Destination Main Streets

Oak Bluffs (Martha's Vineyard), Massachusetts

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Oak Bluffs was our first stop on our whirlwind tour of Marth's Vineyard. We arrived by ferry from Hyannis on Cape Cod. Oak Bluffs was originally founded as a resort town and has been long known for its beautiful architecture, including its Gingerbread Cottages. Once we finished our visit in Oak Bluffs, we continued on to Edgartown and Vineyard Haven, two other Main Street communities on the island.

Oak Bluffs is located in Dukes County, Massachusetts, which is mostly made up of Martha's Vineyard. You cannot drive directly to the town by car from the mainland, but you can take the ferry from Hyannis. There is another ferry that connects Woods Hole on Cape Cod to Oak Bluffs or to nearby Vineyard Haven. The ferries dock right in the heart of Oak Bluffs so you can easily walk around. Circuit Avenue is the town's Main Street, but other businesses can be found along Oak Bluffs Avenue closer to the docks and the harbor.

Photo Gallery

To get to Martha's Vineyard we took the ferry from Hyannis to the town of Oak Bluffs on the northern coast of the island.  This the first town we'll hit on our tour of Martha's Vineyard, but we'll also hit Edgartown and Vineyard Haven as well.
To get to Martha's Vineyard we took the ferry from Hyannis to the town of Oak Bluffs on the northern coast of the island. This the first town we'll hit on our tour of Martha's Vineyard, but we'll also hit Edgartown and Vineyard Haven as well.
Here's a view of Oak Bluffs from the ferry as we were just about to dock.  Oak Bluffs is home to lots of wonderful architecture and is famous for it's Gingerbread Cottages.
Here's a view of Oak Bluffs from the ferry as we were just about to dock. Oak Bluffs is home to lots of wonderful architecture and is famous for it's Gingerbread Cottages.
Like the rest of the town, the area around the marina is filled with restaurants and shops.  It was also around here that we picked up a rental car to get around to the other towns on Martha's Vineyard.
Like the rest of the town, the area around the marina is filled with restaurants and shops. It was also around here that we picked up a rental car to get around to the other towns on Martha's Vineyard.
Here's a small indoor mall close to the docks.  Inside you'll find shops, restrooms, and a visitor information.
Here's a small indoor mall close to the docks. Inside you'll find shops, restrooms, and a visitor information.
This is the intersection of Oak Bluffs Avenue, Lake Avenue, and Circuit Avenue pretty close to the heart of town.  There's a small information kiosk on the corner.  Behind it, along Oak Bluffs Avenue, you can see the Strand Theatre.  At the time we were there it was not showing movies but was instead occupied by an apparel store.
This is the intersection of Oak Bluffs Avenue, Lake Avenue, and Circuit Avenue pretty close to the heart of town. There's a small information kiosk on the corner. Behind it, along Oak Bluffs Avenue, you can see the Strand Theatre. At the time we were there it was not showing movies but was instead occupied by an apparel store.
Around the corner at the intersection of Kennebec Avenue and Lake Avenue is the Trinity Episcopal Church.  Notice the cedar siding that's typical in New England.
Around the corner at the intersection of Kennebec Avenue and Lake Avenue is the Trinity Episcopal Church. Notice the cedar siding that's typical in New England.
Across from the church along Lake Avenue is this quaint block, including Giordano's Restaurant.
Across from the church along Lake Avenue is this quaint block, including Giordano's Restaurant.
At the southeast corner of the intersection of Lake Avenue and Kennebec Avenue is this cafe serving bagels and ice cream.
At the southeast corner of the intersection of Lake Avenue and Kennebec Avenue is this cafe serving bagels and ice cream.
We head back over to Oak Bluffs Avenue.  Notice some of the businesses here include bike rentals and even car rentals.  We're still not far from the docks where folks reach the island by ferry.
We head back over to Oak Bluffs Avenue. Notice some of the businesses here include bike rentals and even car rentals. We're still not far from the docks where folks reach the island by ferry.
A shopper checks out the merchandise along Oak Bluffs Avenue.  Notice the restaurant there selling chowder.  They also have good lobster rolls.
A shopper checks out the merchandise along Oak Bluffs Avenue. Notice the restaurant there selling chowder. They also have good lobster rolls.
Here's a view of Ocean Park.  The large Victorian houses back there have a great view of the park and Nantucket Sound just on the other side of it.  Oak Bluffs is one of the earliest planned communities in the nation.  And it was planned from the ground up as a resort town.  Its architecture has long been an attraction going as far back as the nineteenth century.
Here's a view of Ocean Park. The large Victorian houses back there have a great view of the park and Nantucket Sound just on the other side of it. Oak Bluffs is one of the earliest planned communities in the nation. And it was planned from the ground up as a resort town. Its architecture has long been an attraction going as far back as the nineteenth century.
