Best Bookstore: Bunch of Grapes Bookstore
35 Main Street, Vineyard Haven, 508-693-2291, bunchofgrapes.com
Runner-up: Edgartown Books
44 Main Street, Edgartown, 508-627-8463, edgartownbooks.com
Don’t miss a chance to peruse the rows at the Bunch of Grapes, where you’re sure to find a variety of classics by Island authors as well as popular best sellers. (Plus, you may even spot some of the authors themselves.) Edgartown Books has two stocked floors, plus a secluded backyard café for thumbing through your newest read.
Best Art Gallery: Granary Gallery
636 Old County Road, West Tisbury, 508-693-0455, granarygallery.com
Runner-up: Eisenhauer Gallery
38 North Water Street, Edgartown, 508-627-7003, eisenhauergallery.com
You can’t help but be intrigued by the iconic red barn that houses the Granary Gallery. The outside showcases sculptures and antiques, while inside is a diverse mix of mediums by artists near and far. In the heart of Edgartown, the Eisenhauer Gallery’s unique collection ranges from paintings to jewelry.
Best Bait and Tackle Shop: Dick’s Bait & Tackle
108 New York Avenue, Oak Bluffs, 508-693-7669
Runner-up: Coop’s Bait & Tackle
147 Edgartown-West Tisbury Road, Edgartown, 508-627-3909, coopsbaitandtackle.com
From reel servicing and scallop knives to live bait and squid jigs, Dick’s Bait & Tackle is the go-to store for avid fishermen. At Coop’s Bait & Tackle, be sure to catch up on the latest lowdown regarding weather, tides, and maybe a hint at a fishing hot spot.
Best Children’s Clothing: Basics Clothing Company
24 Circuit Avenue, Oak Bluffs, 508-693-8819, basicsclothingcompany.com
Runner-up: Rainy Day
66 Main Street, Vineyard Haven, 508-693-1830, rainydaymv.com
In the new and improved Basics store, parents and tots can search through a large selection of children’s styles, ranging from fluorescent rain boots to adorable dresses and button-ups for special occasions. Over at Rainy Day, an entire area is dedicated to the latest baby fashions.
Best Flowers: Morrice Florist
149 State Road, Vineyard Haven, 508-693-0392, morriceflorist.com
Runner-up: Flowers by Donaroma’s
270 Upper Main Street, Edgartown, 508-627-8366, flowersbydonaromas.com
Now in its seventy-fifth year, Morrice Florist is still dedicated to creating cheerful get-well bouquets or that particular floral arrangement that says you care. At Flowers by Donaroma’s, the florists take advantage of whichever blooms are in season to create striking arrangements.
Best Garden Center/Nursery: Jardin Mahoney
45 Edgartown–Vineyard Haven Road, Oak Bluffs, 508-693-3511, jardinmahoney.com
Runner-up: Donaroma’s Nursery & Landscape Services
270 Upper Main Street, Edgartown, 508-627-3036, donaromas.com
If it’s time to transform your landscape, you can’t go wrong with a trip to Jardin Mahoney. From ornamental grasses to hydrangeas and certified organic herb and veggie starters, the garden center has it all. At Donaroma’s, get advice for the best plant combinations and be the envy of the neighborhood.
Best Gift Shop: Rainy Day
66 Main Street, Vineyard Haven, 508-693-1830, rainydaymv.com
Runner-up: Sanctuary
42 Circuit Avenue, Oak Bluffs, 508-693-9600, thelifedivine.com
When shopping for gifts, Rainy Day has a little something for everyone: a festive rain slicker for a little one, an Island-themed tablecloth for the hostess, kitchenware for the bride and groom … and maybe a fragrant candle for yourself! Greeting cards, wrapping paper, and ribbon make it a one-stop shop. Sanctuary specializes in inspirational gifts with meaningful messages to soothe the soul.
