📆 Guest Itinerary: Trusted Tables’ Self-Guided Food History Tour on Martha’s Vineyard

A 2-day food tour through Martha’s Vineyard history (with 5+ food stops!)

Jul 02, 2025

Readers: I’m excited to share today’s guest itinerary from

! Many travelers come to Martha’s Vineyard looking for the best FOOD. Anne writes about food on MV while weaving in culture and experience, head to Trusted Tables to read more!

You can read Anne’s Version here:

Trusted Tables

A 5-stop Martha's Vineyard food tour that tells the history of The Vineyard, bite by bite.

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…

9 days ago · 4 likes · 3 comments · Anne Manning and Elisabeth Bluford

🍴 Want more than 5 Stops? Here is a 2-Day Martha's Vineyard Food Tour:

🗺️ Two-Day Martha’s Vineyard Food History Tour

📍Day 1: Down-Island (Oak Bluffs ➝ Vineyard Haven)

Ideal for a Friday

8:00 AM – Start with breakfast at Biscuits, a beloved Black-owned diner near Inkwell Beach
9:00 AM – Stroll the MVCMA Campground and admire the iconic gingerbread cottages
10:00 AM –Visit nearby African American Heritage Trail sites to reflect on the island’s civil rights legacy
11:00 AM – Early lunch at Giordano’s for red sauce classics and a slice of island restaurant history
Travel to Vineyard Haven
1:00 PM – Explore the Martha’s Vineyard Museum for a thoughtful look at island life through the centuries
3:30 PM – Wander Main Street Vineyard Haven and pop into local shops

Pro Tip: Foodies should browse LeRoux — it’s packed with locally made goods that travel well

5:00 PM – Lobster roll dinner at Grace Episcopal Church (Fridays only; order ahead or walk up)

📍Day 2: Up-Island (West Tisbury ➝ Aquinnah ➝ Menemsha)

Ideal for a Saturday

9:00 AM – Visit the West Tisbury Farmers’ Market at the Ag Hall – Weds & Sat

Lis's Picks: Pie Chicks, Morning Glory Farm, Kulture Club Kombucha

10:15 AM – Stop at Grey Barn and Farm for farmstead cheeses and a peek at new-era sustainable farming
10:45 AM – Visit Allen Farm to see the sheep, shop for wool, and take in sweeping Up-Island views
1:00 PM – Stop by Orange Peel Bakery in Aquinnah for fresh bread or sweet pie; experience the Wampanoag spirit of community and tradition
3:00 PM – Head to the Aquinnah Cultural Center for a deeper understanding of Wampanoag history and heritage
5:00 PM – Early dinner at Homeport Restaurant in Menemsha for lobster, seafood, and dockside views