Now we start heading south along Circuit Avenue.  A large number of shops and other businesses are along this street, making it the closest thing to Oak Bluffs' Main Street.  This is a view looking north towards the intersection of Circuit Avenue, Lake Avenue, and Oak Bluffs Avenue.
Now we start heading south along Circuit Avenue. A large number of shops and other businesses are along this street, making it the closest thing to Oak Bluffs' Main Street. This is a view looking north towards the intersection of Circuit Avenue, Lake Avenue, and Oak Bluffs Avenue.
Bar and Grills and stores selling clothing and accessories line the zero hundred block of Circuit Avenue.
Bar and Grills and stores selling clothing and accessories line the zero hundred block of Circuit Avenue.
Mad Martha's is a local ice cream chain featuring some pretty innovative flavors.  For a taste of New England you can try the Maple Walnut or even the Lobster ice cream.
Mad Martha's is a local ice cream chain featuring some pretty innovative flavors. For a taste of New England you can try the Maple Walnut or even the Lobster ice cream.
Here's another view from in front of Mad Martha's, this time looking south down towards several other shops and restaurants.
Here's another view from in front of Mad Martha's, this time looking south down towards several other shops and restaurants.
Across the street are more shops, restaurants, and even another ice cream parlor.  The building on the left side of the picture is a large arcade.  Also, notice that there is no on-street parking on the west side of Circuit Avenue.  You can only park on the east side.  Plus, all traffic is one-way southbound.
Across the street are more shops, restaurants, and even another ice cream parlor. The building on the left side of the picture is a large arcade. Also, notice that there is no on-street parking on the west side of Circuit Avenue. You can only park on the east side. Plus, all traffic is one-way southbound.
This restaurant recently got a fresh coat of paint.  And check out the detail on those shutters.
This restaurant recently got a fresh coat of paint. And check out the detail on those shutters.
The Corner Store is a large general store selling groceries and beach gear.  The small park next to it looks like a pedestrian walkway that was once a road.
The Corner Store is a large general store selling groceries and beach gear. The small park next to it looks like a pedestrian walkway that was once a road.
Here's another view of that small pedestrian area.  Despite the pavement, it has a nice park-like feel to it.  In fact, it leads to Park Avenue, which leads out to Ocean Park, which we were looking at earlier.
Here's another view of that small pedestrian area. Despite the pavement, it has a nice park-like feel to it. In fact, it leads to Park Avenue, which leads out to Ocean Park, which we were looking at earlier.
The Nashua Hotel is one of many places to stay while in Oak Bluffs.  It's also a fine example of Victorian architecture.  This is on Park Avenue as well.  At this point, I turned around and headed back to Circuit Avenue.
The Nashua Hotel is one of many places to stay while in Oak Bluffs. It's also a fine example of Victorian architecture. This is on Park Avenue as well. At this point, I turned around and headed back to Circuit Avenue.
We're back on the zero hundred block of Circuit Avenue where we find more clothing stores and restaurants.
We're back on the zero hundred block of Circuit Avenue where we find more clothing stores and restaurants.
This building, known as The Arcade, was built in 1871 and in its past served as a post office and a library.  Today it's occupied by multiple businesses, including this bar and grill.
This building, known as The Arcade, was built in 1871 and in its past served as a post office and a library. Today it's occupied by multiple businesses, including this bar and grill.
Here's another shot with The Arcade on the left.  We're facing north here, looking back on the way we came.
Here's another shot with The Arcade on the left. We're facing north here, looking back on the way we came.
This is a view facing south on Circuit Avenue.  Notice again how traffic is one-way heading southbound.  Also, as you can see, on-street parking is only on the east side of Circuit Avenue.
This is a view facing south on Circuit Avenue. Notice again how traffic is one-way heading southbound. Also, as you can see, on-street parking is only on the east side of Circuit Avenue.
Here's a view of a t-shirt and gift shop on Circuit Avenue.  Having no cars on the west side of Circuit Avenue makes it easier to take good pictures in this direction.
Here's a view of a t-shirt and gift shop on Circuit Avenue. Having no cars on the west side of Circuit Avenue makes it easier to take good pictures in this direction.
Notice the crosswalk on the bottom right-hand corner of the screen.  Circuit Avenue is relatively pedestrian friendly with slow moving traffic.  Also, notice the yellow shop?  It's one of the many gingerbread cottages you can find around town in Oak Bluffs.
Notice the crosswalk on the bottom right-hand corner of the screen. Circuit Avenue is relatively pedestrian friendly with slow moving traffic. Also, notice the yellow shop? It's one of the many gingerbread cottages you can find around town in Oak Bluffs.
A row of signs on Circuit Avenue, featuring a variety of styles and merchandise.  Most of these shots were taken in the morning so the pictures on the westside of the street came out much better.
