A 5-stop Martha's Vineyard food tour that tells the history of The Vineyard, bite by bite.
From a Wampanoag bakery to Ro-Ro Chili: the Island story in 5 delicious stops
I avoid history lectures like the plague. I blame it on high school history class, where memorizing the dates of wars around the world guaranteed an A on the final exam. Even at age 16, I knew I a) hated wars and b) memorizing dates is a drag and c) I was missing something important about the past.
Recently my friend Sue asked me to attend a history lecture about Martha’s Vineyard. Well, I thought, I’m better than my high school self and maybe it could be interesting and if wasn’t, well, we could bolt the lecture and go out to dinner.
A History Lesson Worth Staying For
It turns out that Bow Van Riper, the research librarian at the Martha’s Vineyard Museum, had me at hello. He doesn’t do dates and battles. He tells stories. Thematic ones.
With a sly sense of humor and a wealth of knowledge, Bow weaves a tale of faith, art and community throughout Martha’s Vineyard history. Taking notes as he spoke (I might have hated history class, but I was always a good student), I kept whispering to myself: “oh that’s why the island attracts so many artsy people” and “oh that’s why there are so many churches in Vineyard Haven”.
Being food obsessive, I also started thinking about how food connects the dots between today and yesterday’s life on the island.
All of which led me to this: a five-stop food tour (+one bonus extra stop) that traces the island’s history, one delicious bite-by-the-next.
1. Orange Peel Bakery: Wampanoag Spirit in Every Slice
Location: Aquinnah | Best for: Pizza nights, bread, community, the spirit of Wampanoag Indians past and present.
The Wampanoag people lived on this island for thousands of years before the British came. Their legacy lives on in the earth and at Julie Vanderhoop’s Orange Peel Bakery.
Julie is a Wampanoag tribal elder and a member of her town’s Board of Selectmen. Her feet are firmly planted in these two cultures and her bakery embodies that melding.
The Wampanoag lived off the land and the sea and with values that privileged respect and community. As Julie says, “it is community that will feed your soul.”
Step foot on the property and you can feel these values at work. A huge outdoor stone oven welcomes you with the scent of a campfire. Julie bakes pizza in the oven on Wednesday nights in the summer. Bring some beer, pull up a chair, eat communally or take the pizza home. Whatever you decide, it’s some of the best pizza you will ever eat.
Julie’s breads and pies had me oohing and aching. The bakery runs on the honor system; another way for her to bring to life the Wampanoag spirit of building strong community based on trust and caring for your fellow being.
“I can honestly say this place has made me a better person. It is so spiritual as well as healing for me to be on my territorial grounds, and to exemplify who I am and who my people are. Julie Vanderhoop in the MV Times.
In my mind, these Wampanoag values are the foundation of this island’s extraordinary community spirit.
2. Grace Episcopal Church on Friday nights: Lobster Rolls and Faith
Location: Vineyard Haven | Best for: Lobster rolls, chowder, old-school community
Churches, lots and lots of churches, anchored the various villages on Martha’s Vineyard throughout the 18th and 19th centuries.
John Sanders, an ex-slave turned pastor, brought the Methodist religion and its firebrand commitment to community and social justice to Martha’s Vineyard in the late 1700s.
Vineyard Haven, formerly known as Holmes Hole, was the working center of the island because it was - and is - the most accessible port on the island. Its large population attracted churches. The churches competed for parishioners and according to Bow, the Methodists, led by Sanders’ example, were the undisputed winners of the Church ratings game. They were the Elvis Presleys of their day - passionate, energetic, committed to community. Townspeople flocked to the churches to hear the Methodist preachers. The Congregationalists and Baptists? Not so much. They were the Pat Boones of their time: quiet rule-followers, pious without the pizzazz.
Fast forward: today, you can taste the legacy of churches as community centers every Friday night at the Grace Episcopal Church. Come for what many call the best lobster rolls on the island, chat with neighbors and enjoy the friendly vibe.
You’ll also find chowder, pie and hot dogs, served by volunteers and steeped in community spirit. Order online here, walk up on Friday night, or call 508-693-0332 by Thursday.
3. Farmers’ Market at Ag Hall: The heart of island agriculture every Wednesday and Saturday
Location: West Tisbury | Best for: Fresh produce, heritage, and that sheep-meets-sea feeling.
While the island lacks the convenience of Trader Joe’s and Whole Foods and Starbucks (to name my personal favorites), it overflows with farms that can be traced back, well, forever.
Farming and fishing were – and continue to be – the guts of the island. Whaling, too, but all that’s left of the whaling days are the stately homes the sea captains built.
