MV for Newbies: Lay of the Land
Martha's Vineyard is rather large, with about nine towns/areas, all with very different vibes. There are pros and cons to staying in every area, which I've laid out below.
⦿ "Down Island" (Edgartown/Katama/Oak Bluffs/Vineyard Haven)
⦿ "Up Island" (Chilmark/Aquinnah/Menemsha)
Edgartown
✦ Personal Favorite
If you’ve been to Nantucket, Edgartown is similar to Nantucket town (and my dog Edgar's namesake!). It’s a gorgeous whaling village with a traditional/preppy vibe, with lots of great restaurants, shopping, an most of the island’s hotels.
The benefit of staying in town is obviously you walk out the door and there's tons to do, but the downside is it’s therefore the priciest area. It has access to beaches, but not the best on the island.
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Katama
Katama is technically part of Edgartown, but there's no real town there, just a cute general store. It's a gorgeous, flat area with easy access to South Beach, one of the biggest public beaches with open parking.
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Oak Bluffs
This is the historically Black area, with the famous Tabernacle, Gingerbread Houses, and Inkwell Beach. Circuit Avenue is the main drag and has a Jersey Shore boardwalk feel. The larger OB area has a lot of great, well priced houses, and if you want to be very OG MV, you can rent one of the famous gingerbread cottages, which are rustic but adorable.
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Tisbury/West Tisbury
This a large part of the island that's more remote with nothing beyond a general store in terms of a town, but it's great for how quiet it is, its centrality (about 15 minute drive to Edgartown, Vineyard Haven or Oak Bluffs), and its access to Lambert's Cove Beach, one of the best on the island.
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Vineyard Haven
✦ Party Location
Another charming town with some great shops and restaurants down Main Street, and beautiful harbor views.
For reference/planning, the party will be here Saturday night.
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Chilmark
Other than Edgartown, this is my favorite part of the island. It's more wild and remote, almost like you're in the English countryside. The island becomes more hilly here, and therefore the beaches are spectacular with the famous red clay cliffs. There's one restaurant (the excellent Chilmark Tavern) and one store (Chilmark Store), where you often see celebrities like Larry David (this is where he famously yelled at Alan Dershowitz! A lot of celebs live up there bc of how private it is).
If you stay in Chilmark, you get access to Lucy Vincent and Squibnocket beaches. “LV” is the best on the island, my all time favorite (and what Mom named her dog after!), which is a major plus to staying there.
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Menemsha
Tiny fishing village where Jaws was filmed. Known for Larsen's Fish Store and sunsets on the beach.
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Aquinnah
The farthest point of the island, with a tiny town that leads to the famous lighthouse and cliffs, which are a must see.
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Chappaquiddick
Island across the harbor from Edgartown where you take the “On Time III,” a 3 car ferry to get there. Because of the need for the ferry, I’d only recommend staying on Chappy if you have friends who live there, or want to experience something rather remote.
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