Which of the 6 Martha’s Winery Cities is Finest for You? A Information.

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Unspoiled seaside settings, rolling hills, and a relaxed tempo have lengthy attracted guests to the shores of Martha’s Winery. That is, in any case, a small island; a splendidly rural place to take pleasure in drives on nation roads. Its 87 sq. miles is an oasis of old-world attraction and pure magnificence in equal measure, with each a summer time season and year-round inhabitants.

Situated about 4 miles off the southeast coast of Cape Cod, Massachusetts, quaint cities and contemporary ocean breezes carry hordes of tourists yearly. The 2 famously photogenic cities of Martha’s Winery embody Oak Bluffs, with its colourful Victorian gingerbread homes, and Edgartown, with its stately brick houses.

The island of Martha’s Winery is split into two principal sections: the extra populated “down-island” cities of Winery Haven, Oak Bluffs, and Edgartown, and the extra rural “up-island” cities of West Tisbury, Chilmark, and Aquinnah. Dwelling year-round fishermen and farmers, creatives and entrepreneurs, tradesmen and lecturers — and a LOT of attorneys and surgeons in the summertime — a powerful sense of neighborhood and distinctive character is the draw for a lot of to make a house right here. 

Martha’s Winery is a good place to partake within the easy pleasures of strolling, biking, fishing, boating, crabbing, beachcombing, grilling, or just studying a e-book underneath a tree. 

And right here’s one thing to know: regardless of its title, Martha’s Winery doesn’t really include any vineyards, a lot to the chagrin of wine fanatics (and my husband particularly). However concern not, there’s loads of wine to drink, and lots of of different issues to do in these six great Martha’s Winery cities.

A crowd of people enjoying drinks at an outdoor bar underneath umbrellas, next to a tall pale blue Victorian house with a wraparound porch.

Finest Cities on Martha’s Winery

What are the very best Martha’s Winery cities for households? 

Each single city on Martha’s Winery could be very family-friendly, however Oak Bluffs has some pleasant children’ points of interest just like the carousel.

What’s the Martha’s Winery City with the gingerbread homes?

Oak Bluffs is the city with the gingerbread homes, and the island takes nice delight in these architectural gems.

What are the very best Martha’s Winery cities with a number of issues to do?

If you wish to have a number of issues to do close by, I like to recommend staying in Oak Bluffs, Edgartown, or Vineyard Haven. These are probably the most hopping cities.

What are the quieter Martha’s Winery cities for a calming getaway?

Chilmark, Aquinnah, and West Tisbury are quiet, rural spots that are perfect for a spot to recharge. Maybe most quiet is Chappaquiddick Island, with no shops on-island.

A row of four colorful gingerbread houses in a wooded area in Martha's Vineyard.
Oak Bluffs’s most well-known image is its Victorian houses.

Oak Bluffs

The down-island city of Oak Bluffs is one among Martha’s Winery’s most well-known (and most photographed!) spots. Nicely-known for its charming gingerbread cottages, historic websites, and great seashore roads, this city gives enjoyable points of interest for guests of all ages.

A number of Steamship Authority ferries from Woods Gap dock right here in Oak Bluffs, in addition to the passenger-only ferry with direct service from Hyannis. Undoubtedly take trip to go to the long-lasting gingerbread homes, a necessary cease for each customer! These charming cottages painted in vibrant hues make a powerful sight that by no means fails to thrill.

Circuit Avenue is the principle road, filled with pleasant spots to buy and eat. Ocean Park gives an inviting seven acres of inexperienced area the place guests can stroll, play Frisbee or take pleasure in a picnic lunch. Plus, stay music and fireworks happen right here each August! 

Inkwell Seaside is a small however common seashore, with turquoise waters and an extended historical past of being a haven for Black American residents and vacationers. The light bay-side waves make this a terrific selection for teenagers.

And maybe the very best children’ exercise in Martha’s Winery is right here in Oak Bluffs: the Flying Horses Carousel, one of many longest operating repeatedly working carousels in America! Kids of all ages love driving its horses. And for individuals of all ages, right here you may store in boutiques, take pleasure in bars and coffeeshops, and absorb loads of native island companies.

A stately white home turned into Edgartown Books bookstore, flying a rainbow pride American flag.
Edgartown might be the very best city on Martha’s Winery for procuring.


Situated on Martha’s Winery’s japanese finish, Edgartown boasts a few of the island’s most elegant and historic houses, many relationship again to when whaling was at its peak within the nineteenth century. These homes have been superbly restored, making Edgartown an attractive place for a stroll.

Edgartown gives loads of charming retailers on Primary Road, with all the things from girls’s attire and artwork galleries to sweet shops lining its downtown district. Discover the varied array of eating choices, with eating places akin to The Seafood Shanty, with breathtaking ocean views and a few of the island’s greatest clam chowder, and The Wharf, with an inviting bar and scrumptious basic diner dishes.

Only a 10-minute stroll from the city middle is without doubt one of the most particular lighthouses on the island, Edgartown Lighthouse, also called Harbor Gentle. Inbuilt 1828, it was really as soon as on a man-made island only a quarter-mile off-shore, however a brand new seashore fashioned in 1939, connecting the lighthouse to the mainland.

