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Oak Bluffs Harbor at the end of the day, on video: the three waterfront restaurants (Jetty Beach House in the old Lobsterville Bar spot, Nancy's and Donovan's Reef, the Sand Bar and Grille), the marina, the ferries and the jetty, with the bus, the one-hour parking rule and East Chop Light for a quieter sunset.
Oak Bluffs Harbor is the one harbor on Martha’s Vineyard where you can eat dinner with your feet almost in the water and watch the day end over the boats. The town-owned marina fills with visiting boats from late May to about October 20, the seasonal ferries from Hyannis, Falmouth and New Bedford tie up at the pier beside it, and a row of restaurants and bars runs along the walkway above the slips. Three of them are right on the water: Jetty Beach House, Nancy’s Temporarily closed Closed for the season; reopening May 2027, per its own site and the Sand Bar and Grille. This page is the harbor at the end of the day, on video and in photographs, with what each place is and how to get here. The short clip below is golden hour over the harbor, the flag up and boats in the slips.
Filmed October 2026
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The harbor faces the Sound through a gap between two stone jetties, and the walkway along Lake Avenue and Circuit Avenue Extension looks west across the slips and the mooring field toward the Vineyard Haven side, where the sun goes down in summer. The video below was filmed from the waterfront rail at the old Lobsterville Bar and Grille on a summer evening: the light going gold on the water, the boats coming back in, the restaurant decks filling up. Dinghies putter through the moorings, the charter boats come back with their rods still up, and the big houses on the East Chop bluff catch the last light.
Filmed July 2022The island moves on: shops, signs and prices may differ from what you see here. The text of this guide was checked November 2026.
Oak Bluffs harbor at sunset in summer, the dinghies in and the big houses on the bluff lit by the last light.
Sunset over the water from a waterfront railing.
Two center-consoles back at the dock in Oak Bluffs harbor at sunset, rods and outriggers still up and a charter sign on one console.
The harbor just after sunset, the docks quiet and Nancy’s lit up across the water.
Lobsterville Bar and Grille sat directly on the water, and from a table there you could watch the sun go down over the harbor with a lobster roll and a drink. In 2026 the building reopened as Jetty Beach House, a raw bar, grill and cocktail place, so the view is still on the menu; the new sign hangs off the same building. Like most of the harbor front it is seasonal, so check its own site for opening dates before planning an evening around it.
Jetty Beach House, raw bar, grill and cocktails in the old Lobsterville spot, with its new sign hanging off the porch.
Oak Bluffs harbor on a summer night, the lights of the harbor front doubled in the water. The Hy-Line lands in this harbor, and the evening boat home leaves from it.
Dockside restaurants and crowds around Oak Bluffs harbor on a summer evening.
Nancy’s, at 29 Lake Avenue, has been family-owned on the harbor since 1960 and is the harbor front’s institution: a broad menu from seafood to burgers, a sushi bar, room for families and bigger groups, and the outdoor Donovan’s Reef bar, where the frozen Dirty Banana has a cult following and the upstairs deck has one of the island’s best angles on a sunset drink. The same family runs Nomans Temporarily closed Closed for the season; back in 2027, per its own site up the road. Nancy’s is seasonal and closes for the winter; its own site posts the spring opening date.
The second video was filmed from Nancy’s on a busy July afternoon in 2022, looking out over the marina: boats tied up, water moving, people out on the docks. It is the harbor at its liveliest, and a fair preview of a summer lunch here.
Filmed July 2022The island moves on: shops, signs and prices may differ from what you see here. The text of this guide was checked November 2026.
Nancy’s from the harbor boardwalk on a busy August day: the upstairs deck full, the shark over the door.
A bartender pouring two Dirty Bananas from the blender at Donovan's Reef, the outdoor bar at Nancy's.
A dinghy putters through a packed mooring field on a summer day.
The Sand Bar and Grille is the casual one: an open-air bar with red stools on the sand by the harbor, umbrellas up by day, string lights after dark, food and drinks without any fuss. It bills itself as the Vineyard’s only toes-in-the-sand beach bar, and an old painted Welcome to Oak Bluffs sign from the amusement-center days hangs on the wall inside. It is a good landing spot at the end of a day around town, a few steps from the Island Queen landing.
The Sand Bar and Grille patio on the harbor, umbrellas up and people at the bar and at the tables on the sand.
The Sand Bar and Grille after dark: an open-air bar with red stools, string lights and the floodlights on the pavers. The harbor is across the lane.
An old painted Welcome to Oak Bluffs sign, now on the wall inside the Sand Bar and Grille: hospitality, hotels and rooming facilities, beautiful parks, excellent bathing and beaches, good food and amusements.
