Best Art Gallery: The 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
Nestled in a charming red barn, The Granary Gallery holds the title of Martha’s Vineyard’s oldest and largest art gallery – and the best one too. Featherstone Center for the Arts hosts thought-provoking exhibitions in their Art Barn.
Best Bait & 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
Head to Dick’s Bait & Tackle for all your fishing needs and leave prepared for just about any kind of angling adventure. Cooper Gilkes, owner of Coop’s Bait & Tackle, can also get you geared up at his shop.
Best Children’s Clothing: Basics Clothing Company
24 Circuit Avenue, Oak Bluffs, 508-693-8819, basicsandeastaway.company.site
Runner-up: Chicken Alley Thrift Shop
38 Lagoon Pond Road, Vineyard Haven, chickenalley.org
The aptly named Basics Clothing Company is a family-owned store that has all types of children’s essentials, from outerwear to shoes. Surprises are always in store at Chicken Alley. Stop by to find deals on pre-loved kids’ apparel.
Best Flowers: Morrice Florist
149 State Road, Vineyard Haven, 508-693-0392, morriceflorist.com
Runner-up: Flowers by Donaroma’s/Aubrey Maria Designs/Juniper
270 Upper Main Street, Edgartown, 508-627-8366, flowersbydonaromas.com
Morrice Florist is the Vineyard’s oldest flower shop. The year-round destination offers exquisite floral arrangements, lush plants, and a curated selection of gifts and homewares. Flowers by Donaroma’s/Aubrey Maria Designs/Juniper is a multi-hyphenate specializing in bouquets that capture the Island’s natural beauty.
Best Garden Center/Nursery: Jardin Mahoney’s Garden Center
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
Jardin Mahoney’s Garden Center has an extensive selection of plants, trees, shrubs, and gardening supplies. Perhaps their most valuable product is their expertise in all things green. Donaroma’s is a one-stop destination for your gardening needs too.
Best Gift Shop: Rainy Day
66 Main Street, Vineyard Haven, 508-693-1830
12 North Water Street, Edgartown, rainydaymv.com
Runner-up: Bunch of Grapes Bookstore
23 Main Street, Vineyard Haven, 508-693-2291, bunchofgrapes.indielite.org
If you need a gift to take home for a loved one, Rainy Day has shelves filled with home goods, Island-made products, and options for the kids. Bunch of Grapes offers an endless book selection along with postcards and gifts perfect for the reader in your life.
Best Hardware Store: Granite
242 Edgartown–Vineyard Haven Road, Edgartown, 508-627-3232, granitestores.com
Runner-up: Shirley’s True Value Hardware
374 State Road, Vineyard Haven, 508-693-3070, stores.truevalue.com/mavineyard-haven/3261
There’s no need for big-box stores on the Vineyard when we have reliable hardware stores such as Granite, which is fully stocked with school supplies, party essentials, tools, and more. Shirley’s is organized with shelves for all your home-project and job-site needs.

Best Furniture/Home Goods Store: Chicken Alley Thrift Shop
38 Lagoon Pond Road, Vineyard Haven, chickenalley.org
Runner-up: Vineyard Decorators
35 Airport Road, West Tisbury, 508-693-9197, vineyarddecorators.com
Chicken Alley Thrift Shop always has pre-loved furniture pieces on display as well as other home goods on offer at affordable prices. The best part? The proceeds go to Martha’s Vineyard Community Services. Vineyard Decorators has the largest in-house inventory of furniture on the Island.
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, claudia.jewelry
Along with a wide selection of fine jewelry, CB Stark Jewelers offers repairs and consultations with care. They also have unique finds you can only see on the Island. Claudia’s inventory includes pieces from artisan jewelers and designers as well as accessories and perfume.
Best Men’s Clothing: The Green Room
71 Main Street, Vineyard Haven, 508-693-6888, greenroommv.com
Runner-up: Brickman’s of Martha’s Vineyard
8 Main Street, Vineyard Haven, 508-693-0047, brickmans.com
The Green Room has been a menswear staple for thirty years. Whether it’s outerwear for your next Island trek or a new pair of jeans, the store has got you covered. Brickman’s has been around since 1913 and offers high-quality clothing and accessories.

Best New Store/Business: Dune
9 Winter Street, Edgartown, 774-549-9304, dunemv.com
(TIE) – Runners-up: Adrift
30 Main Street, Unit B, Vineyard Haven, 508-527-1113, mvyadrift.com
The Sunny Side MV
18 Main Street, Vineyard Haven, thesunnysidemv.com
Dune is the new spot to go to for upscale menswear. From casual to formal, you’ll find shirts, pants, belts, and footwear. Adrift’s mantra is all about giving back, as part of their profits support Island nonprofits. At The Sunny Side MV, women’s clothing comes in fun styles and designs.
Best Pharmacy: Conroy Apothecary
459 State Road, West Tisbury, 508-693-7070, conroy-apothecary.com
Runner-up: Stop & Shop Pharmacy
245 Edgartown–Vineyard Haven Road, Edgartown, 508-627-5107, pharmacy.stopandshop.com
If you’re looking for a spot where you can pick up a prescription as well as purchase toothpaste and find a birthday card, Conroy’s is the place. Stop & Shop Pharmacy is brimming with medicine, snacks, diapers, and magazines (including this one!).
Best Shoes: The Green Room
65 Main Street, Unit 13, Vineyard Haven, 508-693-6888 ext. 15, greenroommv.com
Runner-up: Brickman’s of Martha’s Vineyard
8 Main Street, Vineyard Haven, 508-693-0047, brickmans.com
Whether you are in the market for a new pair of sandals, sneakers, or boots, The Green Room’s Shoe Store – just a few doors down from its parent store – is your one-stop shop. Also on Vineyard Haven’s Main Street, Brickman’s offers a variety of everyday shoes.
Best Women’s Clothing: The Green Room
71 Main Street, Vineyard Haven, 508-693-6888, greenroommv.com
Runner-up: Basics Clothing Company
24 Circuit Avenue, Oak Bluffs, 508-693-8819, basicsandeastaway.company.site
From colorful tops and comfortable dresses to surf and skate options, The Green Room has an outfit for every occasion. At Basics Clothing Company, find the essentials that women need and maybe some extras that they want.