Oak Bluffs, Martha's Vineyard

Oak Bluffs, Martha's Vineyard

Oak Bluffs

The town of Oak Bluffs, nestled on the Island of Martha’s Vineyard, is one of the most famous seaside Victorian towns in New England the United States at large. Once known as Cottage City.

Places to Visit

  • Gingerbread Cottages – Get lost in the Martha’s Vineyard Camp Meeting Association with its maze of lovely, decorated cottages, Tabernacle and Museum. Once a true “campground” where revivals were held, one can now enjoy concerts, art exhibits, walking tours, sightseeing and more.
  • Flying Horses Carousel - The Flying Houses Carousel is the nation’s oldest platform carousel. Since 1884, the Flying Horses Carousel has delighted visitors in the town of Oak Bluffs.
  • Ocean Park - A charming Oak Bluffs park surrounded by Victorian mansions and gingerbread houses. The park features a bandstand which holds weekly band concerts during the summer.
  • Inkwell Beach - This Oak Bluffs beach and surrounding area of colorful gingerbread Victorian houses have strong links to African-American heritage on Martha's Vineyard, dating back to the Revolutionary War. The Polar Bears, a community group of predominantly African American women who hold early morning prayer and swimming sessions, can be found at this beach in the early morning hours from the beginning of summer through Columbus.
  • Joseph Sylvia State Beach - In Oak Bluffs the Joseph Silva State Beach extends down the Beach Road toward Edgartown. Parking and access are easy here as well as at the Oak Bluffs Town Beach, which starts at the OB Steamship dock and extends out well beyond Ocean Park.
  • African American Heritage Trail – The trail celebrates the stories of African American people on the Island. There are bronze markers on the 30 selected sites that tell the story.
  • Oak Bluffs Harbor - A landlocked basin protected by two breakwaters. Oak Bluffs Harbor is a popular destination for pleasure boats.
  • The Oak Bluffs Marina is the largest marina on Martha's Vineyard, with 81 slips and 50 moorings, fuel and pump-out facilities
  • East Chop Lighthouse - East Chop Light is a historic lighthouse standing on a bluff overlooking Vineyard Haven Harbor and Vineyard Sound, located along East Chop Drive in the town of Oak Bluffs, Massachusetts. It is one of five lighthouses located on the island of Martha's Vineyard.
  • Niantic Park – Tennis, Basketball, Pickle Ball, Swing Sets and FUN FOR YOUNG AND OLD ALIKE!!!

Things to Do

  • Harbor Festival -Each year Harbor Festival surpasses the record crowds of the previous year. Over 40 vendors from near and far, including many of the Vineyard favorites plan to return for one of the Island’s most popular events. Local artists, craftsmen and antique dealers, as well as non-profit organizations offering a tempting array of baked goods, raffles and information about their causes, will be on hand.
  • Tivoli Day - Wave goodbye to summer and join the annual Tivoli Day street fair and block party. Tivoli Day, an old-fashioned September festival downtown Oak Bluffs has been MV's tradition for 4 decades. It's a day to celebrate all the hard work of the summer and to welcome beautiful Island fall.
  • Union Chapel - Built as a non-sectarian place of worship in 1870, Union Chapel’s unique octagonal design rises into a soaring open cupola with diamond-pane glass windows. Its excellent acoustics, ethereal airy interior, and seating in the round makes an event in this structure intimate a memorable experience.
  • Wind Festival - Events include kite making and model sailboat racing for children, and kite flying and frisbee games for young and old. There will be prizes for all ages in the categories listed on this site.
  • Ladyfest - an annual music festival held on Circuit Avenue in Oak Bluffs, MA and presented by The Ritz Cafe on the island of Martha's Vineyard
  • Craft Beer Festival - The Martha's Vineyard Craft Beer Festival features ~50 Breweries, ~150 Brews, 5 Bands, Fun Games, Local Food & Super Cool Vendors from all over!!
  • Back Door Donuts – A bakery and coffee shop but once the sun sets, the back door swings open. With it, the sweet smells of sugary summer pour out!
  • **Featherstone Center for the Arts **- Featherstone Center for the Arts is a vibrant community art center offering year-round arts education and experiences for all ages and abilities on Martha's Vineyard. Galleries, studios and outdoor spaces provide creative outlets for visitors, students and artists.
  • Christmas Tree Lighting - Come and join the fun in Post Office Square as Oak Bluffs kicks off the holiday season with its annual tree lighting accompanied by the Vineyard Brass Ensemble, lots of hot chocolate, antlers for the young and of course the arrival of Santa!
  • Halloween – Trick or Treat on Circuit Ave.!
  • Oak Bluffs Blue Water Classic – This annual fishing event is held at the Oak Bluffs Marina.
  • Martha’s Vineyard Striped Bass and Bluefish Fishing Derby - Come to the Vineyard and fish the Derby!
  • Bowling Alley – There is bowling in Oak Bluffs at the Barn Bowl and Bistro!
  • Strand Movie Theater – The latest and greatest movies in downtown Oak Bluffs!
  • The Ritz-Live Music Dancing – Famous Oak Bluffs Dive Bar! Great music and food!
  • YMCA – 508 696-7171 Dedicated to improving the quality of life for children, individuals, families and the Island community by helping members realize their fullest potential through the development of body, mind, and spirit.
  • Skateboard Park
  • **Bike Path **
  • Tennis Courts – Niantic Park
  • Pickle Ball – Niantic Park
  • Basketball – Niantic Park
  • Camping – Martha’s Vineyard Camp Grounds
  • Sailing Camp
  • Golf Course – Farm Neck
  • Tradewinds Airfield
  • Swimming – Inkwell and State Beach and the YMCA
  • Fishing Charters
  • MV Steamship Authority 508-477-8600
  • Sea Streak Fast Ferry – Boat to New Bedford 1-800-BOATRIDE
  • MV Fast Ferry 401-295-4040
  • HY-Line Cruise 800 492 8082
  • Island Queen – Boat to Falmouth 508-548-4800
  • Patriot Boat – Boat to Falmouth 508-548-2626
  • Playground – Niantic Park
  • Corner Store 508-693-1470
  • Basics Clothing 508-693-8819
  • Hollywood Nails 508-338-2482
  • Souvenirs – Shops on Circuit Ave
  • Ice Cream – Ben & Bills 508-696-0008
  • Mad Martha’s 508-693-9152
  • Rosies Frozen Yogurt 508-687-0031
  • Free Concerts – Sundays in the Bandstand Gazebo in Ocean Park
  • Public Restrooms – There are four in town: One in the brick building near the fishing pier and Steamship Authority Terminal, one in the Steamship Authority Terminal, one near Our Market for wine, liquor and other conveniences, one near B-Strong Gym on Kennebeck Avenue
  • Barbershop – Benito’s is the place to go on Circuit Ave. for a close shave and haircut.
  • Nail Salon – Hollywood Nails
  • Jewelry Store - Driftwood
  • Gift Shop – Glimpse of Tibet

