"There's a big disconnect on the Island between what businesses can produce and what real estate is worth," Erin Tiernan told the Vineyard Gazette in late September. She was explaining why Basics Clothing Company, the family outfitter at 24 Circuit Avenue, will close for good in December.
Basics has been one of the few shops on Circuit Avenue that stays open year-round. When it goes, the reason won't be slow sales or a bad summer. The owner of its building, the Barmakian Realty Trust, showed interest in selling. Tiernan and her partners, Thomas and Laurel Welch, decided a new owner meant too much uncertainty.
That pattern explains most of downtown Oak Bluffs this fall. The year-round places that are new, the ones that have moved, and the one that's leaving all trace back to a property changing hands. Each building sale reshaped part of the off-season map.
The building above Basics
The Gazette's account shows how a building sale reaches a storefront. Tiernan lives in a condo above Basics. She told the paper that if someone else bought the building, their higher mortgage payment would push the rent past what the shop could support.
The building also houses The Corner Store. It's assessed at more than $3 million, and the Gazette reported that no public listing had been posted.
The closing affects more than one shop. Tiernan also runs Oso and co-owns Eastaway, Basics' seasonal sister store at 20 Circuit Avenue, with the Welches. She said that "without Basics, the corporation really doesn't support all three of us." One partner will keep Eastaway going, but they hadn't settled which one when the story ran. Tiernan has worked at Basics for 23 years and has been a part-owner for 17.
For anyone who buys school clothes, work layers or a last-minute gift downtown in February, December is the deadline.
The new year-round rooms all started as property changes
The same forces brought new places to Circuit Avenue this year, and three of them matter most for the off-season.
Highlands General, 25 Circuit Avenue. This is the old Linda Jean's spot. The MV Times reported in June that restaurateur Michael Santoro had planned a restaurant called Michael's for the space, but those plans fell through and Highlands General moved in. Doug Abdelnour, Charles Hajjar, Steve Ansara and Kelly Sciandra run it as a counter-service café and market. Its website calls it a year-round spot for coffee, breakfast and lunch, open daily from 7 a.m. to 5 p.m. The MV Times listed 7 a.m. to 4 p.m. when it reviewed the café in April, so check the hours before a late-afternoon run.
The Black Dog Pub, 6 Circuit Avenue. This is the former Oak Bluffs Mikado space. It was announced as Coastwise Pub when the Oak Bluffs select board approved it in May. CEO Dan Pucillo described a "coffee and cocktails" concept serving breakfast, lunch and dinner. He also said it wouldn't stay open late and would keep the noise down. The Black Dog's own page now lists the pub at that address, open daily from 7 a.m. to 10 p.m. For winter, Pucillo said he hopes to stay open through Dec. 31 for the holidays. That's a hope, not a posted schedule.
Martha's Vineyard Chowder Company, 14 Kennebec Avenue. Owner JB Blau moved the restaurant off Oak Bluffs Avenue into the remodeled space that once held Red Cat Kitchen and Zapotec. He announced a smaller operation that would put less weight on nightlife. "As we move closer to retirement, we want to focus on a more manageable, high-quality experience rather than a high-volume club atmosphere," he wrote. Island attorney Geoghan Coogan described the new spot to the select board: "No entertainment, just residences above it." The restaurant's website lists seven-day service, 11 a.m. to 9:30 p.m. Sunday through Thursday and until 10 p.m. Friday and Saturday. It doesn't say whether those hours hold through winter.
Here's the downtown lineup as of late September, using what each source actually says:
| Address | Previously | Now | Off-season status in the sources |
|---|---|---|---|
| 25 Circuit Ave. | Linda Jean's | Highlands General | Calls itself year-round |
| 6 Circuit Ave. | Mikado | The Black Dog Pub | Owner hopes to stay open through Dec. 31 |
| 14 Kennebec Ave. | Red Cat Kitchen | MV Chowder Company | Open seven days; winter hours not stated |
| Circuit Ave. | Dos Mas | Esh | Open in late September |
| 24 Circuit Ave. | Basics | Basics | Closing in December |
Esh is the Shai family's renamed restaurant. Evan, Zared and Megan Shai turned the Mexican Dos Mas into an upscale American room this spring. It was on the open list in a year-round restaurant tracker updated Sept. 30. The tracker also listed Biscuits, Coop de Ville, Nomans, Offshore Ale and Mad Martha's as open. That's a snapshot of late September, not a promise about January.
