Walk down Circuit Avenue this month and the storefronts read like a rewritten roster. Three restaurants opened or rebranded before Memorial Day, a fourth just got its select board approval, and a fifth is being staged for later this summer. In the same eight weeks, the carousel at the top of the street turns 150 and the swim club at Inkwell Beach opens its 80th season. Oak Bluffs is doing two things at once right now, and if you live here, both are worth paying attention to.
The Circuit Avenue Reset
For the last few summers, the restaurant conversation in town has been about who was closing. This year it flipped. The 2026 summer scene is less about brand new than about reinvention, and the activity is concentrated in Vineyard Haven and Oak Bluffs, but the pace of turnover on the Oak Bluffs side is where the story lives.
Start at 8 Circuit Avenue Extension. Jetty Beach House opened Memorial Day weekend in the former Lobsterville Bar and Grille space, as a joint venture from Jordan Wallace, owner of Midnight Taco and Midnight Mediterranean, and Mike Tierney, a co-owner of Washashore Laundromat. The menu runs from Baja fish tacos and hot lobster rolls to whole fried black bass and spicy mussels, with a new marble bar, a raw bar, and live music turning the room over from lunch to evening.
A block away, the old Linda Jean's diner has a new identity. It reopened in late March 2026 as Highlands General, a year-round fast-casual restaurant and market run by a group that includes Nomans owner Doug Abdelnour, hotelier Charles Hajjar, and the managers of Nancy's, open daily 7:00 AM to 5:00 PM, which makes it one of the few reliable year-round breakfast options in town. The year-round part matters more than the menu. For anyone here past October, a real breakfast on Circuit Avenue in February has been a rumor for a decade.
At 6 Circuit Avenue, the Mikado space is next. Coastwise Pub, a full-service restaurant from the Black Dog, will move into the space formerly occupied by Asian fusion restaurant Mikado this summer after being approved by the Oak Bluffs select board, offering full-service breakfast, lunch and dinner on the town's main commercial drag. Unlike prior Black Dog concepts where drinks played second to food, Coastwise will lean into a cocktail bar atmosphere, with a menu designed to reflect the Oak Bluffs summer while keeping a few Tavern favorites.
The Chowder Company didn't disappear so much as compress. Martha's Vineyard Chowder Co. reopened this spring in a smaller but fully renovated space at 14 Kennebec Avenue, with the same favorites on the menu, including their 2025 "Best of the Vineyard" clam chowder. Its old Oak Bluffs Avenue address is already spoken for. Inkwell Beach House is set to fill the former Martha's Vineyard Chowder Company space on Oak Bluffs Avenue after being approved by the select board, in a venture spearheaded by television personality and summer Islander AJ Calloway. Downstairs will be a restaurant manned by celebrity chef G. Garvin, who hosts several cooking shows including Turn Up the Heat with G. Garvin and Hustle, Sizzle, and Smoke, with upstairs suited to conversation groups, art, and music performances.
Two more shifts worth knowing: Esh on Circuit Avenue rebranded from Dos Mas in March 2026, calling itself "progressive American" with a new California chef, pivoting from Mexican to a broader seasonal American approach, and up at 15 Island Inn Road, Nomans, the seasonal counter-service spot with lawn games and live music that took over the old Lola's space, opened its seventh season on May 14, 2026 and runs a free shuttle from the harbor in summer.
Read together, that is six meaningful changes in one commercial district in a single season. Here is the shuffle in one view:
| Address | Former Tenant | Now |
|---|---|---|
| 8 Circuit Ave Ext | Lobsterville Bar & Grille | Jetty Beach House |
| Circuit Ave (Linda Jean's) | Linda Jean's | Highlands General |
| 6 Circuit Ave | Mikado | Coastwise Pub (opening) |
| Oak Bluffs Ave | MV Chowder Co. | Inkwell Beach House (opening) |
| 14 Kennebec Ave | (relocated MV Chowder Co.) | MV Chowder Co. |
| Circuit Ave | Dos Mas | Esh |
| 15 Island Inn Rd | Lola's | Nomans (year 7) |
If you keep a mental map of Circuit Avenue by "which door has which sign," the map is out of date.