Good Eats

  • Best Fried Clams – Lobsterville Bar and Grill 508-696-0099
  • Nancy’s Restaurant – Obama eats here! 508-693-0006
  • Giordanos Pizza Seafood Italian Dinners 508-693-0184
  • Off Shore Ale 508-693-2626
  • Lookout Tavern 508-696-9844
  • Redcat 508-696-6040
  • Sweetlife 508-696-0200
  • Mocha Motts – coffee bagels 10 Circuit Ave 508-696-1922
  • Toccopurro – coffee 45 Circuit Ave 508-338-2463


  • Anchor Real Estate – THE BEST agents on Martha’s Vineyard 508-696-7777
  • Bank – ATM – There are several throughout downtown
  • Charter Fishing
  • Bike Rental – Anderson’s Bike Rental
  • Moped Rental
  • Car Rental – A-A Island Auto Rental 1-800-627-6333
  • Budget — 508-693-1911
  • Hertz — 508-693-4196

Worth a Look

  • Black Dog - Out of one sailing Captain's love for the sea, his island home, and of course, his dog, The Black Dog Brand was born.
  • Vineyard Vines - An American clothing and accessory retailer founded in 1998 on Martha's Vineyard
  • Backdoor Donuts 508-693-3688 open during the day or wait in line late night
  • Reliable Market 508-693-1102
  • DaRosa’s 508 693-0110
  • Phillips Hardware 508-693-0377
  • Ben & Bills Chocolate 508-696-0008
  • Corner store 24 Circuit 508-693-1470
  • Basics Clothing 24 Circuit 508-693-8819
  • Hollywood Nails 40 Circuit 508-338-2482
  • Ice Cream – 20 A Circuit Ben & Bills 508-696-0008
  • Mad Martha’s 508-693-9152, Carousel 508-
  • Rosies Frozen Yogurt 19 Circuit 508-687-0031
  • Free Concerts – Sundays in the Bandstand Gazebo in Ocean Park
  • Public Restrooms – There are four in town: One in the brick building near the fishing pier and Steamship Authority Terminal, one in the Steamship Authority Terminal, one near Our Market for wine, liquor and other conveniences, one near B-Strong Gym on Kennebeck Avenue
  • Barbershop – 38 Circuit 508-696-0033 Benito’s is the place to go on Circuit Ave. for a close shave and a haircut.
  • Rentals MV LINEN RENTAL 774-563-5843
  • Morning Glory Farm 508-627-9003
  • Flying Horses 508-693-9481
  • Game Arcade Ryan Amusements 508-687-9179
  • Kayak Rentals – Island Spirit Kayak and Wind’s Up
  • Water Sports – MV Ocean Sports
  • Bus Transportation – VTA 508-693-9440
  • Information Booth - This info center is near the ferry and bus terminal. You can grab a map and brochures to find out about the areas restaurants, bars and attractions.
  • Gift Shops – Craftworks, Sanctuary
  • Fireworks in Ocean Park – Join the thousands!!!!
  • Illuminations - Thousands of Island residents and visitors enjoy Grand Illumination each summer and this year we are celebrating the Sesquicentennial of this cherished annual event.
  • All Island Tours 774-327-8192
Previous Post
Up Island West Tisbury, Martha's Vineyard
Next Post
Island Info for Martha's Vineyard

Martha's Vineyard Real Estate Properties By Town

Martha's Vineyard Real Estate Properties By Type