Ultimate Guide to Oak Bluffs, Martha’s Vineyard

Introduction

Oak Bluffs is the most heavily visited town on Martha’s Vineyard, especially so for day-trippers. Here one can spend the better part of a day enjoying the sights and history of the famous gingerbread cottages, lazing on white-sand beaches, and taking in some world-class seafood and summer specialty drinks on the harbor.

As you approach Oak Bluffs via ferry, the first thing you will notice is a large, open green space. This is Ocean Park. It is a great place from which to launch your exploration, and is always within walking distance of the major attractions in Oak Bluffs. At any point, you can come back here to take off your shoes and rest, have a picnic lunch, and recharge your batteries.

Sights

Each town on Martha’s Vineyard has its own unique character. From the stately captains’ homes in Edgartown to the natural beauty of the Aquinnah Cliffs and the quaintness of Chilmark’s Menemsha Harbor, Martha’s Vineyard has a lot to see. But if you only have a day, then Oak Bluffs is the place to go. Everything is conveniently located within walking distance of the ferry, so you can spend more time exploring rather than getting from place to place.

Martha’s Vineyard Camp Meeting Association

The famous gingerbread cottages of Martha’s Vineyard can be found only a short stroll from the ferry docks. These cute summer homes are part of the Martha’s Vineyard Camp Meeting Association (MVCMA), colloquially known as “The Campground.” Originally, that’s just what it was, a campground. Beginning in 1835, the first Methodist retreat was conducted at this location. Tents were pitched and souls were saved as the participants gathered and prayed in the spot that was then known as Wesleyan Grove. As the retreats grew in numbers, serious prayer continued, but they also found time to enjoy some of the niceties of island life. Tents gave way to more permanent homes and eventually the elaborate trim and decorations that we see today.

At the heart of the campground is the Tabernacle, completed in 1879 to shield the worshipers from the hot summer sun. At the time, the MVCMA had connections with an iron builder and a civil engineer, and coupled with the lower cost of iron versus wood, built the structure for a total cost of $7,147.84. More can be learned about the campground during the Oak Bluffs Audio Tour, or through a more detailed live tour given by the MVCMA during the months of July and August.

MVCMA Tour Schedule

Live, guided walking tours of the Campground are given every Tuesday and Thursday in July and August only at 10:00 am and last approximately 90 minutes. Tours begin from the Tabernacle (click for map) and cost $12 per person. Tickets can be purchased at the start of the tour.

Visiting outside of peak summer season, or otherwise are unable to take the live tour through the Camp Meeting Association. No problem!. Stream the Knockabout Oak Bluffs Audio Tour anytime and start whenever you would like. 

Tabernacle/Trinity United Methodist Worship Services

Today, worship services continue at the MVCMA, although only on Sundays. Trinity United Methodist Church hosts services indoors on a year-round basis, and outdoors at the Tabernacle in summer. Trinity UMC welcomes worshipers of all denominations, so feel free to walk over and attend a service at this beautiful location.

Special Events

Aside from religious offerings, the campground hosts various weekly and special events throughout the summer, including weekly concerts on the Tabernacle lawn, community sings, and educational lectures. Some of these events may be a bit on the later side for the average day trip itinerary, should you be traveling over from the Cape. However, if they are of interest, you may wish to catch an evening ferry home so that you can enjoy these cultural events. For a full calendar of events, click HERE.

Grand Illumination

Cottagers decorate their homes (and sometimes themselves) for Grand Illumination, held annually on the third Wednesday in August. Photo by MA Office of Travel & Tourism, CC BY 2.0

Traditionally held on the third Wednesday in August, Grand Illumination is the capstone event in Oak Bluffs. On this night, the gingerbread cottages are decorated with hundreds of paper lanterns, setting the mood for a beautiful evening stroll through the campground. Although today it is hosted by the MVCMA, its origins date back to 1869 when the Oak Bluffs Land and Wharf Company sponsored the first Illumination night. This corporation had bought vast parcels of land just outside the campground for the development of Oak Bluffs as a tourist destination. It was not highly regarded by the Methodist campers who tried for years to isolate themselves from the growing number of secular tourists. However, times were changing and the MVCMA had to change with them. Eventually, Grand Illumination was accepted and then adopted by the campground. Today, it is considered their exclusive domain, and really nobody gives a thought as to how it all originated. But now you know…

If you are anywhere near Martha’s Vineyard on Wednesday, August 17, 2022, I do recommend that you attend.

