Presenting my latest guide for where to eat and drink in the down island towns of Oak Bluffs and Edgartown!! We have been backpacking around the island via the Vineyard Transit Authority bus system which is such a fun way to explore. Fast forward post Menemsha and Aquinnah days to Oak Bluffs where we stayed at our favorite harbor-front hotel The Dockside. (You can read my review here.)
I will go ahead and say the chicken wings at Coup de Ville (12 Circuit Ave Extension) are not to be missed when in Oak Bluffs. We started our evening at the casual open air waterfront shack with a couple beers - they have an extensive selection on draft - and ended up devouring a basket of their "World Famous Wings" ($12) on a whim. There are a ton of sauces to choose from such as: dragon fire, suicide, Jamaican Jerk, Cajun, New Orleans Voodoo and Maryland. 
We wandered the lively streets and happened upon a new whiskey bar 20byNine (16 Kennebec Ave) where we mingled with locals over cocktails and small plates. We loved the Smoked Bluefish Mason Jar ($10) with bacon jam and blistered tomatoes and enjoyed a unique take on Tuna Tartare as it meshed with bites of watermelon. Both dishes come served on handsome slate boards. The Johnny Cakes ($10) with strawberry rhubarb prove rather bland and insubstantial. 
I will go ahead and say the chicken wings at Coup de Ville (12 Circuit Ave Extension) are not to be missed when in Oak Bluffs. We started our evening at the casual open air waterfront shack with a couple beers - they have an extensive selection on draft - and ended up devouring a basket of their "World Famous Wings" ($12) on a whim. There are a ton of sauces to choose from such as: dragon fire, suicide, Jamaican Jerk, Cajun, New Orleans Voodoo and Maryland. 
The bartender shakes up exquisite cocktails; from a perfect Old Fashioned to creations like the Down Island ($12) with rye, lillet rouge, lillet blanc, maraschino liqueur + rhubarb bitters and the Paper Plane ($12) - bourbon, citrus, amaro nonino, aperol + hopped grapefruit.
The next day: South Beach (Katama) with a six pack of Rolling Rock.
The next night: Dinner in Edgartown at Rockfish (11 N Water Street). We really like both The Port Hunter and Alchemy but wanted to try somewhere new-to-us. Our hotel's virtual concierge named Loomis (you text him, he's a real person who lives on island!) recommended Rockfish and he did not steer us wrong. We started with terrific barrel aged whiskey cocktails - a Boulevardier for her and a Manhattan for him. The Wood Oven Charred Brussels Sprouts appetizer was on another level. I know, when are charred brussels sprouts not lust worthy? But - this dish has applewood smoked bacon, mashed potatoes and a ROQUEFORT FONDU. As far as entrees go, the Linguine alle Vongole and the Roasted Half Chicken were delicious.
Our final day on island was gloomy and rainy. We went for a run around Oak Bluffs Harbor and by all the whimsical, colorful gingerbread houses and throughout their respective little neighborhoods before the downpour.
After checking out of The Dockside we put our name in for a coveted table at Biscuits (26 Lake Avenue). This is the only place in Oak Bluffs that does a sit down breakfast on weekdays and their food is worth the wait. We had the Biscuits Benedict ($9.25), the South Beach Scramble ($7.25) and a side of Biscuits and Gravy ($3.25). Next we decided to visit to Bad Martha Brewery which turned into an all out Edgartown / Oak Bluffs bar crawl.
If you encounter a rainy day while down island and happen to be in a similar drinking mood, here's a look at all the fun: >> bus from Oak Bluffs to the stop just before Edgartown Post Office >>
Bad Martha Farmers Brewery (270 Upper Main Street) for beer flights followed by mason jars of your favorite brew; their flagship Martha's Vineyard Ale happens to be mine.
Sharky's Cantina (266 Upper Main Street) - just next door from the brewery for a thirst quenching Sharkarita! Add a fruit puree to any marg - from watermelon, mango and strawberry, to ginger and pineapple-mint.
The Wharf (3 Main Street) - meander by picturesque and historic houses on a 10-15 minute stroll into the main section of town to this cozy pub. We made lots of likeminded drinking friends here!
Atlantic Fish & Chop House (2 Main Street) - just across the cobblestone street for their signature bar side bacon and a big glass of rosé. The sun is starting to peek out and a stroll around the wharf is in order.
>> bus from Edgartown Post Office back to Oak Bluffs >>
Sand Bar & Grille (6 Circuit Avenue Extension) - It is full on gorgeous sunshine at this point so Painkillers on the dock front sand bar it is!
The Lookout (8 Seaview Ave) - Sushi time! We scored two seats at the tiny sushi bar nestled among this rowdy tavern. Special thanks to our waitress for not judging us at this point in our crawl ;) But we're still going strong with cute little jars of cold Gekkeikan Sake. Soon its time to grab our bags and catch the last Friday evening ferry home to the mainland.
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Thank you for making it through this long food and drink crawl filled post! I hope these recaps can serve as a solid guide if you visit Martha's Vineyard. And if you've been, let me know if you have a favorite spot that I missed! 