Allen Farm, established in the late 1700s at the same time the Methodists were doing their thing, is the oldest, continually operating farm on the island. Jonathan Allen purchased land and built a farmhouse in 1770. The house is still standing. Records about who he purchased the land from and for how much are very sketchy, so you’ll have to imagine what that land deal might have been like. Today, sheep roam the property and the shop sells beautiful woolens.
In the mid-1800s, the Allens banded together with other local farms to create the Agricultural Society, because:
“….the attainment and diffusion of scientific and practical knowledge in the cultivation of the soil, is a subject of such importance as to demand the associated effort of the farmers of Dukes County.”
— Henry L Whiting, 1865 report Whiting, 1865 Report
The Society built Agricultural Hall, an important site in the middle of the island. If you want to get a taste of all that the Vineyard produces from land and sea, visit the Wednesday and Saturday Farmers’ Markets at the Agricultural Hall in West Tisbury.
All the farms are there.
For a special treat, check out the scallops from the Martha Rose, a local scallop fishing boat. They are, IMHO, the best in the whole entire world.
4. Chili on the ferry: Comfort in a Cup.
Love ‘em and hate ‘em, the ferries were - and are - a critical part of island life, both the life-blood and life-line.
In the 18th and 19th centuries, the waterways around the island were teaming, the boat traffic comparable to Route 95 around Boston at rush hour. The ports, and especially Vineyard Haven (Holmes Hole) were truck stops for the crews.
In 1817, coal-burning, steam wheel-churching passenger boats arrived. These boats brought summer people and summer people brought money. With the summer people came the desire to build resorts. Oak Bluffs is the only MV town built to be a resort. which was the stimulus behind building Oak Bluffs, the only MV town built as a summer playground.
The Ro-Ro (meaning roll on-roll off) boats arrived in 1923. For the first time, cars could roll on and roll off the boat. Oh my goodness, that brought even more summer people! And their cars!
Nothing warms my soul on a Ro-Ro trip to or from the island like a cup of ferry-chili. Hot and spicy and full of beans and onions and a little burger, it’s the perfect comfort food.
Maybe, someday, the powers-at-be will re-brand the perfect taste treat “Ro-Ro Chili”.
5. Giordano’s and Homeport: where restaurants on the island began.
Locations: Oak Bluffs (Giordano’s) & Menemsha (Homeport) | Best for: Pizza and pasta at Giordano’s; lobster and other seafood at Homeport; old-school island vibes at both
The 1800s brought summer people, a mania for self-improvement and a desire for a more perfect world. Interest in wellness, lifelong learning, lectures and salons lured artists and playwrights and poets and novelists to the island. The beauty, the peace, the quiet, the light, the mood are a creative cocktail.
Sadly that creative cocktail had no public landing spot until the 1930s. That when the first restaurants - real ones, with menus and a wait staff - emerged on the island. Before that, taverns and inns served set fare to travelers, but places that focused on food and conversation were missing.
Giordano’s and Homeport are the two oldest-standing restaurants on the island. Giordano’s is the OG of Oak Bluffs: red sauce, pizza, family-style everything. Homeport, in Menemsha, brings seafood, sunsets, and lobster rolls, a feel of ocean breezes and the taste of summer freedom.
Bonus Stop: The Sweet Life (Literally).
Want a place that blends food, art, and the Vineyard’s long-standing obsession with self-improvement? Sweet Life Café in Oak Bluffs hosts intimate author dinners where the conversation is as nourishing as the meal.
Final Thoughts
Martha’s Vineyard is, and always has been, about faith and farming, the arts and, most of all, community. To understand the history, you could bury yourself in books. Maybe memorize a key date or two. But I were you, I’d follow the food. Because history isn’t something you learn from a textbook. It’s a story you can actually experience, one bite at a time.
For other stories about experiencing history, bite by bite, check out
Traveling through a wormhole in Monemvasia, Greece, gave me a chance to see, hear, taste, smell, and touch a bit of the past.
Cook and eat with locals when you travel! Tasting the history of Crete with Ozlam and Traveling Spoon.
I love your comments! Feedback! Requests! Leave any and all here!
The Specifics:
Orange Peel Bakery
tel:+15086452025
682 State Rd, Aquinnah, MA 02535
julivanderhoop@gmail.com
Grace Church Lobster Nights
P O Box 1197
Vineyard Haven, MA 02568
(508) 693-0332
SteamShip Authority
Schedules available.
Giordanos
18 Lake Ave.
Oak Bluffs, MA 02557
508-693-0184Ho
Homeport
Menemsha, MA
508-645-2679
Agricultural Hall Farmer’s Markets
35 Panhandle Rd.
West Tisbury, MA
Wednesday and Saturdays, 9 - noon
 | A guest post by
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Thanks for inviting me to collaborate on this, Anne! I love finding ways to see MV from a new POV and now I see these foods with new appreciation!
Such an amazing round up! And I totally agree about Bow - he’s a wealth of knowledge!