the evening, it’s a tradition to picnic on Menemsha Beach and watch the sun set. Most people try to get there before this local fish shop closes so that they can get provisions–oysters, lobster rolls, bluefish pate–to eat in the sand. If you live up island, this is also the best seafood shop for all your at-home meals.

Little House Cafe

Another great lunch spot with gluten-free options. I am partial to their fish tacos!

Chilmark General Store

The underappreciated hub of great pizza, Chilmark General Store is perfect for grabbing basic provisions for your home kitchen if you’re staying up island or an easy lunch or dinner takeaway for the beach. They have both cauliflower and GF crust! I prefer the cauli. The topping combos are very fun and all are delicious.

The Larder

This partner establishment to the Good Farm has gluten-free fried chicken that can be ordered in advance. If you go to the Farmer’s Market on Wednesday or Saturday, you can also find it there!


**State Road

Despite all the amazing produce and local purveyors on the island, it took a while to get a truly delicious farm-to-table restaurant that survived year-round. State Road was the first, and remains the most popular. The cuisine and ambiance are casual, despite it being one of the best places to eat on the island. Call a few weeks in advance for a reservation, especially if you plan on dining over the weekend. Breakfast and brunch tends to be a better bet for getting seated without one, and their bluefish or duck hash specials never disappoint. During the week they also have an epic burger night. If you happen to be on island during the cooler months, their fireplace makes the tavern feel extra cozy.

Beach Road

The sister restaurant to State Road is closer to the center of VH town, just a stones throw from Net Result and Art Cliff Cafe by the shore. It’s a similar menu to State Road, with more of an emphasis on seafood, and includes two monster lobster rolls. It’s easier to get a reservation here as it’s a larger space (and includes a private area with a big group table).

Chilmark Tavern

A go-to spot for a casual, unpretentious meal, especially for those who live in Chilmark or further up island. It’s a great option if you can’t get into State Road and don’t want to travel to one of the bigger towns.

The Homeport

Right at the foot of Menemsha’s little fishing village, this lobster spot is a bit of a tourist attraction. But it’s the best place on the island for an amazing fresh lobster dinner with a beautiful view of the water. If you’re going to watch the sunset on the beach and want a more substantial meal afterwards, this is a great option.

Outtermost Inn

This is where my husband and I dined after we eloped, so it has a special sentimental value. There’s no where that has a more romantic ambience. The inn and restaurant are owned by Hugh Taylor, brother to James Taylor. He runs the family business with his wife and if you stay the night, you might find his nieces are your waitstaff the next morning. The food is always solid though nothing terribly creative. Book for around sunset so you can take in the deer frolicking in the lawn out front.


As mentioned above, there isn’t a bar scene on this side of the island. But there are plenty of cultural happenings to keep you busy. Poetry readings and art openings happen periodically. The Chilmark Community Center usually has a host of events featuring famous residents of the island, including the MV Film Festival.


On Saturday mornings, all the local purveyors gather at the Tisbury Farmer’s Market. It pays to get there early (before 10am), especially if you want to skip the lines. Even if you’re not shopping for produce, there’s a great array of stands, including locally made soaps, ice coffee, and floral arrangements. The market moved in COVID times to the Ag Hall and appears to be remaining there. I like ordering lunch in advance from Good Farm/Komrade (GF fried chicken!) or Kitchen Porch. The Salt Rock Chocolate ladies are also not to be missed. Make sure to order two days in advance of the market. They will be gone within the first 15 minutes!

During the day, drive up to Gay Head where you can see the big lighthouse and experience the clay cliffs on the beach. You may get to take in more sights than you bargained for if you wander to the nude portion, perhaps that’s an equally fun part of the scenery.

On your way back to town, drive along Middle Road and stop at some of the farm stands along the way. Beetlebung is open to the public. Mermaid Farm has a self-serve fridge with their fresh cheeses. If you see fresh ricotta, yogurt or a Lassi, grab it. Over on State Road, you can stop by Grey Barn, the island’s most famous creamery. They have occasional tours, so check out the schedule in advance.