A row of signs on Circuit Avenue, featuring a variety of styles and merchandise. Most of these shots were taken in the morning so the pictures on the westside of the street came out much better.
Here's that same row of shops again but this time with a wider shot aimed north bound back the way we came.
Here's that same row of shops again but this time with a wider shot aimed north bound back the way we came.
This is a row of shops along the east side of Circuit Avenue where it's a bit shadier.  See the picture of the frog on the sign?  It's in the shape of the island of Martha's Vineyard.
This is a row of shops along the east side of Circuit Avenue where it's a bit shadier. See the picture of the frog on the sign? It's in the shape of the island of Martha's Vineyard.
Here's another view of those same shops.  The frog is a little easier to see in this picture.  You can also see that it's shadier here during this time of the morning.
Here's another view of those same shops. The frog is a little easier to see in this picture. You can also see that it's shadier here during this time of the morning.
At the intersection of Circuit Avenue and Kennebec Avenue is the Union Chapel built in 1870.  With its octagonal shape and great accoustics, this non-sectarian chapel is a popular venue and place to get married.
At the intersection of Circuit Avenue and Kennebec Avenue is the Union Chapel built in 1870. With its octagonal shape and great accoustics, this non-sectarian chapel is a popular venue and place to get married.
We're almost to the end of Circuit Avenue.  Check out that large pink house at the intersection of Circuit Avenue and Narragansett Avenue.
We're almost to the end of Circuit Avenue. Check out that large pink house at the intersection of Circuit Avenue and Narragansett Avenue.
Here's a candy store close to the end of the Circuit Avenue business district.
Here's a candy store close to the end of the Circuit Avenue business district.
And across the street is another large pink structure.  This one is The Oak Bluffs Inn, a very distinctive building with a huge cupola on the roof.
And across the street is another large pink structure. This one is The Oak Bluffs Inn, a very distinctive building with a huge cupola on the roof.
This is a small pharmacy on Pennacook Avenue.  This is where we turned around and got in our car and headed to the other towns on Martha's Vineyard.  Edgartown and Vineyard Haven.  But later, we came back to Oak Bluffs, so our photo tour here isn't quite over yet.
This is a small pharmacy on Pennacook Avenue. This is where we turned around and got in our car and headed to the other towns on Martha's Vineyard. Edgartown and Vineyard Haven. But later, we came back to Oak Bluffs, so our photo tour here isn't quite over yet.
We're back in Oak Bluffs and the sun is starting to set.  People are out and eating and drinking with excellent views of the water and the boats.
We're back in Oak Bluffs and the sun is starting to set. People are out and eating and drinking with excellent views of the water and the boats.
There are plenty of restaurants to choose from around here, all with excellent waterfront views.  At this point we weren't far from where we needed to pick up the ferry for our return trip back.
There are plenty of restaurants to choose from around here, all with excellent waterfront views. At this point we weren't far from where we needed to pick up the ferry for our return trip back.
Not content to sit and wait for the ferry, I grabbed my camera and continued taking pictures.  There are also plenty of shops around here.  Including this one located in a New England style structure on the corner of Lake Avenue and Central Avenue.
Not content to sit and wait for the ferry, I grabbed my camera and continued taking pictures. There are also plenty of shops around here. Including this one located in a New England style structure on the corner of Lake Avenue and Central Avenue.
This is another view of the docks and the boats and yachts parked for the evening.  We saw quite a bit of partying happening on some of these yachts.  Also, notice the gingerbread on that blueish house in the background.
This is another view of the docks and the boats and yachts parked for the evening. We saw quite a bit of partying happening on some of these yachts. Also, notice the gingerbread on that blueish house in the background.
Here's a row of beautiful and well-maintained cottages along Lake Avenue with an excellent view of the water across the street.
Here's a row of beautiful and well-maintained cottages along Lake Avenue with an excellent view of the water across the street.
Also along Lake Avenue, the Wesley Hotel is the largest ocean-front hotel on Martha's Vineyard.  It also has excellent views of the harbor.
Also along Lake Avenue, the Wesley Hotel is the largest ocean-front hotel on Martha's Vineyard. It also has excellent views of the harbor.
Soon we were on the ferry and heading back to Hyannis across Nantucket Sound.  Here's a view of the sun setting on the horizon over Martha's Vineyard.
Soon we were on the ferry and heading back to Hyannis across Nantucket Sound. Here's a view of the sun setting on the horizon over Martha's Vineyard.

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Oak Bluffs Association
Oak Bluffs Marina
Town of Oak Bluffs

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