Where to Eat:

• Nancy’s on the harbor is great for all occasions. They have food ranging from a burger and fries to scrumptious seafood dishes that melt in your mouth. On top of that there are many dining options all in one location. If you just want a quick bite to eat, order from the snack bar and eat outside under the warm summer sun. Perhaps you want to enjoy a nice refreshing drink and some appetizers with your friends; I suggest sitting on the upstairs outdoor patio over looking the harbor. Last, but certainly not least, if you need some air conditioning after a long day out in the sun dine inside. You still have an amazing view of the sunset over the harbor, and the dining fare ranges from burger and fries, and incredibly creative seafood dishes. Adults: if it’s after 5pm, you have to order a drink from Donovan. He has become a staple at Nancy’s and creates some of the best adult beverages on the island. I suggest the Donovan’s Delight or the Dirty Banana, they are his signature drinks and are absolutely delicious.
• Coop De Ville is also located on the harbor, but it’s more low key. “The Coop”, as the locals call it, has a very relaxed atmosphere offering casual family dinning including lobsters, steamers, fried clams, and chicken wings. They even offer a Raw Bar.
• Just off the harbor is the Martha’s Vineyard Chowder Company, which provides a relaxed family atmosphere with a sophisticated flair. ‘Cho. Co.’ makes their award winning chowder from scratch every day; also they have a fresh raw bar where you can order oyster ‘shooters’. For example, the Citrus Vodka Shooter is an oyster topped with cocktail sauce, Tabasco sauce and a dash of citrus vodka. Other offerings include nightly specials, fresh seafood, and many other succulent options.
• In the mood for a fun atmosphere with a unique twist? Visit Sharky’s Cantina, for an authentic Mexican meal and fresh Margaritas. Sharky’s is known for its laid back family atmosphere, great service, friendly staff, and their large portions. If you order the nacho’s thinking it will just be enough for one, think again! They have 12 ooey gooey layers stacked high enough to feed 2-3 people, and that’s the regular size! I suggest ordering either the fajitas with the marinated stake, or the Grandios Burrito. Don’t worry about bringing young children to this restaurant; they provide crayons and coloring books, as well as a kids menu.
• Last but certainly not least on our list is the Offshore Ale Co. Here they brew their own beer, and serve hearty traditional meals such as fish and chips, meat loaf, and bangers and mash. One of my favorite things they have there is the specialty pizzas they serve from their wood fired brick oven. My favorite is the Chicken Pesto pizza. I order it all the time!

What to do:

• Visit the Flying Horses Carousel. I have so many amazing memories from coming here with my parents, and even working here as my first job ever. The Flying Horses is the oldest carousel in the country! Built originally in 1876, this carousel has been entertaining families for generations, and generations to come. Not only is it a carousel, but it’s also a game. Catch the brass ring and you win a free ride! under the same roof is a small arcade and concession stand. If you’re here with your family do not bother going on a rainy day, the line will be out the door. Instead, try coming later in the evening when the lines aren’t that long.
• Up for some water sports? Rent jet-skis from MV Ocean Sports located right on the harbor. You can also go para-sailing, tubing, and a few other fun activities with your family or friends
• If you’re traveling with younger kids, I highly suggest going to the arcade located right on Circuit Ave, the main street of Oak Bluffs. Kids will have a blast playing all the games and winning prizes.
• Oak Bluffs is home to many charter sports fishing boats, such as the Smokin Eel  or The Skipper. Many of the charter captains around here have been fishing the local waters since they were a little boy with their fathers. if you’re up for some great fishing I highly recommend one of these two boats. The Smokin Eel is a private charter boat that can take up to six people at a time for either a full or half day for inshore or offshore fishing. The skipper takes multiple families out for half day trips and only stays inshore. Don’t let that discourage you though, you can still catch a Sea Bass or Stripper during your trip.

Events:

• Hot Rod Weekend Between June 14 – 16 Oak Bluffs is home to the Boston Area Roadster Club. Every year this large group of antique and hot rod cars gather here to raise money for their charity of choice. Owner park their cars all along the harbor, letting you take pictures look either under the hood or at the interior of these beautiful vehicles.
• Harbor Fest Every year the residents and businesses of Oak Bluffs put together a festival on the harbor celebrating the arrival of summer. This year, on June 22, there will be live bands, great food, and local artisans selling their wares under pop up tents.
• Summer Solstice Fireworks All day long their will be events throughout the town, culminating in fireworks at 9 PM
• Monster Shark Tournament July 18 – 21. Every year serious big game fisherman gather on our little island for two days of shark fishing. The biggest shark wins. On Friday and Saturday between 3 – 7 pm you can gather at Our Market on the corner of the harbor and watch all the giant sharks being weighed in.
• Grand Illumination Every year in the middle of August, before school begins and people start to head back to their normal lives, the gingerbread cottages behind Circuit Ave hang lanterns from their porches and decorate. At exactly the same time everyone lights their lanterns and the neighborhood is transformed into a magical little village for a couple of hours.
• End of Summer Fireworks  Fireworks held every year to end the summer season with a bang. This year the fireworks will be August 16 at around 9 PM. The best viewing spot is from Ocean Park. Get there early because seating will be scarce.

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