18 Enjoyable Issues to do in Oak Bluffs MA


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Oak Bluffs is what involves thoughts when most individuals consider Martha’s Winery! This lovely city is probably essentially the most well-known place in Martha’s Winery, dwelling to the world-famous Victorian structure, a historic carousel, and exquisite seashores.

I completely cherished Oak Bluffs and I believe that if you wish to be primarily based in a city in your journey to Martha’s Winery, Oak Bluffs is a incredible selection.

Oak Bluffs is among the three main cities within the extra populated “down-island” a part of Martha’s Winery (the opposite two are Winery Haven and Edgartown). The city is thought for its vibrant and welcoming environment, beautiful 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.

Immediately, Oak Bluffs is arguably the preferred vacation spot on Martha’s Winery, due to 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 also be dwelling to a various inhabitants, with folks from all walks of life coming collectively to benefit from the island way of life.

One other factor that makes Oak Bluffs shine is a number of beautiful seashores, akin to Inkwell Seaside and Joseph Sylvia State Seaside. Then there are the colourful gingerbread cottages, that are a sort of Victorian structure that’s distinctive to Martha’s Winery.

The city can also be dwelling to the Flying Horses Carousel, which is a Nationwide Historic Landmark and is among the oldest working carousels in the US.

Let’s check out the perfect issues to do in Oak Bluffs MA! You’re going to like it right here.

(Planning a visit to Martha’s Winery? You’ll want to try my information to the cities of Martha’s Winery, in addition to profiles on the cities of Edgartown and Winery Haven!)

This put up was revealed in October 2023.

Several boutiques in a row on a quiet street in downtown Oak Bluffs.

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 outlets, eating places, and artwork galleries. You may simply spend a few full afternoons shopping the small companies!

If you wish to be taught extra about Oak Bluffs, how about making an attempt an audio tour by yourself? This audio tour offers guests the background on the standard 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 concerning 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 motorcycle right here in the course of your go to. There are a selection of motorbike leases round city, many conveniently situated proper by the ferry, together with All Star Bike Leases, Anderson’s Bike Leases, and Pedego Martha’s Winery, simply to call just a few!

Most bike outlets hire common bikes, whereas Pedego additionally has eBikes — which I like to recommend renting for those who plan to bike up-island as far-off as Chilmark or Aquinnah. The motor will enable you to recover from these huge hills!

A row of four colorful gingerbread houses in a wooded area in Martha's Vineyard.
Don’t you need to transfer into one in all these homes?

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 had been a part of the Methodist campground based within the Nineteenth century. These architectural marvels are identified 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.

Immediately, the Gingerbread Homes are privately owned by particular person homeowners — nonetheless, most of the houses are open to the general public for excursions throughout the summer time months. Guests can be taught concerning the historical past of the houses and see how they’re adorned inside. 

I discovered it surprisingly troublesome to get good pictures of the Gingerbread Homes on a sunny day as a result of they’re surrounded by bushes and there have been so many patches of daylight and shadow. You may get higher pictures on a cloudy day!

And naturally, understand that most of those homes are folks’s houses. Be happy to take pictures, however preserve a respectful distance and don’t sit on their porches or poke your head in any home windows.

People riding an old-fashioned carousel in Martha's Vineyard.
Flying Horses Carousel, by way of Michael Gordon on Shutterstock

Flying Horses Carousel

Get again in contact together with your internal baby on one of many oldest working carousels in the US, proper right here in Oak Bluffs! In-built 1876, The Flying Horses Carousel is among 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.

Positioned within the coronary heart of Oak Bluffs, the carousel is open from April to October, and tickets could be bought on the ticket sales space (although know that hours are shorter outdoors the height summer time months).

An empty sandy beach in Martha's Vineyard, an empty lifeguard's stand looking over the water.

Go to Inkwell Seaside and Joseph Sylvia State Seaside

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 Seaside and Joseph Sylvia State Seaside.

Inkwell Seaside is among the primary seashores on the town, near the ferry and downtown Oak Bluffs. You’ll discover gentle sand and distance views of Cape Cod right here. Traditionally, Inkwell Seaside was the seaside for the Black group, and is a part of the African-American Heritage Path at present.

Additional down the highway close to the Jaws Bridge, Joseph Sylvia State Seaside 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 Seaside gives quite a lot of facilities, together with a bathhouse, a playground, and a picnic space. The seaside can also be a well-liked spot for swimming, sunbathing, and fishing.

A row of elegant Victorian houses with well-manicured rhododendron bushes in Martha's Vineyard.

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 Path options 15 websites, together with church buildings, colleges, and houses, and gives a glimpse into the lives of among the most influential African-People who’ve known 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 outstanding Black household. The cottage is now a museum that tells the story of the Shearer household and their contributions to the island. Guests can be taught concerning the household’s position within the abolitionist motion, their work as educators, and their love of the humanities.

