Favorite Cruising Destinations by Boat - Oak Bluffs, MA

Posted by Mark Barret

Whatever you do, don’t call it Oak’s Bluff. The natives take offense at that.

As you approach Oak Bluffs Harbor from sea, you’ll be greeted by steep, sandy cliffs with large houses lined up across the top. The harbor entrance is narrow and difficult to see at first, but if you keep looking towards the ferry pier you’ll see boats going in and out, and when you get a little closer you’ll be able to pick out the red day marker on the end of the jetty.

Oak Bluffs, Marthas Vineyard, MAWhen I’m asked about my favorite New England harbors, for some reason, Oak Bluffs always comes to mind first. Many cruisers would beg to differ, claiming that it’s too crowded, too noisy at night, not great for swimming or fishing off the boat... Really, then, what’s so great about it?  

It’s extremely well-protected, for one thing. The entrance is narrow and points directly northeast, a direction from which it rarely blows during the summer boating season. The prevailing south westerlies are buffered by land and buildings, so even when its rough and windy out in Vineyard Sound, there’s hardly a ripple on the surface of the water inside the harbor.

Oak Bluffs Marina, which is town-owned, has 81 slips and 50 moorings packed into the small harbor. You can make slip reservations by calling the harbor master or just motor in and pick up a mooring on a first-come, first-served basis. They allow as many as four boats to raft up on a single mooring, so it is very unlikely that you won’t be able to find a spot.

If you are looking for peace and solitude, or you are an antisocial boater, Oak Bluffs Harbor is probably not the place to visit. There seems to be an unwritten rule that you cannot deny a request to raft-up, so if you pick up a mooring, chances are pretty good that you will end up with a boatload of strangers next to you. The slips along the perimeter of the harbor are not conducive to privacy, either. With your boat backed in against the bulkhead, curious pedestrians walking by on the sidewalk above have an unobstructed view right into your cockpit.

The moorings are tightly packed, and sometimes the clumps of rafted boats swing alarmingly close to each other. However, the tight confines of the small, calm harbor make it convenient and easy to get back and forth from shore in your dinghy, something you will greatly appreciate if you are one of those die-hards with a rowing dinghy. There is a liquor store and market in one corner of the harbor that has its own dock, affording visiting boaters one-stop shopping for provisions. If you don’t have a dinghy, you can get back and forth to shore in the town launch, which answers to channel 71 on the VHF.

As far as shower facilities go, which is an especially important consideration for cruisers, Oak Bluffs Harbor offers a couple of options. There is a building with public restrooms right on the edge of the harbor where the showers are sufficient, but not what you would call deluxe. Tokens cost two dollars and provide about five minutes of low-pressure, lukewarm water in a semi-private stall. I used those somewhat skeevy facilities for years before someone clued me in to the other option, which was to walk over to Summer Camp, formerly The Wesley Hotel, where, for a fee paid at the front desk, they hand you a fluffy towel and direct you to one of their individual private bathrooms. The bathrooms in the hotel are stocked with soap and shampoo, the water is hot, and the pressure is excellent. It is well worth the short walk and the higher price.

As far as choices for drinking and dining, Oak Bluffs is world class. Bars and restaurants line the waterfront, the kinds of places where you can sit outside - at street level or up above on a deck - and enjoy a summer cocktail while gazing out over the harbor. There are many great places to eat breakfast lunch or dinner within a short walk from the dinghy dock, and the main drag through town, Circuit Ave, is home to one-of-a-kind stores and boutiques. You are on Martha’s Vineyard, the land of the rich and famous, so keep your eyes peeled for celebrities and ex-presidents.

If you are cruising with kids, there is plenty to amuse them in this quaint and historic harbor town. There is an antique carousel, purportedly the oldest in the country, that spins remarkably fast while young riders stretch out and try to grab the proverbial brass ring. There are several places to rent bikes, and even Jeeps and Mini Coopers, or you can hop on a bus and go anywhere on the island for just a couple dollars. There is an old-school movie theater in town and a decent beach and a wide-open park to throw a ball or a frisbee. And last but not least, you can walk through the old Methodist Campground, which some people call “the quaintest place on earth.” There are more than 300 tiny gingerbread cottages in the campground arranged around a magnificent open-air tabernacle.

Back on board at your mooring, you might see people swimming off their boats in the harbor, but I’m not sure I’d recommend that. There are too many boats packed into a tight space with the possibility of holding tanks being illegally pumped overboard. But you don’t need to go into the water to keep entertained. It’s enough fun to just sit on your boat and take in the sights. There is always something going on.

I usually throw a line over when I’m just sitting there on a mooring and there is this one particular memory I have in Oak Bluffs Harbor. I was with my daughter, who was really little at the time, and still in that stage when she was fascinated with fishing. She thought she hooked a big one that day, and after a big struggle, she finally hauled it up. It turned out to be a perfectly intact canvas deck chair that must have fallen off a boat.

She’s grown now, and I haven’t been fishing with her in a long time, but every now and then she’ll bring it up.

“Dad, remember that time when we were in Oak Bluffs, and I caught a chair?”

I suppose it’s memories that make certain harbors our favorites, after all.

This is just one of the many beautiful harbors to cruise in New England. Our team have been boating on New England waters for many years and have fond memories. We will continue to share more of our favorite destinations in our Blog in the days ahead and we encourage our readers to do the same. If you have a story you would like to share, please contact us today. We also encourage you to share your memories and photos on our social media sites.

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Topics: best boating harbors in massachusetts, Best Harbors in New England, best boating areas in new england, Cruising New England Harbors, Best Harbor Favorites, local boating places, favorite boating destinations, boating destinations oak bluffs ma

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