A Healthy Hedonist's Guide to Martha's Vineyard: The Best Restaurants, Markets, Farms, and Activities to Work Off Your Meal. Plus tips on when to go, where to stay and how to get there | Feed Me Phoebe

As mentioned above, one of the best evening activities is watching the sun set over Menemsha Beach. Pack a cooler of rose and a few blankets (it gets chilly at night), and set up shop on the beach. If you want to find parking nearby, you’ll want to set out early. Otherwise, you may have to leave your car on the shoulder on the way into town. When the sun finally dips below the horizon line, everyone claps and fills me with so many warm fuzzy feelings.

Finally, if you can, plan your trip around the annual Ag Fair. It’s truly the most memorable weekend on the island. You’ll get your farm animal fix at the pig and draft horse races, see who wins the blue ribbon for best ear of corn or pie, and experience some unconventional island athletes flex their muscles in the skillet toss and lumberjack competitions.


This trip assumes that you’ll be arriving Friday evening and departing Monday mid-day. I’ve also recommended the order of activities based on a home base in Edgartown, but they can easily be adjusted depending on where you’re staying. One day requires a car, which I would recommend to experience the sites up island. There are plenty of taxi services that can take you, but it would probably be cheaper just to do a rental for the day. If you’re not going to be visiting the Farmer’s Market on Saturday morning, you can swap days 2 and 3. If you have a car both days, you can also break up the up island adventure into two parts so that you’re not having dinner in Edgartown two nights in a row (return up island for sun set and dinner at State Road the third night). Also, this plan assumes that you’ll only be eating out, not cooking. And it definitely requires a lot of eating.

Day 1, evening arrival

>Arrive in Edgartown in the evening, and stroll down N Water Street to the Lighthouse.
>Enjoy sunset oysters at The Atlantic by the harbor.
>Grab dinner somewhere in town. I recommend The Covington, followed by a cocktail at Port Hunter across the street for some live music.

Day 2, driving up island

>Wake up early and begin your drive up Edgartown-Tisbury Road to the Tisbury Farmer’s Market.
>Explore the stalls and enjoy an ice coffee. Pick up GF fried chicken and other picnic snacks for the road.
>Continue driving up Middle Road and stop at various farm stands for more nibbles. (An optional detour to Menemsha for a lobster roll from Larsons)
>Spend the day at the beach in Aquinnah. Check out the cliffs of Gay Head and the Lighthouse.
>Drive back down State Road and take some pictures of the look out above Menemsha Pond. Stop in at Grey Barn for a cheese sample.
>Circle back to Menemsha in time to watch the sun set. Pick up some blue fish pate and/or oysters at Larsons.
>Grab a nice dinner at State Road on the way back down island.

Day 3, bike tour

>Rent bikes somewhere in town.
>Grab a morning coffee and gluten-free pastry at Behind the Bookstore, or bike a short ways to Morning Glory Farm and enjoy a loaf of zucchini bread on a picnic table.
>Continue along State Beach and pit stop for a morning swim, a few hours of beach relaxation, or a plunge off the Jaws Bridge.
>Arrive in Oak Bluffs in time for lunch and enjoy a bowl of chowder at MV Chowder Co.
>Pop into the Flying Horses, then stroll down Circuit Ave until you reach the entrance for the Tabernacle (one of the alleys on your right, if you’re coming from Main Street).
>Bike back towards Edgartown. If your legs still have some juice in them, continue up Katama Road to South Beach. Keep an eye out for lawn llamas on the way. Go for a stroll or boogie board in the waves. Pop into The Farm Institute to meet their animals on the way back.
>Have dinner in Edgartown, or take a car back to OB for dinner at Red Cat Kitchen.

Day 4, early afternoon departure

>Arrive early for breakfast at Art Cliff Cafe before you leave!
>Stroll up Main Street and duck into Bunch of Grapes for some books.

Are you a Martha’s Vineyard lover? Feel free to include any insider tips I may have missed in the comments below! 

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