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Lively harbors: Oak Bluffs, Martha's Vineyard MA

Jan 25, 2007
Cal Cal 33-2 cape cod
There are quiet anchorages, harbors, and moorings. I'm writing about the opposite, lots to see close by: Jet ski's on dinghy dock, waterfront live music & numerous bars/restaurants, loud parties, scenic ginger bread homes, flying horses carousel, green panoramic ocean view lawn with gazebo, Nancy's famous Mudslide (dirty banana), boats rafted together like Lake Havasu spring break, drunk folks falling into launch, tourists clogging sidewalks, shops of all kinds, and my pick is Oak Bluffs. . A+ for Oak bluffs marina, nice help tying up, ect... How about your favorite over-populated spots? ***note: Only sailboat on the back pier...Amen to Bose noise cancelling headphones!


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Likes: BarryL
Jul 19, 2013
Pearson 31-2 Boston
Haha. I spent a night tied up in Oak Bluffs about 48 years ago and I have to say I haven't been back. I guess if one is single, having a good selection of bars nearby and the ability to stumble back to the boat without a dingy ride, commends the spot. If you haven't yet done so, try an evening on anchor in the Vineyard Lagoon, and then you might start a thread on "Quiet, beautiful spots no one knows about...".


May 21, 2004
Jeanneau Sun Odyssey 409 Mt. Sinai, NY

My vote would be Mitchell Park and Marina in Greenport, NY. Lots of bars and restaurants near by. Lots of powerboats. Music going all night from the waterfront bars. It's a hoot!

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Likes: shemandr


Alden Forum Moderator
Jun 22, 2004
Alden 38' Challenger yawl Rockport Harbor
Ha! Funny post. On Martha' Vineyard, our favorite busy harbor is Edgartown. We like the anchorage outside (in the right weather) for it's privacy but enjoy all that is going on around.

For a crowded harbor down your way, Cuttyhunk is tops. It can be noisy on the moorings but the anchorage feels a world away.
Cuttyhunk shoal anchorage 2 (1 of 1).jpg

9 out of 10 times there, we've found space inside the pond to anchor.

Cuttyhunk sunset_.jpg
Jul 19, 2013
Pearson 31-2 Boston
Ok, then I would offer the Nantucket Boat Basin as the holy grail for this search. A dozen plus bars and good restaurants, and a chance to rub elbows with the rich and famous.
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Likes: TomY
Jul 5, 2011
Oday 28 Madison, CT
We have a friend that got caught in a nasty storm there maybe 3+ decades ago. He had trouble securing his boat and a man ran up and helped him. After that, both of them were soaked and it was getting dark, so the man invited my friend over to his house to shower, dry out and get some food. Imagine my friend's shock when he walked in to the guy's living room and there were Art Buchwald, Lady Bird Johnson and Walter Cronkite, all who welcomed him warmly as a sailor braving the elements. Pretty amazing, but one can't make this stuff up.....
Jan 1, 2006
Slickcraft 26 Greenport, NY
Greenport bar owners think too many boaters drink on their boats...
I'd have to nominate Paynes (Best Mud Slides), Champlins or Block Island Boat Basin. But also Put-In-Bay where beer is sold in buckets.
You can find bucolic-icity at Coecles Harbor during the week, Essex, Jamestown, West Harbor on Fisher's Island, Kelley's Island among other places too secret to mention.
Jan 1, 2006
Slickcraft 26 Greenport, NY
Block Island doesn't really get going until the 4th. June is pretty quiet. When the Off Soundings fleet and the Block Island Race Week fleets are there in June it is the de facto beginning of their season. The weather can still be cool and it can be foggy. Usually we have the place to ourselves. It is a good time to be there! Summer peak got to be too much commotion for us. The competition for moorings, the crowded restaurants, the crowded side walks, made it less fun. The worst is when the NYYC stops there on their summer cruise. Just awful. On the other hand Winter visits by ferry were more fun. Especially if you hit a Blue Moon and see the naked ladies dancing around Rebecca.
There's a book "Spy Island" about BI which is worth a Kindle read. It's a fun read if you've been there. Or Coney Island.
May 28, 2015
Catalina 385 Long Branch, NJ
Block Island Boat Basin … walk from your boat to a mudslide at The Oar … and my favorite home port … Atlantic Highlands Harbor in NJ … a launch ride and walk to “On The Deck” and dozens of other spots within a walk or bike ride.
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Oct 26, 2008
Catalina 320 Barnegat, NJ
Montauk Harbor would be a great place for a spectacle. It doesn't have the upper crust feeling, except maybe around Star Island. It is probably changing but I always thought it had the working man's dock atmosphere, with a prominent commercial fishing fleet around Gosman's Dock. We've enjoyed several dinners at Gosman's when we used to bring our ski boat out to launch at the municipal ramp on Lake Montauk. I didn't see many sailboats in that area, except on the other side of Star Island in the Lake Montauk anchorage. I'm not sure how friendly it is for dinghy access. It didn't seem like there was anything available except maybe by the boat ramp.
Jun 14, 2010
TBD Looking for my next boat CT
I'm not sure how friendly it is for dinghy access. It didn't seem like there was anything available except maybe by the boat ramp.
I haven't been there in at least 10 years, just for that reason. Once was enough. It seemed to me the only way to feel welcome there is to reserve a slip. That's not my preference (and as a multihull we're usually assigned to outside face docks at higher rates). I prefer paying a more reasonable price for a transient mooring, or anchoring out.
Also, it's a Mecca for the sport-fishing crowd.
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Bob S

Sep 27, 2007
Beneteau 393 New Bedford, MA
Been sailing these areas for years. Pretty lucky to have so many destinations within a days sail. We've been in OB many times and it is a zoo. They allow up to 4 boats rafted together and it can be a nightmare weaving through them as they swing on the moorings. The Admiral loves to dance and we've found OB and Edgartown to have live music and dancing. We're the geriatric pair;)! OB had a beer festival that was a lot of fun but didn't happen last year due to Covid. Not sure if they plan one this summer
OB Beer Fest.JPG

OB Beer Fest 2.JPG

Anchored inside and out of Cuttyhunk but it's the polar opposite of OB. Our favorite has to be Block Island. We get around with folding bikes, dance at Ballards, cocktails and appetizers on the deck of the Spring House and Mudslides at Oars. What's not to like!
Jan 1, 2006
Slickcraft 26 Greenport, NY
With regard to Montauk I believe you can still anchor in the Lake but there are private residential properties all around it so no dingy landing on those. I think in Suffolk County any road dead end at the water is public property. There are several dead ends on the lake. No hint of security. I would say it's a stay on the boat rest stop to or from other New England destinations. I think the inlet was dredged in the past few years but it wasn't deep enough for larger sailboats at low tide.
The Montauk fishing village is mostly commercial but you do see sailboats up on the hard there. When you see the prices in the formerly fishing bars you won't think you are in a working class town any longer.