One other necessary 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 a good looking instance of Gothic Revival structure, and it has been a gathering place for the Black group on Martha’s Winery for over a century. Immediately, the chapel hosts quite a lot of occasions, together with live shows, lectures, and non secular providers.

Go to the Mariposa Museum

There’s a lot to see on the Mariposa Museum! With over 5,000 sq. toes of exhibit area, there’s something for everybody. When you love artwork, be sure that to cease by the rotating artwork gallery. When you like historical past, you’ll benefit from the displays concerning the historical past of Oak Bluffs and Martha’s Winery. The museum additionally has displays concerning the historical past of the Wampanoag tribe. And if in case you have children, they are going to love the hands-on displays. 

The museum is devoted to preserving the historical past and tradition of Oak Bluffs and the encircling space with quite a lot of displays, together with a duplicate of a Nineteenth-century cottage, a group 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 gives quite a lot of occasions and applications. There are lectures, live shows, and workshops, in addition to a present store the place you should purchase souvenirs. Admission is $10 for adults and free for youngsters below 5.

Two people sitting on a park bench in Martha's Vineyard, on the edge of the water.

Go on a Scavenger Hunt

What higher option to get to know Oak Bluffs in a really enjoyable means than to participate in a scavenger hunt! You obtain the scavenger hunt to your cellphone and may discover by yourself or with a journey companion at your personal tempo, fixing clues concerning the Winery.

This interactive hunt could have you roaming completely different areas as you uncover Oak Bluffs’s wealthy tradition, epic landmarks, and extra, all whereas fixing puzzles utilizing your cellphone! One other nice characteristic of this scavenger hunt is that you simply get to speak with the locals as you discover. 

Put on snug footwear, be sure that your cellphone is charged, and prepare to have some critical enjoyable.

Kayaks lying on the beach on the edge of a pond in Martha's Vineyard.
Martha’s Winery is a superb place to kayak! Through Shutterstock.

Go Paddleboarding or Kayaking at Dawn

Oak Bluffs is a good looking place to go paddleboarding or kayaking. The calm waters of the Oak Bluffs harbor are excellent for inexperienced persons, whereas the extra skilled paddlers can discover the encircling coves and inlets. You may discover by yourself or with a information.

Water sports activities are vastly well-liked on Martha’s Winery, and Oak Bluffs isn’t any exception. Paddleboarding is a incredible means to look at the solar rise on the island. Think about a peaceable journey with heat colours lighting up the early morning sky with mild wind and glassy water surrounding you in your paddleboard or kayak. 

Meet your information simply earlier than dawn, the place you might 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 an everyday incidence. It’ll 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 gear, whether or not you select to paddleboard or kayak. 

A low cement bridge hanging over a channel of bright blue water in Martha's Vineyard.
The Jaws Bridge, between Oak Bluffs and Edgartown, by way of Shutterstock.

Jaws Bridge

Are you a Jaws fan? You’ve come to the suitable island. Jaws Bridge is a historic landmark that connects Oak Bluffs to the city of Edgartown. The bridge was in-built 1932 and is lovingly named after the 1975 film Jaws, which was filmed on Martha’s Winery. 

It’s a well-liked vacationer vacation spot, as the world is thought not just for the long-lasting film however for its lovely seashores and surroundings. The bridge can also be a well-liked spot for fishing and swimming, even supposing it has been identified to be frequented by sharks.

As it’s a drawbridge, chances are you’ll run into stalled visitors when it’s raised throughout peak summer time hours to permit boat visitors to go beneath. There are additionally pedestrian walkways on the bridge, which supply beautiful views of the encircling space.

Seize a Drink at Mocha Mott’s

As a well-liked espresso store situated in Oak Bluffs, Mocha Mott’s is thought for its scrumptious espresso and baked items – and only a excellent spot to seize a fast chunk or loosen up with pals. The store is situated within the coronary heart of Oak Bluffs, only a brief stroll from the seaside. The environment at Mocha Mott’s is inviting, the place the partitions are adorned with native art work, and the workers is pleasant. 

You’re certain to listen to some good jazz or different fashionable music enjoying 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 also be identified for its dedication to the group. The store recurrently sponsors occasions akin to open mic nights and artwork reveals, that are an effective way to get to know year-round Winery residents.

A big white lighthouse next to an old-fashioned metal sign reading "Telegraph Hill."
East Chop Mild is well worth the journey. Through Shutterstock.

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 situated on the northernmost level of Oak Bluffs, with views of Cape Cod within the distance.

The East Chop Lighthouse was in-built 1838 and is among 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; you should definitely verify their web site for up to date hours. Admission is $5 for adults and kids below 12 are free.

A big green park with a Victorian wooden gazebo and lots of Canadian geese on the grass.
Benefit from the park, however be careful for the geese!

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 variety of Canadian geese). With seven acres of grassy area, it’s a well-liked spot for each locals and vacationers to loosen up and benefit from the outside.

