Best Art Gallery: Granary Gallery
636 Old County Road, West Tisbury, 508-693-0455, granarygallery.com
Runner-up: Featherstone Center for the Arts
30 Featherstone Lane, Oak Bluffs, 508-693-1850, featherstoneart.org
You don’t have to make a sojourn to SoHo to visit an elite art gallery. Granary Gallery, the Island’s oldest and largest, features the work of both up-and-comers and notables like Thomas Hart Benton and Alfred Eisenstaedt. Featherstone emphasizes education and has two state-of-the-art galleries.
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
Rods, reels, plugs, and jigs: Dick’s Bait & Tackle has everything you need to try your luck in Vineyard waters, including a whole bunch of dead squid. Of course, the real reason customers keep coming back probably has a lot to do with the staff’s expert tips. Coop’s Bait & Tackle has it all, including a wide selection of fly-fishing gear.
Best Children’s Clothing: Basics Clothing Company
24 Circuit Avenue, Oak Bluffs, 508-693-8819, facebook.com/basicsandeastaway
Runner-up: Rainy Day
66 Main Street, Vineyard Haven, 508-693-1830, rainydaymv.com
On the Vineyard, looking like a Basics kid is a good thing. It means you’re probably decked out in the latest from Carter’s and OshKosh B’gosh, maybe rocking a sweet leopard vest or a cool dinosaur T-shirt. Rainy Day caters to the younger set with creative onesies and the latest from Hatley.
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, 508-627-3036, donaromas.com
Morrice Florist prepares swoon-worthy arrangements for weddings and special occasions, but you don’t need to wait for a big event to enjoy their work. The talented crew also stocks houseplants, gift items, and grab-and-go bouquets. Flowers by Donaroma’s caters to your budget and palette.
Best Furniture/Home Goods Store: Vineyard Decorators
35 Airport Road, West Tisbury, 508-693-9197, vineyarddecorators.com
Runner-up: LeRoux at Home
62 Main Street, Vineyard Haven, 508-693-0030, lerouxkitchen.com
Reports of the need to go furniture shopping off-Island have been greatly exaggerated, and in fact debunked. Vineyard Decorators is a terrific one-stop home furnishing shop, complete with bedroom sets, sofas, and outdoor furniture. LeRoux is the place to go for rugs, draperies, and bedding.
Best Garden Center/Nursery: Jardin Mahoney
45 Edgartown–Vineyard Haven Road, Oak Bluffs, 508-693-3511, jardinmahoneymv.com
Runner-up: Donaroma’s
270 Upper Main Street, Edgartown, 508-627-8366, donaromas.com
Whether you have a black or a green thumb, you’ll find everything you need at Jardin Mahoney, from well-cared-for annuals and perennials to a large selection of tools. Donaroma’s boasts numerous greenhouses with fresh flowers, bonsai trees, and exotic plants.
Best Gift Shop: Rainy Day
66 Main Street, Vineyard Haven, 508-693-1830, rainydaymv.com
Runner-up: Alley’s General Store
1045 State Road, West Tisbury, 508-693-0088, vineyardtrust.org
Picking the perfect gift is easy at Rainy Day, where you will find a little something for everyone, from sweet-smelling candles to serving plates, novelty socks, and Island-made goods. At Alley’s, explore aisles of trinkets, toys, and clothes.
Best Hardware Store: Shirley’s Hardware
374 State Road, Vineyard Haven, 508-693-3070, shirleyshardwaremv.com
Runner-up: Granite
242 Edgartown–Vineyard Haven Road, Edgartown, 508-627-3232
A trip to the hardware store usually means you have hours of hard work in store. Shirley’s Hardware makes the lead-up easy. Tools, stains, putties, housewares, and gardening supplies are always in stock and easy to find. Granite offers a vast assortment of bits, bobs, and necessities at fair prices.
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
The name CB Stark is synonymous with sophisticated, high-end, Island-inspired jewelry. Fans love the earrings, watches, cufflinks, and, above all, Vineyard charms. Claudia showcases a large selection of national and international designers, plus perfumes and accessories.
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, facebook.com/basicsandeastaway
The Vineyard man has a certain look. If it’s a good look, he probably got it at the Green Room. Selections of plaids, button downs, T-shirts, hats, and jeans aren’t chosen just for comfort but for style. Basics offers many of the same brands in the heart of Oak Bluffs.
Best New Store/Business: Tisbury Toy Box
Tisbury Marketplace, 79 Beach Road, Vineyard Haven, 508-693-8182, facebook.com/TisburyToyBoxMV
Runner-up: North Tisbury Farm & Market
632 State Road, West Tisbury, 508-696-4664, northtisburyfarm.com
The halcyon days of the independent toy store are alive and well on the Vineyard, thanks to fun lovers Kate and Alex Salop who purchased The Toy Box in 2018 and rechristened it the Tisbury Toy Box. North Tisbury Farm & Market ably fills the void left by Fiddlehead Farm.
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, conroyapothecary.net
Got a question about cough syrups? Need a second opinion on sunscreens? You’ll find everything you need at Leslie’s Drug Store, in the heart of Vineyard Haven, including beauty and beach supplies and helpful advice. Conroy Apothecary provides friendly service in two convenient locations.
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, facebook.com/basicsandeastaway
You won’t find shiny stilettos at the Green Room. Here, Frye boots equals fancy, and quality and durability are the main concerns. Top-selling brands include Blundstone, Birkenstock, Hunter, and OluKai. At Basics, shop for Reefs, Dansko, and, yup, more Fryes.
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, facebook.com/basicsandeastaway
For twenty-five years, ladies have been zhuzhing their jean collections, perfecting their pullover game, and stepping up their sundress styles at the Green Room with brands like CP Shades, Free People, Paige, and Patagonia. Basics stocks Helly Hansen, Tribal, and Columbia, among others.
