Brian hops the Steamship Authority ferry from Woods Hole and steps straight into Oak Bluffs — the town the episode affectionately calls "Beach Vegas." It's a day-trip blueprint: what to eat, what to skip, and why you should get back to the dock early.
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Where the episode goes
Off the ferry and into Circuit Avenue, Oak Bluffs' buzzing main drag. First order of business: what the episode calls the best clam chowder in New England, at Martha's Vineyard Chowder Company, chased with frozen drinks that scream vacation mode.
Then comes the episode's comedy centerpiece — a full hat makeover at a legendary local shop, with Brian cycling through transformations until the right one sticks. Add quirky shopping, beach time in lobster-print shorts, and rental daydreams (Jeep? Vespa? convertible?), and the day fills itself.
The ending is the tip you'll remember: they miss the ferry — and get rewarded with a gorgeous unplanned sunset in Vineyard Haven. Arrive at the dock early; but if you don't, the island has a consolation prize.
Episode moments
- 00:53 — Arrival in Oak Bluffs and Circuit Avenue energy
- 04:03 — Frozen drinks and island eats
- 06:41 — The hat shop adventure
- 19:34 — Beach time and the sunset wrap-up
Episode FAQ
How do you get to Oak Bluffs for a day trip?
In the episode, Brian rides the Steamship Authority ferry from Woods Hole on Cape Cod directly into Oak Bluffs. His hard-earned tip: get back to the dock early for the return trip — he missed his ferry.
Where does Brian eat in Oak Bluffs?
The featured food stop is Martha's Vineyard Chowder Company on Circuit Avenue, which the episode crowns the best clam chowder in New England, along with frozen drinks and island snacks.
Who makes The Wandering Bostonian?
The episode was directed and shot by Paul Speziale, edited by Cahl Benecchi, and produced by Brian Pitcher, Ernesto Galan, Paul Speziale, and Ryan Williamson, with production by Nidhogg Studios.
Behind the camera
This episode is a Nidhogg Studios production.
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