Beachgoers will recognize Katama Seaside (also called South Seaside), positioned within the Katama space of Edgartown going through the Atlantic. It’s a barrier seashore, with an intensive stretch of white sand that extends for greater than three miles, good for shell fishing or simply strolling with household and mates. Take into account that the sand will get slim at excessive tide.

At close by Katama Bay, Signature Oyster Farms means that you can take a tour of its native oyster farms. You’ll have a chance to stroll on oyster beds and witness how these scrumptious bivalves are harvested earlier than having fun with an idyllic, farm-to-table lunch.

North of city, Joseph Sylvia State Seaside, often called State Seaside to locals, is a wonderful place for swimming. This sandy seashore was used because the setting for the 1975 film Jaws and boasts miles of sandy shoreline for guests to take pleasure in. You may leap off the Jaws Bridge, too!

On prime of having fun with a seashore expertise, guests to Edgartown also needs to discover a few of its historic landmarks, together with Vincent House Museum and Old Whaling Church. Each of those historic museums present fascinating insights into this island’s previous.

Chappaquiddick Island is technically a part of the city of Edgartown and takes only one minute to get to on the tiny Chappy Ferry, which might match just some automobiles. That stated, I believe it’s greatest to discover Chappaquiddick by bike — it’s small and flat, discovering parking is far simpler, and also you gained’t have to attend within the automobile line for the ferry.

On Chappaquiddick you may go to Cape Poge Wildlife Refuge and its eponymous lighthouse; you may as well try East Seaside, go to the Mytoi Japanese Gardens, or benefit from the infinite expanse of sea at Wasque Level (pronounced WAY-squee).

A downtown area with wooden shingled houses and a street sign reading Vineyard Haven Harbor Cultural District.
Winery Haven seems like probably the most native city on Martha’s Winery.

Winery Haven

Winery Haven is the generally used nickname for the city of Tisbury (totally different from the city of West Tisbury, which we’ll point out additional down). Situated on the North Shore of the island, the Steamship Authority ferry stops right here, nevertheless it’s completely price lingering somewhat!

Very similar to Oak Bluffs and Edgartown, Winery Haven has a bustling ambiance with a number of issues to do. Nonetheless, whereas the opposite two cities really feel tremendous tourism-oriented, Winery Haven feels prefer it’s designed for the numerous locals who name this city residence.

Winery Haven can also be the placement of the Nobnocket Boutique Inn, the place I cherished staying throughout my time in Martha’s Winery! (Extra on Nobnocket under.)

Downtown Winery Haven is a beautiful place to wile away the afternoon hours procuring, whose walkable downtown seems to be simply as timeless because it did a long time in the past. You should definitely cease by Waterside Market for lunch to gasoline up beforehand; they served an enormous BLT that knocked my socks off. 

The Black Dog Tavern, an iconic and world-famous Winery institution, has the very best chef-crafted entrees, good for breakfast, lunch, or dinner. Right here in Winery Haven you may as well go to The Black Dog Store, and Black Dog Bakery (which has nice cookies).

Whether or not or not you’re a historical past buff, the Martha’s Vineyard Museum offers you invaluable perception into the island. (It’s additionally a terrific wet day exercise on the Winery.) Uncover the wealthy historical past and vibrant heritage of Martha’s Winery and its environment on this museum, positioned in an 1890 Victorian marine hospital. Displays function lighthouses in addition to these devoted to the Indigenous Wampanoag individuals.

Lighthouse completionists can cease by the West Chop Lighthouse — whereas this one is just not open to the general public, it does function a beautiful picture opp! It’s a few 30-minute stroll from.

When you’ve got time, do attempt to see a manufacturing at Martha’s Vineyard Playhouse. Situated on Church Road, they placed on a pleasant number of occasions all year long.

Learn Extra: A Customer’s Information to Winery Haven, Martha’s Winery

A row of mailboxes on a rural road in Martha's Vineyard.
West Tisbury is a rural, quiet city in Martha’s Winery.

West Tisbury

West Tisbury, one of many up-island cities on Martha’s Winery, is an idyllic and tranquil village. Comprised of acres of State Forest, serene seashores, and ample farmland, its New England village attraction is preserved by way of basic shops, white church buildings, publish workplaces, and family-run farms.

The relaxed and comfortable vibe makes it really feel like a rustic city and is residence to an intensive vary of regionally produced items. Recent produce, do-it-yourself soaps and lotions, handcrafted wooden furnishings in addition to some nice eating places can all be had. Refuel at Woods Restaurant at Lambert’s Cove, which serves island-inspired meals. 

Purchasing at Alley’s General Store is a should. As one of many oldest repeatedly working retailers on Martha’s Winery, you could find it behind a historic barn with a grey shingled roof. Since 1897, this stoop-to-porch institution sells all the things you might have considered trying throughout your go to.

This rural agricultural neighborhood gives quite a few points of interest which might be each free and cheap. One such attraction is Long Point Wildlife Refuge, an previous prairie remnant now residence to globally uncommon crops and wildlife; additionally that includes sandy seashores, coastal ponds, and small lakes good for hen watching.

