The last Steamship Authority boats called at Oak Bluffs on October 22. Under the winter schedule that began October 23, every boat from Woods Hole lands in Vineyard Haven, and it stays that way through January 5, 2027. That puts this year's crop of Circuit Avenue openings into their first off-season with no ferry line outside the door. A few of them were planned for these months from the start.
The Front Door Moves Down the Road
Most fall boats were already landing in Vineyard Haven well before the terminal closed. The fall schedule began September 11, and from then until October 22 only four daily round trips still stopped at Oak Bluffs. The Oak Bluffs dock is seasonal and runs roughly mid-May to late October. In the deep off-season, every boat uses the Vineyard Haven terminal.
Without ferry foot traffic, Circuit Avenue depends on people who come by car or bus. The Martha's Vineyard Transit Authority fall schedule took effect October 4. It covers Oak Bluffs on routes #7, #9 and #13, and Route #11 is marked "Done for the season." Buses stay fare-free through June 30, 2027, and they run every day of the year except Thanksgiving and Christmas Day.
A Breakfast Counter Named for East Chop
The clearest example of a business built for this season is Highlands General, which opened in the former Linda Jean's space. According to the Vineyard Gazette, the storefront had been dark for more than a year before it reopened this spring as a year-round fast-casual restaurant and market built around affordable comfort food.
The owners already run seasonal restaurants in town. The Gazette reported that Doug Abdelnour, who owns Nancy's and Nomans, bought the building with Vineyard hotelier Charles Hajjar for $4.9 million. They share the venture with Nancy's managers Steve Ansara and Kelly Sciandra, and Sciandra also owns Aalia's. Nancy's wound down in mid-to-late September. So the same group now has a seasonal harborfront restaurant closed for the winter and a Circuit Avenue counter that stays open.
Abdelnour explained the reasoning to the Gazette:
"It was obvious that Oak Bluffs needed another breakfast spot where you could actually come in, order, sit down if you want [or] take it to go if you want."
The name has a local story. Abdelnour told the Gazette that "Highlands" refers to the historic Highlands neighborhood of Oak Bluffs, now called East Chop. The logo shows the tabernacle that once anchored that area. He described the old Highlands block parties, where people went house to house sharing food, and said, "I love the thought of that." The Highlands General website lists it as a year-round coffee, breakfast and lunch spot, open daily from 7 a.m. to 5 p.m., with online ordering. In April, the MV Times listed hours of 7 a.m. to 4 p.m., with longer hours in peak season. Hours have already changed once since opening, so the website is the place to check before a weekday morning visit.
Coffee and Cocktails, Through December If Plans Hold
A few doors down, the Black Dog moved into Oak Bluffs this summer. In May, the Vineyard Gazette reported that the select board had approved a full-service restaurant at 6 Circuit Avenue, the former Mikado space. At the time it was called Coastwise Pub. Dan Pucillo, the Black Dog Tavern's CEO and president, described the idea in five words: "Coffee and cocktails is our concept."
The off-season detail from that meeting is the date. Pucillo told the board the pub would not stay open late, would keep noise low, and that he hoped to stay open through Dec. 31 for the winter holidays. That was a goal, not an announced schedule. The Black Dog Pub's own page currently lists 6 Circuit Ave, downstairs, open daily 7 a.m. to 10 p.m. Breakfast runs 7 to 11 a.m., lunch noon to 4 p.m., and dinner 4 to 8 p.m. The kitchen serves until 8 p.m. Sunday through Thursday and until 9 p.m. Friday and Saturday.
Highlands General and the Black Dog Pub both serve morning coffee and early breakfast. That is the part of the day ferry traffic used to fill and the part year-round residents use all winter.
The Anchors That Already Know the Winter
The newcomers join a few Circuit Avenue businesses with long off-season track records. The Offshore Ale Company calls itself the island's only year-round brewpub. It serves lunch and dinner daily, 11:30 a.m. to 9:30 p.m. Sunday through Thursday and until 10 p.m. Friday and Saturday, and the bar stays open late every night. Its fireplace and wood floors make it a long-running January stop.
The Ritz has been on Circuit Avenue since 1944 and has kept weekend live music going through past winters. The Ritz show calendar points visitors to its social media for live updates, and that is where its November lineup will appear.
Esh, at 50 Circuit Avenue, was rebranded from Dos Mas in March around a restored fireplace, with a California chef cooking progressive American food. Its website lists more than one set of hours, so a call ahead is the reliable way to plan dinner there this fall. Jetty Beach House, at 8 Circuit Ave Ext., opened Memorial Day weekend as a seasonal harborside restaurant.
The Calendar From Halloween Into December
The town's own calendar fills the late-fall weekends. Most of the dates below come from the Oak Bluffs Council on Aging, the Oak Bluffs Association and the Oak Bluffs Library's November calendar.
- Thursday, October 29, 1 p.m. Council on Aging Halloween pizza party. Reservations required, according to the Council's October calendar in the MV Times.
- Saturday, October 31, all day. Halloween in Oak Bluffs, organized by the Oak Bluffs Association. The town calendar listing names Sofie Green as the contact. The association's page is a save-the-date for now, without 2026 hours or a route.
- Wednesdays through November 25, 8:15 to 10 a.m. Old-Time Appalachian Jam at the library. The November 11 session is canceled.
- Saturday, November 14, 11 a.m. to 12:30 p.m. "Truth and Tea: Wôpanâak Foodways and the Truth About Thanksgiving" at the library.
- Saturday, November 28, 10:30 a.m. to noon. A cranberry celebration at the library.
- Through December 7. SHINE and Open Enrollment appointments through the Council on Aging, which also runs weekly exercise, volleyball, knitting and crochet, bingo, and senior bowling that started September 29.
The library's two November food programs both look at the island's own harvest. The November 14 program focuses on Wôpanâak foodways. The November 28 program, two days after Thanksgiving, celebrates cranberries.
The Highlands Road Still Waiting
The name on the new breakfast counter points back to East Chop, the neighborhood behind the town's largest unfinished project. The East Chop Drive Coastal Restoration would rebuild more than 2,000 feet of eroding bluff. According to the MV Times, parts of the road have been fully closed for nearly 15 years, and the road is often closed during storms.
The funding history explains the delay. The town first applied to FEMA in 2013, after Hurricane Sandy. FEMA awarded $10 million in 2022, alongside a $3 million state grant and $6.9 million approved by the town. As of spring 2025, permitting delays and rising costs had pushed the total to $33.3 million, and the town was $16.39 million short. This year the eligibility window for the federal money ran out in May. FEMA denied the town's request for a 22-month extension, and the $10 million was rescinded.
Town administrator Wendy Brough told the MV Times that the project's scope and the town's commitment have not changed. The town is waiting for final approval from the U.S. Army Corps of Engineers, which she said would make future grant applications more competitive. As of the paper's October 7 report, the town was preparing an application to the Federal Highway Administration's PROTECT program, with a companion application to the state. Brough said the town may also apply to FEMA's BRIC program again when applications open in the new year. No construction start date has been set. Over the winter, the next milestones are the Army Corps decision and the PROTECT application.
The ferry is due back at the Oak Bluffs terminal in late spring. Until then, Circuit Avenue's year-round businesses and the town's own calendar carry downtown Oak Bluffs.
If your Oak Bluffs home is closing up for the winter, or you're thinking about keeping it open for off-season stays, Susan Anson can help with winter turnovers, seasonal rental planning and the details that come with owning on the island year-round. Request a private consultation.