African American Heritage Trail

Oak Bluffs is well known to be the summer retreat of wealthy African Americans, either as homeowners who stay for the entire season, or visitors who vacation for a week or two.  These days, the most well-known is former President Barack Obama, who during his two terms in office took annual vacations to Martha’s Vineyard and rented a home in Oak Bluffs. But other well-known visitors throughout history have included Jacki Robinson, Dr. Martin Luther King Jr., and Harry Belafonte.

The African American presence on the island had a more modest beginning, however. The first black residents started coming to the island in the late 19th century, sometime after the Civil War. They were freed slaves who came to work in the oil industry – whale oil, that is. But even then, whale oil was being phased out as an energy source, and soon the island transformed from an energy-producing mecca into a summer resort. The African-American folks stayed and by the 1930s, the black elite had started spending summers on the island, building a community that is very prominent to this day.

The African American Heritage Trail dissects the history of African Americans on Martha’s Vineyard and has 27 different sites of interest along its path. The trail offers tours throughout the summer months of varying lengths, so whether you want to spend an hour learning about this subject, or the entire day, there is a tour that should fit your schedule. Notable stops along the trail include the former homes of Edward Brooke, the first black senator elected by popular vote, and Dorothy West, author, and member of the Harlem Renaissance writer’s movement.

Flying Horses Carousel

Photo by MA Office of Travel & Tourism / CC BY-ND 2.0

Little ones will enjoy the carnival-like atmosphere of the Flying Horses, the oldest platform carousel in the nation. The carousel was manufactured in the mid-1870s and was originally put into service at Coney Island, NY. In 1884, the carousel was moved to Oak Bluffs, then known as Cottage City, to support the growing tourism economy on the island. After generations of turnover between private owners, the carousel was acquired by the Martha’s Vineyard Preservation Trust in 1986 and restored to its original beauty. The horses feature real horsehair manes and the carousel’s organ, built in 1923, still plays music from paper rolls. The property was designated as a National Historic Landmark in 1987.

Because of its early vintage, the carousel does not perform like its modern-day counterparts. Although the individual horses go round and round, they do not go up and down, making for a rather boring ride. So in order to capture the rider’s interest, the carousel features several dispensers where the rider attempts to grab as many metal rings as possible. The rings are then placed atop a spike on the horse’s head. Bragging rights go to the riders with the most rings, and a free ride goes to anyone who can snag a brass ring. Just remember that riders can only take rings with one hand. Reaching in with both hands is a safety violation and will cause a stern-faced attendant to come and confiscate all of your rings. I learned the hard way.

Beaches

Inkwell & Oak Bluffs Town Beach

Located right next to the Steamship Authority’s Oak Bluffs terminal, Inkwell & Town Beaches can get a bit congested in peak summer. Photo by MA Office of Travel & Tourism, CC BY-ND 2.0

Oak Bluffs is home to the Oak Bluffs Town Beach and Inkwell Beach, adjacent to each other. They are both within a few minutes’ walk from the harbor. Merely follow the ocean southbound until you bump into the sandy beach. There are a couple of stories on how Inkwell Beach got its name, although it is generally agreed upon that it is a reference to the African-American community that is prominent in Oak Bluffs, comparing the dark skin of beach-goers to that of an old fashioned bottle of writing ink. One legend is that the name was given by young, black writers who lived on the island during the summers. Another story is that it was initially a pejorative term given to the beach by intolerant persons from an intolerant time.  Whether the name was a badge of honor or a slight can be argued, but it is in the past for sure. Today, the Inkwell is the name embraced by islanders, and all are welcome to spread out and grab a few rays of sunshine or dive in the water to cool off.

Activities & Sports

After taking in some of the island’s history and culture, you may be up for something a little more extreme. Luckily, Oak Bluffs has some pretty great options for those who want to access their adventurous side. Don’t worry. This isn’t Yosemite. Things are a bit more chill here, and anyone that is reasonably fit should be able to enjoy these sports.

Stand Up Paddleboarding/Kayak Tours

Stand Up Paddleboarding (SUP) has seen tremendous growth throughout the nation in recent years, and for good reason. It can be learned quickly, requires only modest physical ability to enjoy, and can be done in most coastal and lake areas. Book a lesson or tour with one of the island’s SUP outfitters, and find out for yourself why so many people are taking to the sport.