The town-owned marina at 10 Circuit Avenue Extension rents slips and moorings to visiting boats each season through Dockwa; the posted 2024 rate was $4 to $5 per foot per night, and it runs from late May to about October 20. The sign at the harbor mouth gives arriving boats the channels: marina on 71, launch on 77. In summer the seasonal passenger ferries land at the pier here, the Hy-Line from Hyannis turning in past the jetty, the Island Queen from Falmouth and the Seastreak from New Bedford, and the Steamship from Woods Hole uses the Oak Bluffs slip from May to October; our ferry guide has the dates. The stone jetties are half fishing spot and half front-row bench for the boat traffic, with anglers set up at the end in the evening light. Bikes and little rental cars hire out from the same strip by the harbor, and the winter walk around the marina shows the same place with the slips bare. On the third Friday in August, in the years it runs, the town’s fireworks go up off Ocean Park, a short walk from the harbor; our fireworks guide has the details. Our video below is a quiet sunset from the boardwalk along the shore, with the beach below and boats out on the water.
Filmed August 2025
The harborside boardwalk at Oak Bluffs: benches along the rail, the breakwater rocks below, the pier beyond.
The Hy-Line fast boat Lady Martha turning in past the jetty at Oak Bluffs under a mackerel sky. The Hyannis run lands here, at the harbor, not at the Steamship pier.
Anglers set up at the end of a rock jetty in Oak Bluffs in the evening light.
The sign at the harbor mouth for anyone arriving by water: marina on channel 71, launch on channel 77, and the moorings beyond.
Cars and bikes rent from the same strip by the harbor: the Minis in the lot, the bikes lined up out front, and a small kiosk for the paperwork.
The gingerbread rooflines and umbrellas of the Oak Bluffs harbor front. Off the Island Queen and around the corner, this is the first thing you see, and the last drink before the 6:45 boat home.
The harbor walkway on a clear winter day, the benches empty and most of the slips bare.
The VTA Route 13 bus from Vineyard Haven and Edgartown stops at the Oak Bluffs ferry pier, steps from the harbor front, and all VTA rides are fare-free through June 30, 2027. Driving, Circuit Avenue parking is limited to one hour from 9 to 5 all year, and Ocean Park and the side streets are free where signed; the parking guide has the rest. For a quieter sunset without a menu, East Chop Lighthouse sits 79 feet up on the bluff about a mile and a half from Circuit Avenue, roughly 30 minutes on foot around the harbor and up East Chop Drive, facing west over Vineyard Haven Harbor; our sunset guide ranks every spot on the island. After dinner, the ride back to Vineyard Haven along Beach Road has water views most of the way. Circuit Avenue, the town’s main street, and the Flying Horses Carousel at 15 Lake Avenue, the oldest operating platform carousel in America, are a block inland.
Sunset from a road by the water, the sun going down past the shingled houses.
Bus 116 on Route 13, paused at the Oak Bluffs ferry stop with the pier out the window. It came from Edgartown along Beach Road and carries on to Vineyard Haven; the sign on the pole says Route 13 buses to Vineyard Haven load on this side of the street.
The three on the water, Jetty Beach House, Nancy’s (with the upstairs deck at Donovan’s Reef) and the Sand Bar, all look west across the harbor. Nancy’s deck has the height; the Sand Bar has the sand.
The waterfront places are seasonal and close in the fall. Our winter walk around the marina covers what was open last winter, and our year-round guide lists the Oak Bluffs restaurants that never close.
Yes. The walkway along the slips has benches facing the water, and the jetties are free to walk out on.
Around 8 PM in midsummer and before 4:30 PM from mid-November; our sunset guide has the month-by-month times.
How we checked: both videos and all photographs are ours, from the harbor front in 2022 and 2026. Restaurant histories and the Jetty Beach House change come from our Oak Bluffs town guide and restaurant guide (checked on the restaurants’ own sites and the island papers); marina rates and dates from the Oak Bluffs harbormaster’s posted information as cited in our winter marina walk; parking from the town’s posted signs; ferry dates from the operators. Last checked November 1, 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. From MV Vacation, written on Martha’s Vineyard · https://mvvacation.com/blog/oak-bluffs-lobsterville-bar-sunset · printed . Hours, prices and schedules change; the page online is the current one.
Oak Bluffs hotels and inns one by one, from the ferry pier to the Campground and the Inkwell: rooms, breakfast, parking, pets and season as each property states them, with rates by band and how to book for 2027.
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.
Island tip of the day Ferry No. 2 of 79 New tip at midnight, island time
Walk-on passengers never need a reservation on SSA ferries. $11 one-way: buy at the terminal or via the SSA eFerry mobile site. On peak summer weekends, arrive 30 minutes early to guarantee your seat.
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