The waterfront rooms already went dark
The two splashiest openings of 2026 were the first to close for the season.
The old Chowder Company space on Oak Bluffs Avenue was approved in April as Inkwell Beach House. AJ Calloway is leading the venture, and chef G. Garvin is running the kitchen. In June it became Inkwell Beach Club after a trademark lawsuit, since a nearby hotel uses the older name. In April, Calloway said he hoped to hold events year-round. By Sept. 30, the tracker listed Inkwell Beach Club as closed for the season.
Jetty Beach House replaced Lobsterville Bar & Grille at 8 Circuit Avenue Extension. Jordan Wallace of Midnight Taco runs it with partner Mike Tierney. It opened Memorial Day weekend as a seasonal restaurant. It was still on the open list at the end of September, and none of the reporting gives a closing date. Wallace told the MV Times the plan was to serve wine and local seafood and to give artists and musicians a place to gather "throughout the summer."
These businesses were planned for summer. The places that stay open into winter are the ones on Circuit and Kennebec with modest rooms, early hours, and in Chowder Company's case, apartments upstairs.
30 Circuit Avenue, where housing goes upstairs
The longest-term change on the street is at the old Phillips Hardware. The store was open for nearly a century before owners Donna Leon and Susan Phillips retired and closed it in 2025. The MV Times reported in June that the building had been torn down.
Jennifer Freeman Pacheco owns the lot through 30 Circuit LLC, which also owns Reliable Market next door. She proposed a three-story, Victorian-style building with two ground-floor retail spaces and 10 apartments for year-round employees. According to the application, the shops would sell dry goods. Leon and Phillips got approval for a version of the plan back in 2016, but it was never built. The Martha's Vineyard Commission's preservation consultant estimated that the original building dated to the mid-1870s. The commission lists the project, Oakwood Mixed Use, as approved on April 9, 2026. In January, the applicant's first plan was to have demolition and the rebuild largely finished by April. Some commission staff and commissioners called that timeline unrealistic. No updated completion date has been reported since.
The Phillips lot and the Basics building are two ends of the same story. At 24 Circuit, a possible sale threatens a year-round shop and the apartment above it. At 30 Circuit, a new owner is building shops downstairs and year-round apartments upstairs. The MV Times story on Oak Bluffs turnover also noted that Benito's Hair Styling moved to Edgartown last November after its building was sold.
What's on the October calendar downtown
Fall still has plenty going on downtown, as long as you go by the dates:
- Ocean Park Sunday music continues through October on its fall schedule, 5 to 7 p.m. That's half an hour earlier than the 5:30 to 7:30 p.m. summer slot.
- Back Door Donuts has its back-door window open from 7 to 11 p.m., Wednesday through Sunday, and its front bakery open 8 a.m. to 2 p.m. on Monday and Thursday through Sunday. The late-night window closes sometime in late October, and there's no exact date.
- Nomans, 15 Island Inn Road, is holding its first cornhole tournament on Saturday, Oct. 10, from noon to 4 p.m. Teams of two pay $50, and proceeds go to sick and injured local firefighters.
- Offshore Ale is listed in fall guides as one of Oak Bluffs' year-round anchors.
After that, the winter map comes down to a few addresses: Highlands General in the morning, the Black Dog Pub at least through New Year's Eve if Pucillo's plan holds, Chowder Company on Kennebec Avenue, and Basics until December.
Many of these changes began with a building changing hands. At Donnelly + Co, we follow those sales closely because they shape the street residents live on. If you own downtown property in Oak Bluffs, or you're wondering what a sale on your block could mean, we're happy to talk it through.
