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A summer evening in Oak Bluffs with waterfront dining at Jetty Beach House (the old Lobsterville Bar and Grille building), sunset harbor views, and a scenic ride to Vineyard Haven.
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Oak Bluffs has a handful of waterfront restaurants worth planning an evening around. The main three today are Jetty Beach House (in the old Lobsterville Bar and Grille building), Nancy's, and Sand Bar, all on the water, each with a different feel.
Lobsterville Bar and Grille sat directly on the water, and from a table there you could watch the sun go down over the harbor. In 2026 the building reopened as Jetty Beach House, so the view is still on the menu. The kitchen does fresh seafood; a lobster roll and a drink while the light fades is a hard combination to beat. It draws locals as well as visitors, which is usually a good sign.
Sunset over the water from a waterfront railing.
The sky going orange behind the rooflines as the sun drops toward the water.
Nancy's runs a broad menu, seafood through burgers, and handles families and bigger groups well. The upstairs bar has a good angle on the sunset. It is seasonal: Nancy's is closed now and plans to reopen in May 2027.
Sand Bar is the casual one: open-air, beachside, food and drinks without any fuss. It's a good landing spot at the end of a day around Oak Bluffs.
The patio at Sand Bar and Grille: umbrellas, high tops and red chairs on a sand floor beside the open bar.
Sand Bar at night, lit green and red, the deck still open after the sunset crowd has moved on.
After dinner, the ride back to Vineyard Haven is worth taking slowly. You get water views for much of the way, and it's a quiet end to the day.
Circuit Avenue is the town's main drag, with shops, cafes, and galleries packed along a walkable stretch. The Flying Horses Carousel, the oldest operating platform carousel in the United States, is here too, and worth a stop even without kids in tow.
Filmed July 2022The island moves on: shops, signs and prices may differ from what you see here. The text of this guide was checked October 2026.
Exploring the town? Start with our complete Oak Bluffs guide for food, beaches and parking.
Step 1 · WhenMonth PickerTwelve months compared on NOAA numbers, crowds, prices and what is open. 
Step 2 · DaysDay-by-Day Trip PlannerMorning, afternoon and evening sketched for every day, events dropped in, emailed to you. 
Step 3 · CostTrip Cost CalculatorFerry, beds with the rooms tax, meals, getting around and activities in one price range. 
The island's farmers markets, checked October 2026: the West Tisbury Farmers Market at the Agricultural Hall (Saturdays to October 31, 9 AM to noon), the Harvest Festival on October 24, the indoor winter market, Edgartown's summer Tuesday market, and the farm stands that stay open all year.
The Martha's Vineyard Songwriters Festival, September 17 to 20, 2026: a free kickoff at Nomans and three nights of Nashville writers at the Strand Theatre in Oak Bluffs, with our photographs from inside the Strand, the night-by-night lineups and practical notes for next year.
Where Martha's Vineyard's oysters, bay scallops and quahogs come from: the public solar hatchery on Lagoon Pond that turned fifty in 2026, the dozen oyster farms in Katama Bay, Menemsha Pond and Vineyard Sound, the wild beds in the great ponds, the autumn scallop season and its limits, visitor shellfish permits by town, why rain closes a pond, and where to eat them.
Lobster on Martha's Vineyard from trap to paper plate: how the small Menemsha fleet fishes, the Massachusetts rules on size, egg-bearing females and whale-safe gear, where to buy lobster off the boat (Larsen's, Menemsha Fish Market, The Net Result), how to eat it on the dock with your own bottle, and how a visitor can get a permit and catch a few.
The Feast of the Holy Ghost in Oak Bluffs, held every third full weekend of July since 1928: the Queen Isabel legend behind the free soup, the Sunday parade from the ferry up Circuit Avenue, the crown blessed at Our Lady Star of the Sea, the sopas at the Portuguese-American Club, the club the rest of the year, and how a visitor should behave at the island's Portuguese feast.
Every supermarket and market on Martha's Vineyard with posted hours: Stop and Shop, Cronig's, Reliable Market, Alley's, the meat and fish markets, the Falmouth Stop and Shop before the ferry, Instacart and pre-stocking delivery, and an honest word on island prices.
Island tip of the day Timing No. 61 of 79 New tip at midnight, island time
Visit Edgartown on a Tuesday or Wednesday. Same beautiful town, maybe 30% of the weekend crowds. Most restaurants have availability without reservations.
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