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Do NOT Miss Chilmark Chocolates

Chilmark Chocolates is one of those places on the island that you just have to go. The chocolate is amazing – original recipes either handmade or hand-dipped. And the atmosphere is inspired and inspiring.

The shop, located in the heart of Chilmark, is staffed by disabled people. With equipment that has been adapted for ease of use and specific abilities, the entire staff fills the store with must-have truffles, chocolate covered fruit and more. Delighting our taste buds while raising awareness – what more could we ask for?

While the Butter Crunch is a longtime favorite, Chilmark Chocolates dips seasonal and local treats in their chocolate (think strawberries, blueberries and cranberries) for tastes that are truly Vineyard grown.

Village Spotlight: Vineyard Haven

The village of Vineyard Haven, located in the town of Tisbury, is the main port for Martha’s Vineyard. The harbor is the year-round home to the island ferries run by The Steamship Authority (passengers, cars and freight) and the New England Fast Ferry (passengers only), and it is filled with private and charter sail boats throughout the year and especially each summer. Once you step ashore, some of the best the Vineyard has to offer is within walking distance.

The famous Black Dog Tavern, bakery and retail shops stand steps away from the ferry, and most visitors mark their summer visits by purchasing their annual Black Dog t-shirts. Sitting on the porch at the tavern happily devouring your lobster dinner remains a highlight and is always worth the wait. No reservations accepted, but it’s a joy to sit on the small beach and watch the harbor while you wait for your name to be called.

Bike and car rentals are close by to help you get around, but you don’t even need them to explore Vineyard Haven’s Main Street. This picturesque, shopping extravaganza of a street boasts unique boutique style shops filled with clothes, cool stuff, books and art. Some of our favorite spots are The Green Room (men and women’s clothing), Bunch of Grapes (one of the greatest bookstores ever) and Rainy Day (literally filled with too many fantastic items to list here). Art galleries abound and showcased artists often capture the spirit and beauty of the island.

Vineyard Haven offers excellent dining (Le Grenier) and quick eats (ArtCliff)…and plenty of ice cream (Mad Martha’s) – just to name a few hot spots. The Mansion House hotel, spa, health club and restaurant (Zephrus) stands right on the corner of Main and State Road giving guests full service inside and total access to the town. If it rains, duck into the Capawock movie theater, a refreshing change from the multi-plex, or find the Vineyard Playhouse which features a summer packed with world-renowned plays and actors in a unique Vineyard setting.

And if you have time, wander just a block or two past Main Street, up away from the harbor. You’ll find the a beautiful, seaside, New England town – white clapboard homes, lush gardens and tons of character.

Martha’s Vineyard Vacation Rental: Chilmark Escape

Nestled in Chilmark, this gem is a perfect family retreat. Here are my top 3 highlights:

1. Luxury. From top to bottom. From the construction to the woodwork to the appliances to the furniture to the Jacuzzi in the Master Bedroom…The whole house is beautiful and full of understated, yet high-end, charm.

2. Get Outside. With a spacious backyard, rolling meadows, stone walls, walking trails and tennis court access, how can you not? Also, two of the most cherished beaches on the island are close by, Lucy Vincent and Squibnocket.

3. The Kitchen. It begs for island dinners that take all day to make and moments to devour or take minutes to make and hours to linger over. The warmth of the custom cabinetry and the overall coziness of the room almost guarantees that whatever you create will taste incredible – lobster, corn on the cob and strawberry rhubarb pie anyone?