A SUP tour will generally involve some basic instruction to keep you safe, including balancing on the board, staying clear of boat traffic, and what to do if the wind gets a bit too strong. Then, you’re off and paddling. Tour locations may be variable based on the wind and tidal conditions.

Kayak tours are also readily available throughout Martha’s Vineyard, and often can be booked through the same vendor. If someone in your group feels that (s)he cannot handle standing on a SUP for long durations, then you can combine your vessels of choice to accommodate everyone. Kayaks are generally more stable, best for those with uneasiness in the water, and require less physical exertion.

Island Spirit Kayak is Oak Bluff’s SUP and kayak outfitter and is located just a 5-minute drive away from the ferry terminal. Take an Uber or taxi to “Little Bridge” at the State Beach in Oak Bluffs. Alternatively, jump on the #13 bus to Edgartown and tell the driver that you want to get off at Little Bridge.

That being said, make sure you call ahead to book your reservation and ensure that boards/kayaks will be available.

Flyboarding, Parasailing & Jet Ski Rentals

If you’re seeking a thrill, or more likely your teenage kids are complaining that your walkabout through town is getting too boring, then head on over to Oak Bluffs Harbor and try out this fun adventure sport. Flyboarding involves strapping on a board with water jets to your feet, powered by a jet ski engine and attached by a 50-foot fire hose. Riders can feel like Iron Man as they fly over the waters of Vineyard Sound. This is an experience that few can say they have tried, and sure to be a highlight of your vacation.

Flyboarding should be able to satiate the appetite of adventure-hungry teens and adults alike.

Martha’s Vineyard Ocean Sports is located on Oak Bluffs Harbor at the Dockside Marina and is the only flyboarding and parasailing vendor on the island. They also offer a multitude of additional ocean sports activities like jet ski rentals, water-skiing, and family banana boat rides. Make sure to call in advance or book online via their website to secure your slot. This will allow you to plan around your adventure and maximize your time.

Pirate Adventures

Oak Bluffs Harbor is home to Pirate Adventures, a 90-minute experience designed to immerse the little buccaneers of your family in a live-action pirate story. Sail aboard the Sea Gypsy in search of buried treasure, engage in a sea battle with enemy pirates where the young adventurers will blast the scallywags with water cannons mounted on the side of the ship.

Activities that are geared toward young children are not very plentiful on Martha’s Vineyard, so you may want to take advantage of this adventure if traveling with young kiddos. My kids did this adventure when they were younger and loved it.

Bike Rental

Photo by Lisa Brown/MA Office of Travel and Tourism, CC BY-ND 2.0

Martha’s Vineyard is home to some excellent bicycle trails and offers the day-tripper a way to see more of the island while being active. Renting a bike is an excellent way to explore the down-island towns. You could cycle up to East Chop Lighthouse, or pedal the six-mile route south to Edgartown along Beach Road and even explore the more tranquil scenery of Chappaquiddick Island. Depending on your level of ambition, there is a bike route that will suit your desires. And remember, Vineyard Transit Authority buses are equipped with bike racks, so if for some reason you don’t want to leg it back to Oak Bluffs, you can always catch a cheap ride.

There are plenty of bike rental shops in the center of Oak Bluffs. You won’t have trouble finding them. However, below is a list of vendors and a consolidated map for your convenience. Advance reservations are not necessary.

• All-Star Bike Rentals
• Pedago Martha’s Vineyard (Rents both pedal and electric bicycles)
• Anderson’s Bike Rentals

The Martha’s Vineyard Chamber of Commerce publishes a map with island bike paths (no motor traffic) and bike routes (roads shared with traffic, but generally suitable for bicycles). This is a valuable resource if you are planning a day that involves commuting by bicycle. It may be downloaded free through their website by clicking the link below.

Martha’s Vineyard Bike Trail Map

** A note on renting mopeds and scooters. Don’t do it! Many of the roads on Martha’s Vineyard are narrow, winding, sandy, and filled with cars whose drivers are unfamiliar with the roads. I used to work as a physical therapist at Martha’s Vineyard Hospital. I can tell you that people do get hit by cars, and have seen more than one vacation ruined by broken bones. There were many others that I didn’t see because they were shipped off to Boston via Med Flight. Electric bicycles are a good alternative to mopeds if you desire. You will be able to access the bike trails and stay much safer.