Polly Hill Arboretum gives an attractive place for picnicking on Martha’s Winery, that includes a chic oak tree in addition to different species planted to resemble its pure surroundings. This was one of many quietest and most serene locations I visited on the island.

Lastly, Lengthy Cove Pond gives a few of the island’s most breathtaking landscapes, whereas additionally serving as a superb location for snorkeling and fishing.

A clapboard fishing cabin light up in bright golden light at sunset.
The fishing village of Menemsha is a part of Chilmark city on Martha’s Winery.


The south shore city of Chilmark gives each magnificence and tranquility harmoniously. There may be a lot to do and see with its fellow up-island neighbors of West Tisbury and Aquinnah.

One factor I like about Martha’s Winery is visiting native farmstands for regionally made produce. The most effective is The Grey Barn and Farm in Chilmark, which makes glorious cheeses and likewise has loads of contemporary produce, a bakery, and a butcher store. Want a pick-me-up? Chilmark Coffee Roaster is a well-liked spot for each locals and guests. 

Whereas mountaineering and admiring nature’s splendor are rewarding experiences, kayaking or crusing at Nashaquitsa and Stonewall Ponds is one other unbelievable choice.

Many island guests flock to look at the sundown at Menemsha Seaside at Menemsha Village — its waters turn into painted in hues that rival a few of New England’s most gorgeous and romantic sunsets! Surrounded by massive rocks, this seashore gives stunning and peaceable environment. Hire a motorcycle, or simply come down with some seashore chairs to affix everybody else because the solar dips down.

Menemsha Hills Nature Reserve ought to be included on any itinerary to the island. Simply exterior Chilmark, this protected 211-acre reserve boasts various mini-environments akin to woodland groves, coastal plains, and low wetlands, in addition to breathtaking views of Winery Sound and Elizabeth Islands from 308-foot Prospect Hill!

Giant seaside cliffs lit up at sunset in shades of yellow, red, and orange.
The Aquinnah Cliffs are a must-see within the city of Aquinnah.


Aquinnah is the westernmost city on the island, and was previously often called Homosexual Head. It’s the cultural residence of the Aquinnah Wampanoag nation and options a lot pure magnificence, together with gorgeous over-water sunsets at Moshup Seaside (my private favourite seashore on Martha’s Winery!).

If you happen to’re on the lookout for issues to do in Aquinnah, most individuals come to go to the Aquinnah Cliffs, a protected, multi-color pure surprise. Each the cliffs and the seashore are off-limits attributable to their delicate nature, however you may view them from the Aquinnah Cliffs Overlook. I like to recommend visiting at golden hour, simply earlier than sundown, after they gentle up in shiny colours (this was when the picture above was taken).

A go to to the Aquinnah Cultural Center is a should — and gives a beautiful historical past of the Indigenous peoples of Martha’s Winery. This museum is price a go to and strolling distance from the cliffs lookout and Moshup Seaside.

In search of an unbelievable view over the Atlantic Ocean? Climb to the highest of Homosexual Head Gentle, one of many Martha’s Vineyard lighthouses you may go to.

Long Point Wildlife Refuge is an idyllic pure space, which as soon as fashioned a part of an island prairie ecosystem, now boasts a unprecedented assortment of crops and animals — plus a number of seashores and a two-mile mountaineering path in your enjoyment.

A large Martha's Vineyard mansion at the end of a driveway.

The place to Keep on Martha’s Winery

For a quintessential Martha’s Winery keep, Nobnocket Boutique Inn will handle you. I completely cherished my keep right here.

Situated on a quiet road in Winery Haven, homeowners Simon and Annabelle Hunton present excellent service from the second you step into the property. Stylish, fashionable furnishings accentuated with elegant paintings make you’re feeling like pampered royalty with out the pomp and circumstance. 

The visitor rooms exude a quiet magnificence with consolation firmly in thoughts. The Nobnocket achieves that delicate steadiness of a contemporary, fashionable aesthetic whereas preserving the ambiance cozy. Considerate design touches will be discovered all through, from the plush mattress linens to the inviting wainscoting within the bogs. 

Most boutique inns provide complimentary espresso, tea, and even board video games within the foyer, however the Nobnocket ups the ante by providing a little bit of port, whiskey, or brandy, together with gentle snacks, simply in case you fancy a night nightcap. Once you need to stretch your legs, an expansive yard gives the best spot to chill out, dine exterior, or stroll the gorgeous grounds.  

However the Inn’s breakfast is the wow issue right here! Each morning is totally different, often starting with a inventive fruit parfait earlier than shifting to the principle occasion. This could embody waffles with a tasty topping akin to mango and sherbet, avocado toast with egg and pancetta, or creamy bread pudding topped with contemporary berries. All are paired with Chilmark Espresso’s regionally roasted beans, tea, and juice. 

There’s even a turndown service with cookies! No higher option to drift off to dreamland.

Extra on Martha’s Winery and Cape Cod:

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Have you ever been to Martha’s Winery? The place’s your favourite city? Share away!