Best Art Gallery: Granary Gallery

636 Old County Road, West Tisbury, 508-693-0455,

Runner-up: Featherstone Center for the Arts

30 Featherstone Lane, Oak Bluffs, 508-693-1850,

Featuring works by iconic Island artists, such as Alfred Eisenstaedt, Lew French, and Thomas Hart Benton, the Granary Gallery should be your first stop on any Vineyard gallery tour. With its community exhibits and classes in a range of mediums, Featherstone Center for the Arts brings art to the people.

Best Bait and Tackle Shop: Coop’s Bait & Tackle

147 Edgartown–West Tisbury Road, Edgartown, 508-627-3909

Runner-up: Dick’s Bait & Tackle

108 New York Avenue, Oak Bluffs, 508-693-7669

Cooper Gilkes of Coop’s Bait & Tackle is a bona fide Vineyard celebrity known for his fishing know-how. No wonder anglers prefer to get their bait from the renowned sportsman. Dick’s Bait & Tackle will outfit you for nearly any outdoors endeavor, from deep-sea fishing to clamming.

Best Children’s Clothing: Basics Clothing Company

24 Circuit Avenue, Oak Bluffs, 508-693-8819,

Runner-up: Rainy Day

66 Main Street, Vineyard Haven, 508-693-1830, 12 North Water Street, Edgartown,

Basics Clothing Company sells the types of clothes your toddler actually wants to wear, from brands such as Cutie Patootie, Levi’s, and Crocs. At Rainy Day, whimsical flair meets practical comfort.

Best Flowers: Morrice Florist 

149 State Road, Vineyard Haven, 508-693-0392,

Runner-up: Flowers by Donaroma’s

270 Upper Main Street, Edgartown, 508-627-8366,

Whether you’re looking for showstopping blooms to fill out your wedding ceremony or an elegant dinner table bouquet, Morrice Florist combines expertise with fresh, high-quality flora. Flowers by Donaroma’s offers stunning arrangements for any occasion.

Best Furniture/Home Goods Store: Vineyard Decorators

35 Airport Road, West Tisbury, 508-693-9197,

Runner-up: Chicken Alley Thrift Shop

38 Lagoon Pond Road, Vineyard Haven,

Vineyard Decorators has the largest in-house stock of furniture on the Island, plus white-glove delivery so you don’t have to lift a finger (or take a ferry). Chicken Alley Thrift Shop boasts eclectic home offerings at affordable prices – plus, all proceeds go to Martha’s Vineyard Community Services.

Best Garden Center/Nursery: Jardin Mahoney’s Garden Center

45 Edgartown–Vineyard Haven Road, Oak Bluffs, 508-693-3511,

Runner-up: Donaroma’s

270 Upper Main Street, Edgartown, 508-627-3036,

Whether or not you have a green thumb, Jardin Mahoney’s Garden Center has the soil, seed, and foliage you need to cultivate your ideal garden. At Donaroma’s, luxury greenery, trees, and shrubs can help your landscape reach new heights.

Best Gift Shop: Rainy Day

66 Main Street, Vineyard Haven, 508-693-1830: 12 North Water Street, Edgartown,

Runner-up: The Beach House

30 Main Street, Vineyard Haven, 508-693-6091,

Rainy Day is a perennial winner in this category, and when you take a look at their two stores packed with wall-to-wall goodies, you’ll know why. The Beach House supplies unique, locally sourced housewares and linens – perfect gifts for a host or for yourself.

Best Hardware Store: Granite

242 Edgartown–Vineyard Haven Road, Edgartown, 508-627-3232,

Runner-up: Shirley’s True Value Hardware

374 State Road, Vineyard Haven, 508-693-3070,

The bigger-on-the-inside hardware store is an Island staple for a reason. If you need something, Granite probably has it somewhere within its labyrinthine aisles. Shirley’s provides dependable service and a wide range of goods to Island DIY-ers and craftsmen.

Best Jeweler: CB Stark Jewelers

53A Main Street, Vineyard Haven, 508-693-2284;  10 Main Street, Edgartown, 508-627-1260,

Runner-up: Claudia

51 Main Street, Edgartown, 508-627-8306  34 Main Street, Vineyard Haven, 508-693-5465,

It’s a charmed life at CB Stark! In addition to helping you shop for unique and classic accessories, such as their beloved Island charms, the jewelers can also appraise, clean, and repair your pieces with care. If you’re in need of retail therapy or a finely crafted accessory, Claudia has the goods. 

Best Men’s Clothing: The Green Room

71 Main Street, Vineyard Haven, 508-693-6888,

Runner-up: Brickman’s of Martha’s Vineyard

8 Main Street, Vineyard Haven, 508-693-0047,

Whether it’s outerwear from Patagonia, a button-down from Toad & Co, or a fresh new pair of jeans from Citizens of Humanity, the Green Room has got your clothing needs covered. Brickman’s has low prices and top-notch quality when it comes to everyday threads. 

Best New Store/Business: Respoke

8 Main Street, Edgartown, 508-939-3641,

Runner-up: Black Joy Food Love

125 Seaview Avenue, Oak Bluffs, 240-481-8146,

Respoke’s business model of repurposing fine silk scarves into accessories and espadrilles has certainly resonated with the Vineyard crowd: the downtown Edgartown storefront has been crowned Best New Store/Business. Runner-up Black Joy Food Love, a catering company, believes in nourishing the body through high-quality health food.

Best Pharmacy: Conroy Apothecary

459 State Road, West Tisbury, 508-693-7070,

Runner-up: Leslie’s Drug Store

65 Main Street, Vineyard Haven, 508-693-1010,

At Conroy Apothecary, you’re sure to encounter a friendly face, whether you’re stopping by the drive-through, seeking expert advice from the knowledgeable staff, or perusing the well-appointed store. Pop into Leslie’s Drug Store when you need band-aids, cold medicine, or a quick souvenir.

Best Shoes: The Green Room

65 Main Street, Unit 13, Vineyard Haven, 508-693-6888 x15,

Runner-up: Basics Clothing Company

24 Circuit Avenue, Oak Bluffs, 508-693-8819,

In the market for a new pair of running shoes or rain boots? Or maybe slippers and sandals? The Green Room’s Shoe Store – two doors down from their main location – has it all and more. Basics stocks much-loved brands for everyone in the family. 

Best Women’s Clothing: The Green Room

71 Main Street, Vineyard Haven, 508-693-6888,

Runner-up: Basics Clothing Company

24 Circuit Avenue, Oak Bluffs, 508-693-8819,

Vineyarders in search of a good sundress and denim jacket combination need look no further than the Green Room, which stocks all sorts of Island-favorite attire. Basics Clothing Company sells trendy, elevated basics (and more) that are suitable for any season.