After cancelling a couple of trips early this month due to nearby hurricanes, Mrs. Horne and I decided to take a spur of the moment overnight cruise on Tuesday.

She was arriving that morning after caring for her dear mother Doris and I had no idea exactly where we were going until she arrived.

I was determined to go somewhere we hadn’t visited this summer and about 15 minutes before we left the house, I settled on Oak Bluffs.

I love offseason cruising because the slips cost less, it’s less crowded, and you can pretty much dine anywhere without a reservation.

I favor autumn over spring because the weather tends to be milder – unless there’s a hurricane passing offshore.

The Horne History at Oak Bluffs 

It’s funny that we hadn’t visited Oak Bluffs in at least 6 years. For decades it was our family’s primary destination.

Back in the 1970’s and 80’s, it was my parents favorite destination in Aquarius – our Pearson 35 sailboat. It’s less than 20 miles from Mattapoisett and with the prevailing Buzzards Bay Southwest winds, typically a day Sail.

In 2001 after buying my first boat (26’ Boston Whaler), it was our destination on the roughest trip I’ve ever experienced coming home from Martha’s Vineyard. 

Despite the trauma of that day, Oak Bluffs was probably the top destination for the Whaler thanks to its virtually guaranteed Dock and Dine opportunities. More often than not, we’d take the town bus to Edgartown and have lunch at The Seafood Shanty.

In fact, if you own a 20-30’ boat, Oak Bluffs is the perfect place to go for a day trip moor and island visit.

Oak Bluffs offers 105 slips for overnight cruisers during the summer season. The slips aren’t ideal in that they’re a fixed dock, pilings, and most don’t have finger piers.

Oak Bluffs is Dock and Dine paydirt for midsized boats in that they offer dozens of moorings and permit rafting of up to 4 boats. This means you’re virtually guaranteed a tie up – even on a Saturday in July.

Autumn Gold

Oak Bluffs is probably the most classic summer destination on Martha’s Vineyard. It offers a lot of moderately priced restaurants on the water with all those fattening dishes we crave from our youth. It also has the longest operating carousol in America. 

Despite its carnival atmosphere during the summer, it seems to close down faster than Vineyard Haven or Edgartown in the fall.

A number of summer hot spots were already closed for the season when we arrived on September 26th and most of the shops had End of The Season sales.

I booked Vigilant’s stay on Dockwa and immediate called the Marina ‭(508) 693-4355‬) to request a premium slip.

“Do you want a finger pier” said the Harbormaster. “Yes please” I quickly replied.

Daisy’s Big Boat Trip

Our plan for a quick one night getaway, so we brought our fiesty little West Highland Terrior – – – Daisy.

Daisy hates riding in the car and she’s terrified of water – what could go wrong?

She also worships Mrs. Horne, so as long as she was tucked up next to her, she was happy.

The fog lingered across Buzzards Bay which made Mrs. Horne very nervous. Woods Hole had low visibility, but nothing like two weeks ago when I went through it with Peter and Rudy.

As nerve wracking as it is staring at instruments instead of enjoying the view, it is absolutely exhilarating when a landmark pops out of the fog.

East Chop Lighthouse (I think)


By the time we tied up at Oaks Bluff, it had turned into a beautiful autumn day.

We took Daisy to the only dog friendly restaurant in town – The Offshore Ale House. All they sell is their own beer so Mrs. Horne got brave and tried a golden ale.

We split an incredible fish sandwich, but we were so hungry that I forgot to take a picture before we devoured it.

The sandwich came with a mountain of truffle Parmesan fries – probably the best I’ve had of late. I did snap a picture of what was left after we had our fill.

My brother in law Paul always orders his fries “well done” and he would love these crispy beauties.

Good Enough for Obama

After a relaxing afternoon on Vigilant reading, we ventured out to Red Cat Kitchen for dinner.

As I mentioned, some restaurants had closed for the season and others simply shut down on slow nights and it was a Tuesday!

We really lucked out with Red Cat Kitchen. It turns out that this is one of Obama’s favorites and our server Erin waited on the ex-president and his family every time he ate there.

Erin – Server of Presidents!

I’ll do a full Seaside Eatery review later, but suffice it to say the food was great.
Mrs. Horne started with a Caesar style salad while I munched on the very fresh warm bread and spicy oil.

Although a number of things on the menu caught our eye, we decided to be adventurous and went with the chef’s tastings.

These are surprise dishes ($14 each). Erin recommends 3 per person ($42) unless you have salad first, then she suggests two which is what we had.

The first was a crispy shrimp salad…

The second was a veal and island grown mushroom dish.

After dinner the chef Ben came out to introduce himself and ask us how we enjoyed his tastings.

Chef Ben

By the way, the atmosphere was very chic and quite crowded (for a Tuesday night in late September).

As we were leaving, the couple next to us asked what the tastings were and after we finished telling them ever little detail Erin appeared, overheard us, and said to the young couple “yours might be totally different”.

All in all it was a great day and we returned to Vigilant planning on checking out breakfast before returning to Mattapoisett.