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Oak Bluffs is what involves thoughts when most individuals consider Martha’s Winery! This lovely city is probably probably the most well-known place in Martha’s Winery, dwelling to the world-famous Victorian structure, a historic carousel, and exquisite seashores.
I completely beloved Oak Bluffs and I feel that if you wish to be based mostly in a city in your journey to Martha’s Winery, Oak Bluffs is a unbelievable alternative.
Oak Bluffs is without doubt one of the three main cities within the extra populated “down-island” a part of Martha’s Winery (the opposite two are Vineyard Haven and Edgartown). The city is understood for its vibrant and welcoming ambiance, gorgeous views, and welcoming residents.
The city has a wealthy historical past, courting again to the 1800s when it was a well-liked summer time vacation spot for Methodist camp conferences, and later for rich Black People.
At present, Oak Bluffs is arguably the preferred vacation spot on Martha’s Winery, because of the city’s many distinctive qualities and its relaxed and pleasant vibe. Guests are sometimes greeted with a smile and a wave. The city can be dwelling to a various inhabitants, with folks from all walks of life coming collectively to benefit from the island life-style.
One other factor that makes Oak Bluffs shine is a number of gorgeous seashores, reminiscent of Inkwell Seashore and Joseph Sylvia State Seashore. Then there are the colourful gingerbread cottages, that are a kind of Victorian structure that’s distinctive to Martha’s Winery.
The city can be dwelling to the Flying Horses Carousel, which is a Nationwide Historic Landmark and is without doubt one of the oldest working carousels in the US.
Let’s check out the perfect issues to do in Oak Bluffs MA! You’re going to find it irresistible right here.
(Planning a visit to Martha’s Winery? Make sure to take a look at my guide to the towns of Martha’s Vineyard, in addition to profiles on the cities of Edgartown and Vineyard Haven!)
This publish was printed in October 2023.
Issues To Do in Oak Bluffs, Massachusetts
Discover Oak Bluffs on Foot or by Bike
Oak Bluffs is ideal for exploring by yourself. I like to recommend beginning your day with a stroll down Circuit Avenue. That is the primary road in Oak Bluffs, lined with retailers, eating places, and artwork galleries. You’ll be able to simply spend a few full afternoons looking the small companies!
If you wish to study extra about Oak Bluffs, how about making an attempt an audio tour by yourself? This audio tour offers guests the background on the common-or-garden origins of Oak Bluffs and the way it turned the preferred vacation spot on Martha’s Winery. Alongside the way in which, you’ll discover out a lot in regards to the city’s historical past, in addition to the perfect locations to eat and drink.
Martha’s Winery is finest explored on two wheels, so I like to recommend renting a motorbike right here at some stage in your go to. There are a variety of motorbike leases round city, many conveniently positioned proper by the ferry, together with All Star Bike Rentals, Anderson’s Bike Rentals, and Pedego Martha’s Vineyard, simply to call a number of!
Most bike retailers hire common bikes, whereas Pedego additionally has eBikes — which I like to recommend renting for those who plan to bike up-island as distant as Chilmark or Aquinnah. The motor will assist you to recover from these huge hills!
Go to the Well-known Gingerbread Homes
The Gingerbread Homes, a world-famous assortment of colourful Victorian structure, are distinctive to Oak Bluffs. Initially, these homes have been a part of the Methodist campground based within the Nineteenth century. These architectural marvels are recognized for his or her intricate woodwork, vibrant colours, and attention-grabbing designs. They’re a testomony to the creativity and artistry of the folks of Oak Bluffs and add a contact of caprice to this already postcard-perfect city.
At present, the Gingerbread Homes are privately owned by particular person house owners — nevertheless, most of the properties are open to the general public for excursions in the course of the summer time months. Guests can study in regards to the historical past of the properties and see how they’re embellished inside.
I discovered it surprisingly tough to get good pictures of the Gingerbread Homes on a sunny day as a result of they’re surrounded by timber and there have been so many patches of daylight and shadow. You may get higher pictures on a cloudy day!
