Which of the 6 Martha’s Winery Cities is Greatest 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 get pleasure from drives on nation roads. Its 87 sq. miles is an oasis of old-world appeal and pure magnificence in equal measure, with each a summer season season and year-round inhabitants.

Situated about 4 miles off the southeast coast of Cape Cod, Massachusetts, quaint cities and contemporary ocean breezes deliver hordes of holiday makers 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 properties.

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. House year-round fishermen and farmers, creatives and entrepreneurs, tradesmen and academics — and a LOT of attorneys and surgeons in the summertime — a robust sense of group and distinctive character is the draw for a lot of to make a house right here. 

Martha’s Winery is a superb place to partake within the easy pleasures of strolling, biking, fishing, boating, crabbing, beachcombing, grilling, or just studying a guide 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 fans (and my husband particularly). However concern not, there’s loads of wine to drink, and a whole lot 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.

Greatest Cities on Martha’s Winery

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

Each single city on Martha’s Winery may be very family-friendly, however Oak Bluffs has some pleasant youngsters’ sights 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 pleasure in these architectural gems.

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

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

What are the quieter Martha’s Winery cities for a soothing 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 properties.

Oak Bluffs

The down-island city of Oak Bluffs is one in all Martha’s Winery’s most well-known (and most photographed!) spots. Effectively-known for its charming gingerbread cottages, historic websites, and great seaside roads, this city provides enjoyable sights 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 outing to go to the enduring gingerbread homes, a vital cease for each customer! These charming cottages painted in vibrant hues make a formidable sight that by no means fails to please.

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

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

And maybe the very best youngsters’ exercise in Martha’s Winery is right here in Oak Bluffs: the Flying Horses Carousel, one of many longest working constantly working carousels in America! Kids of all ages love driving its horses. And for folks of all ages, right here you’ll be able to store in boutiques, get pleasure from 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 buying.


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

Edgartown provides loads of charming outlets on Primary Road, with the whole lot from ladies’s attire and artwork galleries to sweet shops lining its downtown district. Discover the varied array of eating choices, with eating places equivalent 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 heart is likely one of the most particular lighthouses on the island, Edgartown Lighthouse, also referred to as Harbor Mild. In-built 1828, it was really as soon as on a man-made island only a quarter-mile off-shore, however a brand new seaside shaped in 1939, connecting the lighthouse to the mainland.

Beachgoers will recognize Katama Seaside (also referred to as South Seaside), positioned within the Katama space of Edgartown going through the Atlantic. It’s a barrier seaside, with an intensive stretch of white sand that extends for greater than three miles, excellent for shell fishing or simply strolling with household and associates. Remember that the sand will get slender at excessive tide.

At close by Katama Bay, Signature Oyster Farms lets you 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 superb place for swimming. This sandy seaside was used because the setting for the 1975 film Jaws and boasts miles of sandy shoreline for guests to get pleasure from. You’ll be able to bounce off the Jaws Bridge, too!

On prime of having fun with a seaside expertise, guests to Edgartown must also 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 may match just some vehicles. That mentioned, I feel it’s greatest to discover Chappaquiddick by bike — it’s small and flat, discovering parking is far simpler, and also you received’t have to attend within the automobile line for the ferry.

On Chappaquiddick you’ll be able to go to Cape Poge Wildlife Refuge and its eponymous lighthouse; you can too try East Seaside, go to the Mytoi Japanese Gardens, or benefit from the countless 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 looks like essentially the most native city on Martha’s Winery.

Winery Haven

Winery Haven is the generally used nickname for the city of Tisbury (completely 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, but it surely’s completely price lingering somewhat!

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

Winery Haven can be the situation of the Nobnocket Boutique Inn, the place I beloved staying throughout my time in Martha’s Winery! (Extra on Nobnocket beneath.)

Downtown Winery Haven is a beautiful place to wile away the afternoon hours buying, whose walkable downtown appears simply as timeless because it did many years in the past. You should definitely cease by Waterside Market for lunch to gas up beforehand; they served a large BLT that knocked my socks off. 

The Black Dog Tavern, an iconic and world-famous Winery institution, has the very best chef-crafted entrees, excellent for breakfast, lunch, or dinner. Right here in Winery Haven you can too 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 an ideal 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. Reveals characteristic lighthouses in addition to these devoted to the Indigenous Wampanoag folks.

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

If in case you have 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 plentiful farmland, its New England village appeal is preserved by means of normal shops, white church buildings, put up workplaces, and family-run farms.

The relaxed and comfortable vibe makes it really feel like a rustic city and is house 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. 

Procuring at Alley’s General Store is a should. As one of many oldest constantly working retailers on Martha’s Winery, you’ll find it behind a historic barn with a grey shingled roof. Since 1897, this stoop-to-porch institution sells the whole lot it’s your decision throughout your go to.

This rural agricultural group provides quite a few sights which can be each free and cheap. One such attraction is Long Point Wildlife Refuge, an outdated prairie remnant now house to globally uncommon crops and wildlife; additionally that includes sandy seashores, coastal ponds, and small lakes excellent for chook watching.

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

Lastly, Lengthy Cove Pond supplies 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 provides each magnificence and tranquility harmoniously. There’s lots 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. Among the best is The Grey Barn and Farm in Chilmark, which makes wonderful cheeses and in addition 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 climbing and admiring nature’s splendor are rewarding experiences, kayaking or crusing at Nashaquitsa and Stonewall Ponds is one other incredible choice.

Many island guests flock to observe 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 seaside provides lovely and peaceable environment. Hire a motorcycle, or simply come down with some seaside 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 equivalent 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 house of the Aquinnah Wampanoag nation and options a lot pure magnificence, together with gorgeous over-water sunsets at Moshup Seaside (my private favourite seaside on Martha’s Winery!).

In case you’re in search of issues to do in Aquinnah, most individuals come to go to the Aquinnah Cliffs, a protected, multi-color pure marvel. Each the cliffs and the seaside are off-limits as a consequence of their delicate nature, however you’ll be able to view them from the Aquinnah Cliffs Overlook. I like to recommend visiting at golden hour, simply earlier than sundown, once they gentle up in vibrant colours (this was when the picture above was taken).

A go to to the Aquinnah Cultural Center is a should — and provides 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 unimaginable view over the Atlantic Ocean? Climb to the highest of Homosexual Head Mild, one of many Martha’s Vineyard lighthouses you’ll be able to go to.

Long Point Wildlife Refuge is an idyllic pure space, which as soon as shaped 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 climbing path on 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 deal with you. I completely beloved my keep right here.

Situated on a quiet road in Winery Haven, house owners 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 protecting 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 supply 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. If you wish to stretch your legs, an expansive yard supplies the perfect 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 completely different, often starting with a inventive fruit parfait earlier than shifting to the principle occasion. This may embody waffles with a tasty topping equivalent 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!