Adventurous Kate incorporates affiliate hyperlinks. Should you make a purchase order by means of these hyperlinks, I’ll earn a fee at no further price to you. Thanks!
Unspoiled seaside settings, rolling hills, and a relaxed tempo have lengthy attracted guests to the shores of Martha’s Winery. That is, in spite of everything, 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 allure and pure magnificence in equal measure, with each a summer time season and year-round inhabitants.
Positioned about 4 miles off the southeast coast of Cape Cod, Massachusetts, quaint cities and recent 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 most important 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 legal professionals 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 below a tree.
And right here’s one thing to know: regardless of its title, Martha’s Winery doesn’t really comprise any vineyards, a lot to the chagrin of wine lovers (and my husband specifically). However concern not, there’s loads of wine to drink, and a whole bunch of different issues to do in these six fantastic Martha’s Winery cities.

Finest Cities on Martha’s Winery
Each single city on Martha’s Winery could be very family-friendly, however Oak Bluffs has some pleasant youngsters’ points of interest just like the carousel.
Oak Bluffs is the city with the gingerbread homes, and the island takes nice pleasure in these architectural gems.
If you wish to have a number of issues to do close by, I like to recommend staying in Oak Bluffs, Edgartown, or Winery Haven. These are probably the most hopping cities.
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.

Oak Bluffs
The down-island city of Oak Bluffs is one in every of Martha’s Winery’s most well-known (and most photographed!) spots. Effectively-known for its charming gingerbread cottages, historic websites, and fantastic seashore roads, this city presents 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. You may view the ferry schedule right here.
Undoubtedly take day trip to go to the long-lasting gingerbread homes, a necessary cease for each customer! These charming cottages painted in vibrant hues make a formidable sight that by no means fails to thrill.
Circuit Avenue is the principle road, filled with pleasant spots to buy and eat. Ocean Park presents an inviting seven acres of inexperienced area the place guests can stroll, play Frisbee or get pleasure from a picnic lunch. Plus, dwell music and fireworks happen right here each August!
Inkwell Seashore is a small however fashionable seashore, with turquoise waters and a protracted 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 perfect 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 take in loads of native island companies.

Edgartown
Positioned on Martha’s Winery’s japanese finish, Edgartown boasts a few of the island’s most elegant and historic houses, many courting again to when whaling was at its peak within the nineteenth century. These homes have been fantastically restored, making Edgartown a stupendous place for a stroll.
Edgartown presents loads of charming retailers on Principal Road, with every thing from girls’s attire and artwork galleries to sweet shops lining its downtown district. Discover the various array of eating choices, with eating places resembling 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 traditional 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 referred to as Harbor Gentle. In-built 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 respect Katama Seashore (also referred to as South Seashore), positioned within the Katama space of Edgartown dealing with the Atlantic. It’s a barrier seashore, with an in depth stretch of white sand that extends for greater than three miles, good for shell fishing or simply strolling with household and buddies. Needless to say 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 Seashore, often known as State Seashore 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 get pleasure from. You may bounce off the Jaws Bridge, too!
On prime of having fun with a seashore expertise, guests to Edgartown must also discover a few of its historic landmarks, together with Vincent Home Museum and Outdated 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 way simpler, and also you received’t have to attend within the automotive line for the ferry.
On Chappaquiddick you’ll be able to go to Cape Poge Wildlife Refuge and its eponymous lighthouse; you may as well take a look at East Seashore, go to the Mytoi Japanese Gardens, or benefit from the infinite expanse of sea at Wasque Level (pronounced WAY-squee).

