The Vineyard

Martha’s Vineyard or “The Vineyard” as it sometimes called has no shortage of history or lore. Originally inhabited by the Wampanoag people, the Island was known in the Massachusetts language as Noepe or “land amid the streams.” As it grew in popularity and renown, the Island became a swank destination for dignitaries, artists, and titans of industry alike. Not much has changed throughout the years as modern day presidents, celebrities, and vacationers flock to the small piece of paradise off the Cape Cod coast. With nineteen beaches, a plethora of restaurants offering unique farm (or sea)-to-table delights, and attractions ranging from art to music to eco-tourism, The Vineyard remains one of the most awe-inspiring places in the world.

Oak Bluffs

Fun, colorful and eclectic, Oak Bluffs is arguably, the best town on the island.

Restaurants within walking distance

$Thai cuisine, Dos Mas, MV Salads, Linda Jeans, Fat Ronnies, Giordano’s pizza slices
$$Offshore Ale, Nancy’s, Lobsterville, Coope de Ville, Fishbones, The Lookout, Sarah Browns , Giordano’s
$$$The Sweet Life Café, Jimmy Seas, The Red Cat, The Cardboard Box, The Oyster Bar 02557, MV Chowder Company

Special Occasion dining in Oak Bluffs
 The Sweet Life Café, The Red Cat, The Oyster Bar 02557


Withing walking distance: Oak Bluffs town beach, the Inkwell, East Chop beach
A short drive or bike ride: State Beach.  Jump off The Jaws Bridge or rent SUP boards or kayaks form Island Spirit Kayaks
There are many beaches on the island, further from the Inn.

Things to Do

Walk among the 300+ carpenter gothic gingerbread style cottages of the Martha’s Vineyard Camp Meeting Association, visit some of the sites on the African American Trail, fly a kite and have a picnic in Ocean Park, ride the Flying Horses carousel, try your luck at casting a line on the town Fishing Pier, browse the unique and eclectic shops on Circuit Avenue, eat fresh seafood on the harbor while enjoying the sunset and much more.  Visit The East Chop Light House a great walk or run a mile out of town.


Located six miles from Oak Bluffs is the historic whaling town of Edgartown.  Greek revival architecture define this town.  Travel there by The #13 bus, ride a bike on the bike path along beautiful State Beach, Taxi or Uber


$ The Quater Deck, The Newes Pub, Sharky’s Bad Martha Brewery

$$ The WharfThe Seafood Shanty, The Newes Pub

$$ $ The Port Hunter, Atria, Detente ,


Lighthouse beach, South Beach

Things to do

The Edgartown Light House is a short walk from the center of town.  The Carnegie Museum  is a small museum where various walking tours depart from. Take The On Time Ferry to Chappaquiddick  and take  The Cape Pogue Lighthouse Tour  Also check out Mytoi, a Japanese garden there. Great shopping and walks around town

Vineyard Haven

Located three miles from Oak Bluffs is the year round ferry town of Vineyard Haven.  Travel there by The #13 bus, or cycle there via The East Chop Light House or taxi or Uber.


$ The Net Result, The Art Cliff Diner, Frankie’s Market

$$ The Black Dog Tavern, Waterside Market , Mikado, Copper Wok

$$$ Garde East, La Soffitta, Beach Road Restaurant


Eastville, by the drawbridge, Tashmoo

Things to do

The Martha’s Vineyard Museum is awesome.  Set up a time online to visit and take the short walk out of town there.  On the way you can also stop by Chicken Alley, a thrift store like no other.  Check out great shops on Main Street like The Green Room, LeRoux, and Nochi. Walk along  Historic Williams Street.  When you get to the end of town, go down to the water via Owen Park and walk along the beach back to the bus stop.  If you have a bike or car, take Main St. three miles out of town to The West Chop Light House.  Unfortunately, this is the only light house on the island that you can’t walk up to or go in.  Fortunately, if you continue on the road, there is an awesome look out by the flag pole.  Commanding views of Vineyard Sound and Woods Hole from this bluff, and awesome sunsets.

Up Island

The three rural towns of West Tisbury, Chilmark, and Aquinnah make up the western end of the island.  Called “Up Island” because latitude increases as you go west.  The Gay Head Light House on the extreme western end of the island is a forty five minute drive from Oak Bluffs.  There is bus service to get there but requires multiple routes.


$ 7A, Chilmark General Store

$$ Larsen’s Fish Market, Menemsha Fish Market, Aquinnah Restaurant

$$$ Chilmark Tavern, Outermost Inn, State Road Restaurant


Long Point, Menemsha, Moshup Beach, Great Rock Bight


I did not know what to expect when we arrived. But the moment we stepped foot onto the property, I felt like I was home. Fresh baked cookies and absolutely the best lemonade. The owner Erik, is simply amazing, very informative, friendly, like the Big Brother type. The rooms were comfortable and clean. I am sooooo happy to have vacationed at this Bed and Breakfast. Looking forward to making this my annual spot. Kudos to Oak Bluffs Inn, job well done!!

Stephanie Tammy Napier