And naturally, take into account that most of those homes are folks’s properties. Be happy to take pictures, however maintain a respectful distance and don’t sit on their porches or poke your head in any home windows.
Flying Horses Carousel
Get again in contact together with your internal youngster on one of many oldest working carousels in the US, proper right here in Oak Bluffs! Inbuilt 1876, The Flying Horses Carousel is without doubt one of the few carousels within the nation that also has its unique horses, that includes 48 hand-carved picket horses, every of them distinctive.
The carousel additionally has a Wurlitzer organ that performs music because the carousel rotates. It’s a shocking piece of nostalgia that’s on the Register of Historic Locations.
Situated within the coronary heart of Oak Bluffs, the carousel is open from April to October, and tickets might be bought on the ticket sales space (although know that hours are shorter exterior the height summer time months).
Go to Inkwell Seashore and Joseph Sylvia State Seashore
Martha’s Winery is dwelling to many nice seashores, however you don’t have to depart Oak Bluffs to discover a good stretch of sand. Oak Bluffs is dwelling to a number of nice seashores, together with Inkwell Seashore and Joseph Sylvia State Seashore.
Inkwell Seashore is without doubt one of the essential seashores on the town, near the ferry and downtown Oak Bluffs. You’ll discover comfortable sand and distance views of Cape Cod right here. Traditionally, Inkwell Seashore was the seaside for the Black group, and is a part of the African-American Heritage Path at the moment.
Additional down the street close to the Jaws Bridge, Joseph Sylvia State Seashore is a bigger, extra developed seaside. The seaside is called after Joseph Sylvia, an area fisherman who was misplaced at sea in 1927.
Joseph Sylvia State Seashore presents quite a lot of facilities, together with a bathhouse, a playground, and a picnic space. The seaside can be a well-liked spot for swimming, sunbathing, and fishing.
Discover Martha’s Winery African-American Heritage Path
Take a self-guided strolling tour that explores the wealthy historical past and tradition of Black life on the island. The African-American Heritage Trail options 15 websites, together with church buildings, colleges, and houses, and presents a glimpse into the lives of a few of the most influential African-People who’ve referred to as Martha’s Winery dwelling.
One of many highlights of the path is the Shearer Cottage, a historic dwelling that was as soon as owned by a distinguished Black household. The cottage is now a museum that tells the story of the Shearer household and their contributions to the island. Guests can study in regards to the household’s function within the abolitionist motion, their work as educators, and their love of the humanities.
One other vital cease on the path is the Union Chapel, a historic church that was based in 1880 by a number of Black summer time residents. The chapel is an attractive instance of Gothic Revival structure, and it has been a gathering place for the Black group on Martha’s Winery for over a century. At present, the chapel hosts quite a lot of occasions, together with concert events, lectures, and spiritual providers.
Go to the Mariposa Museum
There may be a lot to see on the Mariposa Museum! With over 5,000 sq. ft of exhibit house, there’s something for everybody. In case you love artwork, make sure that to cease by the rotating artwork gallery. In case you like historical past, you’ll benefit from the displays in regards to the historical past of Oak Bluffs and Martha’s Winery. The museum additionally has displays in regards to the historical past of the Wampanoag tribe. And in case you have youngsters, they may love the hands-on displays.
The museum is devoted to preserving the historical past and tradition of Oak Bluffs and the encompassing space with quite a lot of displays, together with a reproduction of a Nineteenth-century cottage, a set of Native American artifacts, and a show of the historical past of the Black group in Oak Bluffs.
Along with the displays, the Mariposa Museum presents quite a lot of occasions and packages. There are lectures, concert events, and workshops, in addition to a present store the place you should purchase souvenirs. Admission is $10 for adults and free for youngsters underneath 5.
Go on a Scavenger Hunt
What higher option to get to know Oak Bluffs in a really enjoyable means than to take part in a scavenger hunt! You obtain the scavenger hunt to your cellphone and may discover by yourself or with a journey companion at your individual tempo, fixing clues in regards to the Winery.