Whereas the geese can generally be a little bit of a difficulty, it is a actually beautiful inexperienced area, and makes a pleasant spot for a picnic in Oak Bluffs. I additionally cherished this park for images choices.

See a Martha’s Winery Sharks Baseball Sport

The Martha’s Winery 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, situated on the Martha’s Winery Regional Excessive Faculty campus, which is additional inland in Oak Bluffs on the sting of the state forest.

The Sharks had been based in 2011 by a bunch of native businessmen who needed to supply a summer time baseball expertise for faculty gamers. The staff’s first head coach was former Boston Crimson 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 Crimson Sox! Plenty of children on Martha’s Winery develop up dreaming of enjoying for the Sharks someday.

Catch a Film at Strand Theater

Oak Bluffs’ historic movie show, The Strand, was in-built 1914 and has been a beloved a part of the group ever since. The theater reveals first-run films, in addition to basic movies, live shows, and performs. The theater can also 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 displaying films ever since. The theater was renovated within the Nineties, and it’s now a state-of-the-art facility.

With a big display screen and cozy seating, the sound system is great, and the popcorn is contemporary and scrumptious. Simply know that if it occurs to be a wet day on the Winery, it will possibly 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. Positioned on Circuit Avenue, only a brief stroll from the ferry terminal, it’s the proper place to seize a candy deal with earlier than a day of exploring the island. Black Door gives a singular spin on basic donuts with connoisseur flavors made contemporary day by day. 

The store is thought for its artistic taste combos, akin to Strawberry Hibiscus and Chocolate Sea Salt, and basic favorites like Boston Cream and Vanilla Bean. With new flavors launched recurrently, there’s all the time one thing new to attempt.

Get able to line up in your donuts, together with what looks like half of Oak Bluffs — however the line strikes shortly.

Often open till midnight, Black Door Donuts is the proper spot for a late-night deal with. The store has a heat and alluring environment and the menu is displayed on handwritten chalkboard. The workers is pleasant and welcoming and will probably be more than pleased that can assist 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 vigorous environment with a big deck that gives beautiful views of the water, and the inside is adorned in a basic New England model.

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 great and the service is impeccable.

Along with its scrumptious meals, Lookout Tavern is thought for its in depth beer checklist. With over 20 beers on faucet and a rigorously curated choice of native and regional craft brews, the educated workers is all the time joyful to make suggestions and enable you to discover the proper beer to enhance your meal.

Have an Ice Cream at Mad Martha’s

Mad Martha’s Ice Cream Store 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 gives all kinds of flavors to select from, together with basic 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 truffles.

The store is situated in an enthralling outdated constructing with a comfortable, welcoming inside. The partitions are adorned with colourful work and decorations, and the workers 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 gives beautiful views of Nantucket Sound and the encircling countryside. The course is difficult however truthful, with extensive fairways and huge greens. The workers is pleasant and welcoming, and the clubhouse gives quite a lot of facilities, together with a professional store, restaurant, and bar.

This historic course is a favourite amongst golfers of all talent ranges. The course winds its means via rolling hills, mature bushes, 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 beautiful views it gives. Actually, I’m not a golfer and may’t communicate to what makes golf nice — however individuals who golf actually love this course.

The view across the bay in Oak Bluffs, Martha's Vineyard, several waterfront homes in the distance.

Finest 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 a good looking and seaside time to go to, however you could 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 almost universally higher (and dryer!) than late spring, and I might suggest moving 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, nevertheless it was heat and sunny throughout the day. Seashores had been practically abandoned — I couldn’t imagine how a lot the island had emptied out. It is a huge distinction from Europe, the place September continues to be one of many huge trip months.

Spring and fall will also be beautiful instances to go to Martha’s Winery, although understand that some companies have a tendency to shut from late fall via early spring.

Winter is a really quiet time in Oak Bluffs, although there are many locals who dwell right here year-round. You need to know that most of the gingerbread cottages in Oak Bluffs do not need an sufficient heating system, which makes them very powerful to dwell in throughout the winter months. You need to ask the precise householders for extra data — or, higher but, keep in a resort as an alternative.

A small speedboat named the Little Dipper docked in the water in Martha's Vineyard.

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 automotive 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 regularly.

However one of the simplest ways to get round Martha’s Winery is by bicycle. You may hire from a number of outlets on the town — All Star Bike Leases, Anderson’s Bike Leases, and Pedego Martha’s Winery are all good choices. Pedego has eBikes, that are an incredible selection 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.)

An elaborate slate blue Victorian house with a white picket fence and lots of white wooden cutouts as decoration.

Is Oak Bluffs Price It?

Oak Bluffs is totally pleasant! You’ll love this city and take 1,000,000 pictures of it. I can see how Oak Bluffs simply will get below folks’s pores and skin and brings them again to the Winery for years to return.

I hope you take pleasure in Oak Bluffs as a lot as I did!

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