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September 20, 2025
Chilmark, Martha's Vineyard

Jessica & Max

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Things To Do

Lucy Vincent Beach

Lucy Vincent Beach

Chilmark, MA 02535

This town beach is one of the most lauded on the island. During the summer months May-Sept, access is restricted to only Chilmark residents. Luckily if you are staying near the wedding venue up-island, you will have access to the beach with passes provided by your hotel, bnb, or house rental. (or ask the bride or groom)

Gay Head Lighthouse & Clay Cliffs

Gay Head Lighthouse & Clay Cliffs

Aquinnah Circle, Aquinnah, MA 02535

Enjoy a magnificent view of the eroding clay cliffs off the western end of the island. Walk up to the overlook near the lighthouse, or trek down to the beach and walk to their base.

Oak Bluffs

Oak Bluffs

Oak Bluffs, MA

A nice mix of sea-side town and rich history. Check out the famous gingerbread houses and a walk down Circuit and Seaview aves.

Edgartown

Edgartown

Edgartown, MA

The "presidential" town. The closest thing to hustle and bustle, enjoy walking around downtown and enjoying waterside dinner and drinks. Or take a quick journey down to Katama Beach.

Menemsha Beach

Menemsha Beach

Basin Road, Chilmark, MA 02535

One of the best spots for an up-island sunset! Grab a casual seafood dinner to go at the adjacent Larsen's Fish Market or Menemsha Fish Market and take in the view.

Flying Horses Carousel

Flying Horses Carousel

15 Lake Avenue, Oak Bluffs, MA 02557

America's Oldest Carousel! Located in the heart of Oak Bluffs - if you grab the brass ring, you win a free ride!

Chappaquiddick Island

Edgartown, MA 02539

Highly recommended secluded part of the island away from tourists. Take the ~3 minute ferry from Edgartown (vehicle okay) and enjoy the tranquility. Check out the Japanese Gardens, Wasque Point, or take an offroading vehicle on the dunes up to Cape Poge.

Long Point Beach

Long Point Beach

Use Google Maps/Ask us,

Max's favorite place on Earth. Drive through a couple miles of dirt roads through the woods to access the wonderfully maintained, south shore beach. Home of the best surf in the island, Max loves it so much he's even come to the beach during two hurricanes! If the rough ocean isn't for you, enjoy the warmer, calmer, inland ponds. Off season access is a bit tricky/not straightforward, ask us for directions.

Mad Martha's Homemade Ice Cream

Mad Martha's Homemade Ice Cream

12 Circuit Avenue, Oak Bluffs, MA 02557

Our recommendation for island ice cream shop. Locations in Vineyard Haven, Oak Bluffs, and Edgartown. We recommend the OG Black Raspberry, or (Max's Favorite) the Sinful Chocolate.

Artists/Shops

Artists/Shops

The Vineyard is home to many small-scale artists, shops, eateries, landmarks, and adventures. Please contact us if you're looking for further recommendations - from our favorite pottery shop to lobster roll, we can hook you up with whatever you're after

For all the days along the way
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