This interactive hunt could have you roaming totally different areas as you uncover Oak Bluffs’s wealthy tradition, epic landmarks, and extra, all whereas fixing puzzles utilizing your cellphone! One other nice function of this scavenger hunt is that you just get to speak with the locals as you discover.
Put on comfy sneakers, make sure that your cellphone is charged, and prepare to have some critical enjoyable.
Go Paddleboarding or Kayaking at Dawn
Oak Bluffs is an attractive place to go paddleboarding or kayaking. The calm waters of the Oak Bluffs harbor are excellent for newcomers, whereas the extra skilled paddlers can discover the encompassing coves and inlets. You’ll be able to discover by yourself or with a information.
Water sports activities are vastly standard on Martha’s Winery, and Oak Bluffs isn’t any exception. Paddleboarding is a fantastic way to look at the solar rise on the island. Think about a peaceable journey with heat colours lighting up the early morning sky with light wind and glassy water surrounding you in your paddleboard or kayak.
Meet your information simply earlier than dawn, the place you could have the choice to seize a espresso to get you going. Then paddle to a protected harbor the place wildlife recognizing and fish spawning are a daily incidence. It can set the stage for a tremendous morning and a calming remainder of your day.
Costs for this expertise begin at USD $75 per individual. This contains espresso and tools, whether or not you select to paddleboard or kayak.
Jaws Bridge
Are you a Jaws fan? You’ve come to the fitting island. Jaws Bridge is a historic landmark that connects Oak Bluffs to the city of Edgartown. The bridge was inbuilt 1932 and is lovingly named after the 1975 film Jaws, which was filmed on Martha’s Winery.
It’s a standard vacationer vacation spot, as the realm is understood not just for the long-lasting film however for its lovely seashores and surroundings. The bridge can be a well-liked spot for fishing and swimming, although it has been recognized to be frequented by sharks.
As it’s a drawbridge, you could run into stalled site visitors when it’s raised throughout peak summer time hours to permit boat site visitors to move beneath. There are additionally pedestrian walkways on the bridge, which provide gorgeous views of the encompassing space.
Seize a Drink at Mocha Mott’s
As a well-liked espresso store positioned in Oak Bluffs, Mocha Mott’s is understood for its scrumptious espresso and baked items – and only a excellent place to seize a fast chew or calm down with mates. The store is positioned within the coronary heart of Oak Bluffs, only a brief stroll from the seaside. The ambiance at Mocha Mott’s is inviting, the place the partitions are adorned with native paintings, and the employees is pleasant.
You’re certain to listen to some good jazz or different fashionable music taking part in within the background. Whether or not you’re in search of a spot to check, work, or simply hang around, Mocha Mott’s is a superb place to be.
Along with its espresso and baked items, Mocha Mott’s can be recognized for its dedication to the group. The store often sponsors occasions reminiscent of open mic nights and artwork exhibits, that are a good way to get to know year-round Winery residents.
Take a Coastal Drive to the East Chop Lighthouse
Martha’s Winery is dwelling to a handful of lighthouses, and the East Chop Mild is the primary lighthouse of Oak Bluffs. The lighthouse is positioned on the northernmost level of Oak Bluffs, with views of Cape Cod within the distance.
The East Chop Lighthouse was inbuilt 1838 and is without doubt one of the oldest lighthouses on Martha’s Winery. When you attain the lighthouse, you possibly can park within the lot and take a brief stroll to the bottom of the tower.
The lighthouse is open to the general public from Memorial Day to Columbus Day; make sure you verify their website for up to date hours. Admission is $5 for adults and youngsters underneath 12 are free.
Chill Out at Ocean Park
Ocean Park is a public park on the town that sits on a hill overlooking the Atlantic Ocean. It’s surrounded by Victorian homes and residential to a pleasant gazebo (together with a whole lot of Canadian geese). With seven acres of grassy house, it’s a standard spot for each locals and vacationers to calm down and benefit from the open air.