What August Actually Looks Like
The event calendar for the next four weeks is dense enough that residents tend to pick their nights and let the rest pass. The anchors worth knowing:
- The 8-day summer festival showcasing R&B, soul, comedy, nightlife, and cultural experiences across the Island pairs with the Ag Fair and the African American Film Festival, both of which have moved to the second week of August. The Martha's Vineyard Agricultural Society Fair, the oldest continuous agricultural fair in the United States, runs Thursday through Sunday, August 13–16, marking the fair's permanent move to that week.
- The Possible Dreams Auction returns for its 48th year on Saturday, August 8, from 3 to 6:30 PM, hosted by Seth Meyers at Allen Farm in Chilmark, a working sheep farm with sweeping views of the Vineyard Sound, with proceeds benefiting Martha's Vineyard Community Services.
- Featherstone Musical Mondays run Mondays from late June through August at Featherstone in Oak Bluffs, doors around 6:30 PM, 6 PM in August, tickets $20.
- MVCMA Tabernacle Community Sings, a cherished Campground tradition, run Wednesday evenings from early July at the Oak Bluffs Tabernacle, with the MVCMA Sunset Concert Series on Friday evenings in July.
- "Sundays in the Park" free concerts run weekly at Ocean Park from late May through Columbus Day weekend, 5:30–7:30 PM through September and 5:00–7:00 PM in October, alternating between the Oak Bluffs and Vineyard Haven town bands.
- Illumination Night still lights up Oak Bluffs, and the Oak Bluffs Fireworks remain a highlight drawing crowds downtown.
The compression matters. Anyone with a spare bedroom knows the second week of August is now the point of maximum guest traffic, with the Ag Fair and the African American Film Festival in the same seven days. If you were used to spreading houseguests across two different weeks, that structure is gone.
Two Anniversaries Worth Walking To
Reinvention gets the headlines. Persistence deserves the walk.
The Flying Horses is a National Historic Landmark, designated in 1986 and operated by the Martha's Vineyard Preservation Trust. Rides cost $5 each, which goes toward keeping the machine running. 2026 is a milestone season: the Flying Horses turns 150 years old, and the Preservation Trust is marking it with an all-day birthday party on July 25. A carousel older than the Statue of Liberty spent its first century as a summer amusement and its second as a preservation project. The brass ring is still real brass.
Down at the beach, the Polar Bears of Martha's Vineyard, a morning swim group founded by Black women in 1946, still gather at the Inkwell every morning from July 4 through Labor Day at 7:30 AM, with 2026 marking the group's 80th summer in the water. The gathering is free, open, and older than most of the porches on Ocean Park. If you have never walked down at 7:20 AM with a coffee, this is the summer to try it.
East Chop, When The Rest Of Town Is Loud
The counterweight to Circuit Avenue on a Sunday night has always been Telegraph Hill. The current 40-foot cast-iron tower at East Chop Lighthouse dates to 1878, and the Martha's Vineyard Museum opens it to the public on Sunday evenings around sunset in season, typically 7:00–9:00 PM in June and July, shifting to 6:00–8:00 PM in August. Confirm the exact dates through the museum before you go, because the schedule tightens as the days shorten. If you want a quiet 45 minutes with a view that is not on a menu anywhere, that is where it is.
Reading The Season
The through line: a town that has spent the last few summers absorbing losses is spending this one absorbing new operators, new anniversaries, and a compressed event calendar. Six restaurant changes in one district is not a coincidence, and the fact that year-round hours are part of two of them, Highlands General on Circuit and Chowder Co. on Kennebec, is the quieter story. Circuit Avenue in February has been dark for a long time. The 7 AM lights at Highlands are the first sign that the shoulder seasons might get their own economy back.
If you own a house here, you already knew the summer was going to be full. The version of Oak Bluffs your guests see this August is not the version they saw two summers ago, and telling them where to eat is a longer conversation than it used to be.
If you are weighing what to do with your Oak Bluffs home this season, whether that is opening it up for a rental week during the second-week-of-August compression, refreshing a kitchen before the fall market, or quietly testing the sale conversation, Anson Realty works with owners on all three. Request a private consultation.
