top of page
  • Writer's pictureRichard Phillips

Oh, Martha! Where's Your Vineyard?

Let's talk about my favorite place to visit on Planet Earth. Other than the lovely small town in Alabama where I hang my hat, a place around 1,200 miles from my front door has my heart. The northeast is a beautiful place. Autumn, spring, whenever, you'll never be disappointed with the views, the food and the atmosphere. I try to make a pilgrimage each year to my spot in Massachusetts, a small island called Martha's Vineyard (MV). Located approximately 7 miles off the coast of MA, Martha's Vineyard has a long, rich history. I'll let you discover who Martha is on your own and focus on why I feel so drawn to this picturesque island.

Where: Martha's Vineyard, Massachusetts

How I got there: Fly or drive (it's a beautiful drive, especially in autumn)

How much: Off season rentals are affordable

Need a car: I'd recommend it

Most people think of Martha's Vineyard as a fancy-schmancy place where celebrities and presidents go to vacation, and that is true, but that's not the whole story. MV opens for its busy season on Memorial Day weekend and closes out after Labor Day. So yes, if you go during the peak season you'll pay a ton of money to rent a place, eat and shop. However, prices drop DRAMATICALLY after Labor Day...sometimes by 60% or more. I choose to go in the off season. It saves money and, honestly, I prefer MV in autumn. It's a Hallmark movie, for real.

Within MV, several quaint and lovely towns dot the island. Most towns are very small with the few larger towns hosting the port authorities (where the ferry docks). The only way on or off the island is by ferry, so make sure you book your time slot well in advance because if there isn't room on the ferry, there is no "Plan B." You're just stuck! Of all the beautiful towns, my favorite is Edgartown. By far the loveliest setting, Edgartown sits on the eastern part of the island with a view of Chappaquiddick Island due west. "What makes it so special?" everyone asks, and that is such a frustrating question for me to answer. I can't make a "List of Why I love Edgartown" like you make a Christmas list. It's the atmosphere...the vibe. It's the smell of the air off the Cape; the perfectly timed breeze as you walk by well maintained picket fences; the fishermen unloading pounds of lobster on the docks; the historic homes, most with beautifully aged cedar shingles and front gates that gently squeak open. I feel so much peace on the island. It's an experience you have to have, not a story you have to hear.

My favorite place to stay in Edgartown is the Harbor View Hotel. There isn't a better place to stay, in my opinion, in all of MV. I have booked an Airbnb before, and that experience was wonderful, just not the same as this charming hotel experience. Perched on the island facing the Edgartown Harbor Light, the 117 room resort is within walking distance of literally everything and has a sunset view that will warm the coldest of hearts.

Walk downtown, rent a boat, have a picnic on the beach or just sip a cocktail on the wrap around porch. You really won't care what you do, you'll just be tickled to be there.

So once you're there, what do you do? Well, one thing you're gonna do is walk around. Edgartown is very walkable, with most neighborhoods, retail shopping and waterfronts closely situated. You can access almost any destination by foot. Now of course you're going to want to see the whole island and visit other gorgeous spots like Vineyard Haven, Oak Bluffs, Tisbury and West Tisbury. I normally rent a car to have, and I have even driven my own car the 1,200 miles!

Specifically in Edgartown, dine at The Wharf for yummy seafood in a casual setting right in downtown. For something a little more unique and upscale, try 19 Raw for amazing oysters, local seafood and caviar, if that's your thing. There are absolutely other amazing restaurants to visit...those are just two of my favorites. For a very cool vibe, and some beer and pizza, try Bad Martha Beer. Located just off the main drag, Bad Martha is a local brewery that serves brews and food. The only "bad" part of Bad Martha is in the name. Grab an IPA and some pizza and sit outside.

Other than food and drink, MV has many hot spots any visitor simply has to visit. Here's a list of my favorites, but I am sure you'll find your own.

Nantucket (an island all it's own)

I can't give out recommendations without a shout to my favorite place to stop for all things MV. From souvenirs, to coastal inspired items, to MV branded tees and candles, be sure to visit Refabulous Decor - 65 Main St, Vineyard Haven, MA 02568.

If you are visiting in the fall, pack for cool mornings, mild days and chilly nights. As they say, layers, layers, layers! And it is not uncommon for there to be a shower or two, so always be prepared with an umbrella and rain boots.

Each town on MV is different and special. Each has its own charm. Want to see the world's oldest working carousel? See it in Oak Bluffs. Need a smaller bay town vibe? Edgartown is your spot. Looking for more hustle and bustle, and a ferry off the island? Vineyard Haven will do it for you. And let's not forget one of the most popular clothing brands, Vineyard Vines, started on the island. Visit the original storefront in Edgartown and get a special clothing line only available there.

I hope you give MV a shot. It's a uniquely magical place that I know you would never forget. Even if it doesn't become your favorite place on Planet Earth, you'll make a memory or two.

Oh, and there's not a single vineyard on the entire island.

128 views0 comments

Recent Posts

See All


bottom of page