Whereas the geese can typically be a little bit of a problem, it is a actually pretty inexperienced house, and makes a pleasant spot for a picnic in Oak Bluffs. I additionally beloved this park for pictures choices.
See a Martha’s Winery Sharks Baseball Recreation
The Martha’s Vineyard Sharks are a collegiate summer time baseball staff that performs within the Futures Collegiate Baseball League. They play dwelling video games at Winery Baseball Park, positioned on the Martha’s Winery Regional Excessive College campus, which is additional inland in Oak Bluffs on the sting of the state forest.
The Sharks have been based in 2011 by a gaggle of native businessmen who wished to supply a summer time baseball expertise for school gamers. The staff’s first head coach was former Boston Purple Sox pitcher Bob Stanley. The Sharks have been very profitable since their inception, profitable the FCBL championship in 2012, 2014, 2015, and 2017.
The Sharks are a well-liked staff on Martha’s Winery, and their video games are sometimes well-attended. It’s additionally good to exit to a recreation that’s simply FUN and doesn’t price an arm and a leg, just like the Purple Sox! Plenty of youngsters on Martha’s Winery develop up dreaming of taking part in for the Sharks sooner or later.
Catch a Film at Strand Theater
Oak Bluffs’ historic movie show, The Strand, was inbuilt 1914 and has been a beloved a part of the group ever since. The theater exhibits first-run motion pictures, in addition to traditional movies, concert events, and performs. The theater can be dwelling to the Martha’s Winery Movie Competition.
The theater has a wealthy historical past. It was initially constructed as a vaudeville theater, and it hosted many well-known performers in its early years. Within the Thirties, the theater was transformed right into a movie show, and it has been exhibiting motion pictures ever since. The theater was renovated within the Nineteen Nineties, and it’s now a state-of-the-art facility.
With a big display screen and comfy seating, the sound system is superb, and the popcorn is contemporary and scrumptious. Simply know that if it occurs to be a wet day on the Winery, it could actually get very busy right here!
Seize a Donut at Black Door Donuts
Black Door Donuts is a must-try for any customer to Oak Bluffs. Situated on Circuit Avenue, only a brief stroll from the ferry terminal, it’s the right place to seize a candy deal with earlier than a day of exploring the island. Black Door presents a novel spin on traditional donuts with connoisseur flavors made contemporary day-after-day.
The store is understood for its artistic taste combos, reminiscent of Strawberry Hibiscus and Chocolate Sea Salt, and traditional favorites like Boston Cream and Vanilla Bean. With new flavors launched often, there’s all the time one thing new to attempt.
Get able to line up in your donuts, together with what appears like half of Oak Bluffs — however the line strikes shortly.
Often open till midnight, Black Door Donuts is the right spot for a late-night deal with. The store has a heat and welcoming ambiance and the menu is displayed on handwritten chalkboard. The employees is pleasant and welcoming and can be very happy that will help you resolve which distinctive donuts to attempt.
Eat Dinner at Lookout Tavern
This neighborhood tavern is nestled within the coronary heart of historic downtown, overlooking the Atlantic Ocean, and only a brief stroll from the ferry terminal. It has a full of life ambiance with a big deck that gives gorgeous views of the water, and the inside is embellished in a traditional New England type.
One of many issues that makes Lookout Tavern stand out is its dedication to contemporary, locally-sourced substances. From mouthwatering lobster rolls and crispy fried oysters to juicy burgers and steaks, there’s one thing for everybody to take pleasure in. Don’t overlook to save lots of room for dessert – the chocolate lava cake is a decadent deal with! Total, the meals is superb and the service is impeccable.
Along with its scrumptious meals, Lookout Tavern is understood for its intensive beer listing. With over 20 beers on faucet and a fastidiously curated choice of native and regional craft brews, the educated employees is all the time completely happy to make suggestions and assist you to discover the right beer to enrich your meal.
Have an Ice Cream at Mad Martha’s
Mad Martha’s Ice Cream Shop is a beloved native establishment, well-known for its scrumptious ice cream and distinctive flavors. Based in 1971, the store has turn into a must-visit vacation spot for vacationers and locals alike.