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). Positioned on the North Shore of the island, the Steamship Authority ferry stops right here, however it’s completely price lingering a bit of!
Very like Oak Bluffs and Edgartown, Winery Haven has a bustling environment 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 house.
Winery Haven can be the placement of the Nobnocket Boutique Inn, the place I cherished staying throughout my time in Martha’s Winery! (Extra on Nobnocket beneath.)
Downtown Winery Haven is a stunning place to wile away the afternoon hours procuring, whose walkable downtown appears to be like simply as timeless because it did a long time in the past. Make sure you cease by Waterside Marketplace for lunch to gas up beforehand; they served a large BLT that knocked my socks off.
The Black Canine Tavern, an iconic and world-famous Winery institution, has the perfect chef-crafted entrees, good for breakfast, lunch, or dinner. Right here in Winery Haven you may as well go to The Black Canine Retailer, and Black Canine Bakery (which has nice cookies).
Whether or not or not you’re a historical past buff, the Martha’s Winery Museum gives 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. 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 is just not open to the general public, it does function an exquisite picture opp! It’s a few 30-minute stroll from.
In case you have time, do attempt to see a manufacturing at Martha’s Winery Playhouse. Positioned 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

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 allure is preserved by means of basic shops, white church buildings, put up workplaces, and family-run farms.
The relaxed and comfy vibe makes it really feel like a rustic city and is house to an intensive vary of regionally produced items. Recent produce, selfmade 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 Common Retailer is a should. As one of many oldest constantly working retailers on Martha’s Winery, you will discover it behind a historic barn with a grey shingled roof. Since 1897, this stoop-to-porch institution sells every thing you might have considered trying throughout your go to.
This rural agricultural neighborhood presents quite a few points of interest which can be each free and cheap. One such attraction is Lengthy Level Wildlife Refuge, an previous prairie remnant now house to globally uncommon vegetation and wildlife; additionally that includes sandy seashores, coastal ponds, and small lakes good for chicken watching.
Polly Hill Arboretum supplies a stupendous place for picnicking on Martha’s Winery, that includes a sublime 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 supplies a few of the island’s most breathtaking landscapes, whereas additionally serving as a wonderful location for snorkeling and fishing.

Chilmark
The south shore city of Chilmark presents each magnificence and tranquility harmoniously. There may be 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 finest is The Gray Barn and Farm in Chilmark, which makes wonderful cheeses and in addition has loads of recent produce, a bakery, and a butcher store. Want a pick-me-up? Chilmark Espresso 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 improbable possibility.
Many island guests flock to look at the sundown at Menemsha Seashore at Menemsha Village — its waters grow to be painted in hues that rival a few of New England’s most gorgeous and romantic sunsets! Surrounded by massive rocks, this seashore presents stunning and peaceable environment. Hire a motorcycle, or simply come down with some seashore chairs to hitch 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 resembling woodland groves, coastal plains, and low wetlands, in addition to breathtaking views of Winery Sound and Elizabeth Islands from 308-foot Prospect Hill!

Aquinnah
Aquinnah is the westernmost city on the island, and was previously often known as 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 Seashore (my private favourite seashore on Martha’s Winery!).
Should you’re searching for 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 seashore are off-limits attributable to 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, after they gentle up in brilliant colours (this was when the picture above was taken).
A go to to the Aquinnah Cultural Heart is a should — and presents an exquisite 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 Seashore.
In search of an unbelievable view over the Atlantic Ocean? Climb to the highest of Homosexual Head Gentle, one of many Martha’s Winery lighthouses you’ll be able to go to.
Lengthy Level 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 vegetation and animals — plus a number of seashores and a two-mile climbing path on your enjoyment.

The place to Keep on Martha’s Winery
For a quintessential Martha’s Winery keep, Nobnocket Boutique Inn will care for you. I completely cherished my keep right here.
Positioned on a quiet road in Winery Haven, homeowners Simon and Annabelle Hunton present excellent service from the second you step into the property. Stylish, trendy furnishings accentuated with elegant paintings make you are 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 stability of a contemporary, fashionable aesthetic whereas holding the environment cozy. Considerate design touches could 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 wish to stretch your legs, an expansive yard supplies the best spot to calm down, 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 transferring to the principle occasion. This could embody waffles with a tasty topping resembling mango and sherbet, avocado toast with egg and pancetta, or creamy bread pudding topped with recent 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:
Extra on Massachusetts:
Better of Boston:
Have you ever been to Martha’s Winery? The place’s your favourite city? Share away!
Get e mail updates from KateBy no means miss a put up. Unsubscribe anytime!