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Chilmark Chocolates
19 State Rd, Chilmark, MA 02535

This tiny chocolate shop is closed Monday through Wednesday, but the rest of the week it's absolutely packed withMore people. With good reason, too: these chocolates are famous. The store can only accomodate about ten people at a time, so customers often line up around the building to have their shot at these great chocolates. 

The store employs many mentally handicapped citizens who are trained to use specially modified machinery to suit their needs. Chilmark Chocolates also sponsors an island nonprofit organization each month. Your purchases and donations go to benefit their workers as well as the monthly organization of their choosing.

New Moon Magick & Enchanted Chocolates
4 Chapman Ave, Oak Bluffs, MA 02568

Mystical candles and healing stones jostle for position with local antiques, vintage jewelery and vintage linens. IfMore you can resist these things, you might have more difficulty with the lure of "enchanted" chocolates, made with 70 percent cacao.

New Moon Magick - Enchanted Chocolates is also a Gold Winner from Martha's Vineyard Candy Shops in Cape Cod Life's Readers Choice Awards.

Not Your Sugar Mama’s Chocolate Factory & Cafe
79 Beach Rd # 15, Vineyard Haven, MA 02568
Henry's
131 N Water St, Edgartown, MA 02539
Henry's is located inside the Harborview Hotel and is a casual yet elegant spot for drinks and dining with a view ofMore Edgartown Harbor. All menu items are made in-house, including their clam chowder and their house-cured meats and pate. Wine, beer, cocktails and martinis are all served. Specialty martinis include the Mint Chocolate Chip Martini and the White Chocolate Espresso Martini. Pre-fix menus are served during off-season. Free Wi-Fi is available.
Zephrus
9 Main St, Vineyard Haven, MA 02568
Zephrus offers lunch and dinner daily. Menu highlights include the green machine salad, BLT, turkey burger Reuben, freshMore fish and chips, crispy fried calamari, open-faced tuna melt and molten chocolate cake. It also offers a selection of wines as well as bottled and draft beers.
Good Ship Lollipop
61 Circuit Ave, Oak Bluffs, MA 02557
Located on Circuit Avenue since 2005, the Good Ship Lollipop is a custom confectionary. Old-fashioned candies, homemadeMore chocolates and dietary specific treats are some of the offerings in the shop. Custom orders for events and weddings can also be accomodated.
Black Sheep
18 N Summer St, Edgartown, MA 02539
Black Sheep sells a variety of artisanal cheese, chocolates, smoked meats, olives and caviar, among other items. CheeseMore types offered include Georgia Gouda, Oregon Blue, Maplebrook Farm Handmade Mozzarella, Truffle Tremor, and other types of goat and cow milk.
7a Foods
1045 State Rd, Vineyard Haven, MA 02568
7a Foods is a sandwich shop and grocery boutique. It offers prepared and made-to-order foods made from locally-grown andMore produced ingredients. Prepared foods include sauces, oils, crackers, chips and chocolates. Made-to-order items include breakfast sandwiches, bagels, oatmeal, pulled pork, chicken salad and eggplant sandwiches, hot dogs and more. It also sells baked goods, such as muffins, brownies and cakes. Ice cream, milk, coffee, tea, juice and soda are also sold.
Ben & Bill's Chocolate Emporium
20A Circuit Ave, Oak Bluffs, MA 02557
Ben & Bill's have created quite a following over the years for having some of the best and most flavorful varietiesMore of ice cream  on the island. The Emporium is filled with handmade candies, freshly made fudge, gelato and ice cream. There are benches outside where you can enjoy your goodies with your dog while watching the hustle and bustle of Circuit Avenue during the summer. 
Henley's Needlepoint and Fibers
44 Main St, Edgartown, MA 02539
Henley's Needlepoint is located in a white building situated just off the beaten path of Main Street in downtownMore Edgartown. The owners, John and Susan, are there in the shop most days, and are excited to cater both  to passing guests on tour buses and crafting mavens looking for tips and advice. Henley's offers not only the yarn, thread and other supplies, but also has handmade ornaments, patterns, stockings and slippers inspired by local Vineyard flavor.  It also offers finishing services for pillows, belts and other handmade items. Expert patterns and beginners' kits are available. Henley's works with local artists to photos into works of art rendered in needlepoint. You can join the Henleys and local crafting fans from 3pm - 5pm on Thursday afternoons for conversation, consultation and chocolate.