On island beer garden. Great atmosphere, better beer! Dog and kid friendly. Cheese boards galore!
Delicious food and drinks that can be enjoyed on the lawn with live music. Kid friendly, open day and night!
Small plate and Tapa style bites. Open for lunch and dinner. A total treat!
$1 oysters from 5pm-6pm everyday! This is probably our favorite date night spot... and favorite spot to meet and make friends at the bar. A little upscale.
An island staple. Good for a sit down meal or take out style eating along the Oak Bluffs Harbor. Don't forget to wait in line for a Dirty Banana!
Owned and operated by friends, this is our favorite little breakfast spot on island. Mikey says get the double stacked waffles.
Breakfast takeout to hit on your way up island. If you get the breakfast sandwich, ask for the special biscuit.
Menemsha is an authentic fishing village located in the rural town of Chilmark. It's an iconic spot to set up a little beach picnic and watch the sunset. There are little shops, take out food, galleries and more in the town. We recommend heading up about an hour before sunset and making a night of it!
There are so many hiking trails all over the island, Menemsha Hills tends to be the favorite. It's an easy to moderate hike, leading to endless water views.
The Aquinnah Cliffs are located on the far west side of the island, land that still belongs to the Wampanoag natives. They are a national landmark that really shouldn't be missed. The ride alone is worth the journey allllll the way up island. (take Middle Road!)
The country's oldest carousel- an iconic Vineyard attraction.
One of Paulina's favorite things about the island is the local art. The Granary is the island's oldest gallery and carries quite an impressive collection. (You should check out the Field Gallery too)
An eclectic general store filled with local produce, candy, toys, and gooood coffee. Definitely stop in on your way up island.