A Day in the Vineyard (Wine Optional)

Martha's Vineyard Lighthouse
The Lighthouse at Aquinnah

Martha’s Vineyard – long the playground of New England’s elite – lies just a ferry ride off of Massachusetts’ southern coast. This iconic summer destination also welcomes flights from around the country, including those of private pilots. Thanks to the latter, (namely, my Dad) I was able to see this Norman Rockwell-esque outpost for myself. And what I found, was that it was well worth the hype.

Let me start by saying that despite its name, I didn’t have a drop of wine during my one day jitney, though not for a lack of upscale restaurants. Instead I focused my attention on the charming towns and appealing beaches that are never further than a short bus ride away. In fact, it was the efficient and comfortable bus service that in my mind gave Martha’s Vineyard the edge over similar Atlantic islands such as Block Island.

The airport is located near the dead enter of the island, and from there the island’s main destinations: Edgartown, Oak Bluffs, and Aquinnah, form a triangle that is somewhat equidistant in each direction. The useful Martha’s Vineyard Transit Authority runs regular bus service to all corners and is by far a more economical option than renting a vehicle on your own. That said, you’re at the mercy of their timetables, so choose which means most to you.


Edgartown, Martha's Vineyard
Charm out the wazoo in Edgartown, Martha’s Vineyard

Heading east from the airport, the first destination is Edgartown – a quaint New England town sporting a wide array of restaurants, art galleries, boutiques and of course, souvenir shops. This is the gateway to the (in)famous island of Chappaquiddick and you’ll find the water brimming with watercraft come summertime. Allot at least an hour to leisurely stroll the shops and streets – more if you want that aforementioned bottle of wine. This is also a good place to catch a bus to South Beach for a fine stretch of sand with very basic public facilities onsite.

Oak Bluffs

If you’re arriving to Martha’s Vineyard by ferry, it’s quite likely that Oak Bluffs is where you’ll disembark. This charming town at the northern tip of the island is known for it’s ‘gingerbread houses’, and is a flurry of activity in summertime. If you’re into eclectic shops and colorful architecture, spending time in Oak Bluffs will leave you happy.


On the Western point of the island is the tiny hamlet of Aquinnah – which is sometimes also called by its clearly-not-named-in-this-century moniker Gay Head. This section is a quiet piece of serenity marked by tall clay cliffs looking out into the sunset. There’s a decent stretch of boulder-strewn beach nearby along with a lighthouse and scenic overlooks. There’s even a small cluster of shops and restaurants (with sunset views!) near the bus stop. For a little peace and tranquility, this is a great place to come in the early evening to relax and smell the sea grass.


Martha’s Vineyard is a summer destination that not only is worth the hype, but handles its popularity with stoic dignity. I would heartily recommend it to anyone looking for classic New England charm, ocean views in nearly all directions, and a nostalgic sense of summers of times past. It’s as a good a place as any to while away the lazy days of summer – with or without a bottle of wine.

Stop and smell the flowers in Aquinnah

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