The menu at Mad Martha’s presents all kinds of flavors to select from, together with traditional favorites like chocolate, vanilla, and strawberry, in addition to extra uncommon creations like Chappy Chocolate Chip and Menemsha Mint. Along with ice cream, Mad Martha’s additionally serves quite a lot of different candy treats, together with sundaes, milkshakes, and ice cream desserts.
The store is positioned in a captivating previous constructing with a comfy, welcoming inside. The partitions are adorned with colourful work and decorations, and the employees is all the time pleasant and useful.
Play a Spherical of Golf at Farm Neck Golf Membership
Problem your self on one of many oldest and most prestigious golf programs on the island. This 9-hole public course presents gorgeous views of Nantucket Sound and the encompassing countryside. The course is difficult however truthful, with large fairways and huge greens. The employees is pleasant and welcoming, and the clubhouse presents quite a lot of facilities, together with a professional store, restaurant, and bar.
This historic course is a favourite amongst golfers of all ability ranges. The course winds its means by rolling hills, mature timber, and coastal wetlands, offering a serene and picturesque setting for a spherical of golf. The fairways are well-manicured and the greens are quick and true.
What makes Farm Neck Golf Membership really particular is its location and the gorgeous views it presents. Truthfully, I’m not a golfer and may’t converse to what makes golf nice — however individuals who golf actually love this course.
Greatest Time to Go to Oak Bluffs, Massachusetts
Martha’s Winery may be very a lot a summer time vacation spot — and that goes for Oak Bluffs in addition to the remainder of the island. In July and August, you’ll have peak summer time temperatures (and peak summer time crowds). It’s an attractive and seaside time to go to, however you is likely to be ready awhile to get into eating places, and features are lengthy.
I like to recommend going a bit low season if attainable. In Massachusetts, early fall is sort of universally higher (and dryer!) than late spring, and I’d advocate entering into September for those who can.
I visited Martha’s Winery in late September and it was past excellent. It wasn’t fairly heat sufficient to swim within the ocean, but it surely was heat and sunny in the course of the day. Seashores have been almost abandoned — I couldn’t imagine how a lot the island had emptied out. This can be a huge distinction from Europe, the place September continues to be one of many huge trip months.
Spring and fall may also be pretty occasions to go to Martha’s Winery, although take into account that some companies have a tendency to shut from late fall by early spring.
Winter is a really quiet time in Oak Bluffs, although there are many locals who stay right here year-round. It’s best to know that most of the gingerbread cottages in Oak Bluffs don’t have an sufficient heating system, which makes them very robust to stay in in the course of the winter months. It’s best to ask the precise householders for extra data — or, higher but, keep in a resort as a substitute.
Getting Round Martha’s Winery from Oak Bluffs
Martha’s Winery is a straightforward place to get round, even for those who didn’t take your automobile over on the ferry! The city of Oak Bluffs is simple to get round on foot, and to get to different locations on the island, there are many bus routes that run frequently.
However the easiest way to get round Martha’s Winery is by bicycle. You’ll be able to hire from a number of retailers on the town — All Star Bike Rentals, Anderson’s Bike Rentals, and Pedego Martha’s Vineyard are all good choices. Pedego has eBikes, that are an amazing alternative for those who plan on biking up-island to Chilmark and Aquinnah, which is an extra distance and hillier journey.
As for attending to Oak Bluffs, the primary Steamship Authority ferries from Woods Gap on the mainland come both into Oak Bluffs or Winery Haven. (These cities are a 10-minute drive aside; it doesn’t actually matter which one you come into, or in case your ferry will get rescheduled to a special departure hub, as mine did.)
Is Oak Bluffs Price It?
Oak Bluffs is totally pleasant! You’ll love this city and take one million pictures of it. I can see how Oak Bluffs simply will get underneath folks’s pores and skin and brings them again to the Winery for years to come back.
I hope you take pleasure in Oak Bluffs as a lot as I did!
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