Best Hardware Store: Shirley’s Hardware
374 State Road, Vineyard Haven, 508-693-3070
Runner-up: Edgartown Hardware
61 Edgartown–West Tisbury Road, Edgartown, 508-627-4338, edgartownhardware.com
Shirley’s is more than just your local hardware store; it’s a Vineyard staple with seasonal necessities from snow shovels and ice melt to grill supplies and citronella candles. Edgartown Hardware has more than 20,000 items in stock and knowledgeable staff on hand to make your do-it-yourself project a breeze.
Best Home Goods Store: LeRoux at Home
62 Main Street, Vineyard Haven, 508-693-0030, lerouxkitchen.com
Runner-up: Rainy Day
66 Main Street, Vineyard Haven, 508-693-1830, rainydaymv.com
With the latest cookware, baking tins, linens, towels, and more, LeRoux is the Island’s one-stop shop for home furnishings both basic and extravagant. For a curated, Island-themed collection, take a walk down the street to runner-up Rainy Day for select pieces to tie it all together.
Best Men’s Clothing: Green Room
71 Main Street, Vineyard Haven, 508-693-6888, vineyardsurf.com
Runner-up: Basics Clothing Company
24 Circuit Avenue, Oak Bluffs, 508-693-8819, basicsclothingcompany.com
Fashionable men need look no further than the Green Room. Whether a surfer, skater, businessman, or all of the above, the Vineyard Haven store has something in stock to suit your style. The hardest decision you’ll have to make is how much you want to splurge. At Basics, grab styles from DKNY, Nautica, and Lucasini to ramp up your wardrobe.
Best Shoes: Green Room
71 Main Street, Vineyard Haven, 508-693-6888, vineyardsurf.com
Runner-up: Basics Clothing Company
24 Circuit Avenue, Oak Bluffs, 508-693-8819, basicsclothingcompany.com
Are your soles feeling worn down and tired? Head over to the Green Room for some retail therapy, where you’ll find sneakers, sandals, Frye boots, and more to keep both the ladies and gentlemen happy. In Oak Bluffs, enjoy Basics’ bigger, better store, which now has an entire section devoted to shoes.
Best Jeweler: CB Stark Jewelers
53A Main Street, Vineyard Haven, 508-693-2284
10 Main Street, Edgartown, 508-627-1260, cbstark.com
Runner-up: Claudia
51 Main Street, Edgartown, 508-627-8306
34 Main Street, Vineyard Haven, 508-693-5465, claudiamv.com
CB Stark offers a variety of Island-inspired collections that keep customers coming back for more. Try the popular Island Ties, Vineyard Charms, Grapes, or even the Jaws-inspired pieces. Claudia stocks treasures from local artisans and nationally recognized jewelers, as well as a selection of perfumes and hair accessories.
Best Pharmacy: Leslie’s Drug Store
65 Main Street, Vineyard Haven, 508-693-1010
Runner-up: Conroy Apothecary
459 State Road, West Tisbury, 508-693-7070
82 Pennacook Avenue, Oak Bluffs, 508-696-0700
Sure, you could just pick up your prescription and head for the door. Or, you could take your time exploring the aisles of Leslie’s Drug Store, where you’ll find the best skin, hair, or nail care products on the market, from the likes of Badger, Sally Hansen, and L’Oreal. Conroy’s boasts a similarly great selection, and has locations both up-Island and down.
Best Women’s Clothing: Green Room
71 Main Street, Vineyard Haven, 508-693-6888, vineyardsurf.com
Runner-up: Basics Clothing Company
24 Circuit Avenue, Oak Bluffs, 508-693-8819, basicsclothingcompany.com
With two floors of the hottest brands at competitive prices (Free People, Patagonia, Paige, and BCBG, to name a few), the Green Room is a tried-and-true Island fashion destination. Over at Basics, pick up a colorful scarf, the perfect clutch, or a sophisticated jacket to complete your look.
