West Tisbury, where up-Island begins, is a mix of village and country with three distinct, if not always designated, business areas — one of which is older than the town itself.

This photo of a young Henry Beetle Hough on his horse in front of the West Tisbury post office shows what the building that now houses clothing boutique June looked like in 1908. Vineyard Gazette Archives

The best-known and most photogenic of the three, at the beginning of South road, is home to West Tisbury’s library, town offices and senior center, along with Alley’s General Store, 7A Foods, the Field Gallery, Up Island Automotive, Mid-Island Repair, and the Grange Hall, where the West Tisbury Farmers’ Market and other community events draw crowds.

Farther north on State road, in the North Tisbury commercial district, a cluster of year-round businesses includes up-Island Cronig’s Market, Conroy Apothecary, Fella’s Take Out, a U.S. Post Office and a few office and professional buildings. The Vineyard Gardens nursery, Martha’s Vineyard Public Charter School and West Tisbury fire station are there as well.

In between these two centers of activity is a stretch along State road, historically known as Middletown, that was already engaged in commerce before the original town of Tisbury was founded in 1671.

Jared Maciel

On their long journey to the hills and cliffs of the Vineyard’s western region, early travelers from down-Island could have their horses watered, rested and shod in Middletown before heading onto North road, according to Vineyard Gazette archives. Cabinet makers and weavers also plied their trade there.

As years went by, towns, a county and a state — within a new nation — rose around Middletown, but it remained a mixed settlement of businesses and rural residences, some alongside roads that remain unpaved today.

Today the area retains its country character with farms and horses behind old stone walls and split-rail fences. Middletown never achieved zoning status as a commercial district of West Tisbury, and its mercantile side has waned and waxed over the centuries.

Now the area is home to State Road restaurant, Middletown Nursery, North Tisbury Farm & Market, Martha's Vineyard Glassworks, MM Antiques and the new boutique June, all located along State Road.

Nearly half these locations had been vacant for years before their current occupants opened up shop, making Middletown an up-Island destination where it was once a way station.

Coming from the South, you know you’re entering Middletown when you see the neighborhood’s oldest resident, a white oak tree — thought to be some 300 years old — standing alone in a privately-owned field just past the intersection where North road joins State road.

Don't miss the neighborhood’s oldest resident, a white oak tree. Jeanna Shepard

Made famous by a 1968 Alfred Eisenstaedt photograph, the stately oak has aged visibly since its heyday. Its lower limbs now touch the ground. But the owners of the land have been giving it professional tree care, and Polly Hill Arboretum executive director Tim Boland told the Gazette in 2016 that it could have another century of life.

Just past the tree and on the same side of State road, you’ll come to June, a new clothing store for women.

“The focus is on sustainably and ethically made clothing and basic, good everyday wear,” said Gina Solon, who opened her boutique last month in the historic former West Tisbury post office that had long housed the Bananas boutique and gallery. Upstairs, Island artisans Elizabeth Cecil and Nettie Kent share studio space.

Gina has selected pieces from small, mostly woman-owned brands, many by independent West Coast designers. She also sells jewelry, fairly traded Mexican hand-woven cotton throws and bags, letterpress cards and jar candles with names like Adulting (“Smells like early nights and steady paychecks/Fig & Cashmere”). The shop is open from 10 a.m. to 6 p.m. every day during the summer.

In between the tree and June, unpaved Rogers path leads to Middletown’s old cemetery. Tucked into the woods where the loudest sounds are birdsongs and the wind in the trees, the North Tisbury Burial Ground was established in 1809, more than 80 years before West Tisbury separated itself from the town of Tisbury. Its headstones bear the names of Island people who lived and died — some lost at sea — in the 19th century, a few of them born in the late 1700s.

Rogers Path leads past the old North Tisbury cemetery. Jeanna Shepard

Back up the path and across State road, State Road restaurant is now open nightly for dinner from 5:30 to 9:30 p.m. and Sundays for brunch from 8 a.m. to 2 p.m. Mary and Jackson Kenworth — who also own Beach Road restaurant in Vineyard Haven — opened State Road in 2009 in the former Deon’s, which had stood unoccupied after a 2007 fire. Previous restaurants on the site include Bittersweet and the original Red Cat.

The Kenworths’ comfortable eatery serves American cuisine with a distinct Vineyard accent, sourcing as much as possible from Island farms, fisheries and food producers — including the restaurant’s own garden.

Staff baker Leslie Hewson turns out breads made with Island grains and brunch treats including the incredible Limpopo – something like a brioche jelly donut, minus jelly – the supersized Texas Sticky Bun and the Golden Burst, a buttery explosion of brioche and caramelized fruit.

Paired with a latté, one of these makes a fine breakfast to go, but if you have the time, grab a table and do some people-watching while you enjoy an Island egg sandwich, mushroom toast, codfish cakes with fried eggs or anything else on the menu that catches your fancy.

Continuing, well-fed, along State road, you can’t miss Middletown Nursery, a garden center bursting with plants that almost conceal a gift shop bulging with inspirations. Like the restaurant, the nursery had been vacant – in this case for five years – before its current owners, John and Heather Hoff, revived it in 2008. Today, Middletown Nursery bustles from springtime through Christmas with annuals, shrubs and flowering perennials, including David Austin roses, for home gardeners and landscapers. The annual selection also includes their own Island-grown seedlings for your vegetable garden.

Middletown Nursery has a large selection of perennials and annuals as well as a gift and florist shop. Jeanna Shepard

Strolling the grounds, you’ll find plants for sun behind the shop and an airy, spacious lath house for shade plants closer to the road, where a rustic bridge leads over a water lily pond to the sidewalk. The shop is packed with colorful gifts and cards for gardeners and non-gardeners alike. There’s even a florist’s counter, with a cold case filled with blooms. Middletown Nursery is open from 9 a.m. to 5 p.m. Monday through Saturday and 10 a.m. to 4 p.m. on Sunday.

North Tisbury Farm and Market occupies the space that was once Farmer Greene's farm stand and later Fiddlehead Farm. Jeanna Shepard

Across the street, MV Glassworks is a sunny, family-owned gallery and workshop turning out fine art glass creations as you watch the artisans working at the fiery kilns. Smoke damage from a small fire in the cellar forced the studio to close in February, but it is open again from 10 a.m. to 4 p.m. Thursday through Sunday.

Continuing north on State road, keep your eye out on the left for MM Antiques — open by appointment and chance — and on the right for North Tisbury Farm & Market, a roadside farm stand and grocery store that was known as Fiddlehead Farm until it closed in 2016. The property belongs to the family of Island farmer Donald Mills who ran it as Hillside Farm and died in 2014.

Before Donnie took over the farm in 1974, Farmer Louis M. Greene had worked the land since 1938. “Farmer Greene” was known for his vegetables. He had inherited the land in 1915 from his father. Last year, business owner Rose Willett reopened the farm stand, which sells produce raised on the property from seeds started in an old greenhouse out back. If you don’t see what you’re looking for at the farm stand, ask and you could receive it freshly cut for you from the field outside.

North Tisbury Farm & Market also sells cold drinks, hot and cold-brewed coffees, snacks, meats and cheeses and boutique groceries including an array of ethnic foods. They also carry bread from Falmouth’s French bakery, Maison Villatte. The farm stand is open from 8 a.m. to 6 p.m. Monday through Saturday and from 9 a.m. to 5 p.m. on Sunday.

Spend some time in Middletown, and you may decide it’s your favorite Island “town” of all.


Louisa Hufstader lives in Edgartown but has been known to venture up-Island on occasion.