Food & Drink

Oak Bluffs boasts the most restaurants and pubs on the island. You will find no shortage of places to satisfy your hungry belly or quench your thirst. From sit-down table service to quick street fare, it can all generally be found in one of two places: Circuit Ave or the Dockside Marina. Both are within shouting distance of each other, so feel free to mix food at one location with a specialty drink someplace else.

Circuit Avenue

The Oak Bluffs Land and Wharf Company built Circuit Ave as the commercial hub of town back in the late 1800s, and it remains so today. Named after its partial envelopment of the MV Camp Meeting Association Campground, this street continues to draw visitors due to its high concentration of retail stores as well as eating and drinking establishments.

Sharky’s Cantina

Sharky’s is open year-round, which means it has a menu and service that is good enough to draw people back repeatedly during the cold off-season months. Serving traditional Mexican fare in a Grill & Bar type atmosphere, Sharky’s may hit the spot if you’ve already indulged in enough New England seafood. For those who want more, the fish tacos are recommended.

Offshore Ale Company

Skip the ocean view and instead enjoy some of the Vineyard’s locally made beer and a wide selection of pub food to go along with it. Offshore Ale is one of the most popular spots with locals year-round, and the craft brew that it serves is first-rate. Beers on tap rotate, with about 10 selections to choose from at any given time. The brewery has definitely followed the current craze of IPA and other hop-beatdown style beers, but also offers less bitter ales including nut brown, amber, and light beer.

Offshore Ale‘s menu probably has one of the widest selections in town. Chowders and seafood, burgers, pizza, and quesadillas are all up for grabs. Family-friendly during lunch and dinner hours.

Giordano’s

The best pizza in town. Giordano’s has both sit-down service as well as a take-out window. Let’s say that you have been walking around town all day and need a bit of space between you and the nearest crowd. Grab a pie and walk over to the open lawn at Ocean Park and have a picnic. Spread out and decompress. Giordano’s also has the typical fried seafood options, and a basket of clams to go along with your pizza is actually a pretty good combo, as odd as it might sound.

Ben and Bills Chocolate Emporium

Are you in the mood for something sweet? Stop in for some house-made chocolate. You can even see them making it as you shop around. They also serve delicious homemade ice cream that rivals any other on the island.

Dockside Marina

Just a few steps from the base of Circuit Ave is Oak Bluffs Harbor, home to the Dockside Marina and its tenant eating and drinking establishments. In contrast to the Bar & Grill Feel that you might get from the options on Circuit Ave, you will find a more tropical atmosphere here (even though we are nowhere near the tropics). Boats in the slips play Jimmy Buffet all day long, and there is a constant flow of frozen rum drinks coming from the blenders of nearby bars. If you haven’t felt it yet, you are now on Island Time. If you’re wearing a watch, just take it off now. You’ll get home when you get there.

Nancy’s/Donovan’s Reef

Donovan’s Reef is the outdoor bar area of Nancy’s Restaurant, home of the famous Dirty Banana and a little piece of the Caribbean brought north to Martha’s Vineyard. From the reggae music to the pitchers of frozen concoctions served by Donovan himself, you’ll immediately feel a bit more relaxed when you step up to the bar. Donovan, who is from Jamaica, has been working the reef for 20 years and is an attraction unto himself. Really, it’s not just that people want a Dirty Banana. They want to see Donovan making it, too. If you’re lucky, he will be on shift when you arrive.

Nancy’s has all of the items that you might expect from a waterfront restaurant, including whole lobster, clam chowder, and fried and broiled seafood platters. Table service is found upstairs and on the top deck, while walk-up service is outside on the patio.

Coop DeVille

Also located directly on the harbor, “The Coop” offers up amazing views and sunsets while you take in a meal or a few drinks. Outdoor, covered seating is available which is a nice option when you have been in the sun all day and need a break. The atmosphere is distinctly casual, and when you arrive, it feels like this is the place to get messy with a whole, boiled lobster or maybe a basket of steamer clams and a beer. The Coop also has a full raw bar for those who like slurping oysters on the half shell.

Lookout Tavern

Lobster Roll from the Lookout Tavern, a very popular stop in Oak Bluffs

Overlooking the water on Vineyard Sound is an old five-bedroom cottage that has been remodeled into a pretty happening place. If you like sushi, then this is the place to get it. The Lookout also serves traditional American Raw Bar fare, as well as battered and fried seafood, burgers, and grilled dishes. From the outside deck, you can see the ferries of the Steamship Authority pull into the pier, so this also makes a great place to stop and relax as you wait for your boat to the mainland.

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