Best Art Gallery: Granary Gallery

636 Old County Road, West Tisbury, 508-693-0455, granarygallery.com

Runner-up: Michael Blanchard Inspirational Photography/The Crossroads Gallery

93 Dukes County Avenue, Oak Bluffs, 617-448-3934, blanchardphotomv.com

At the Granary Gallery, lovers of art can view iconic Thomas Hart Benton pieces next to contemporary icons such as Cindy Kane and Kib Bramhall – both inside the red barn or outside in the courtyard. The Crossroads Gallery is home to Michael Blanchard’s beautiful photos captured around the Island.

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

147 Edgartown–West Tisbury Road, Edgartown, 508-627-3909, coopsbaitandtackle.com

Runner-up: Dick’s Bait & Tackle

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


When the stripers start running, fishermen head straight to Coop’s. Gear and bait is sold, of course, but the latest fishing reports, friendly service, and Coop’s legendary advice are offered freely. Tight-lipped anglers make no secret of another of their favorite spots: Dick’s Bait & Tackle.

Best Children’s Clothing: Basics Clothing Company

24 Circuit Avenue, Oak Bluffs, 508-693-8819, basicsandeastaway.company.site


Runner-up: Rainy Day

66 Main Street, Vineyard Haven, 508-693-1830, rainydaymv.com

Pink tulle dresses, denim overalls, shorts and T-shirts with sharks and bears and cats on them – Basics stocks the latest adorable styles from Carter’s, OshKosh B’Gosh, and more faster than the kiddos can outgrow them. Rainy Day offers the latest patterned pajamas and raincoats 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, 508-627-8366, flowersbydonaromas.com



Morrice Florist flowers live up to the hype. Whether it’s a single stem or a showstopping arrangement, every flower sold at Emily Coulter’s shop is breathtaking and unique. Donaroma’s has beautiful bouquets for all budgets.

Best Furniture/Home Goods Store: LeRoux at Home

62 Main Street, Vineyard Haven, 508-693-0030, lerouxkitchen.com

Runner-up: Vineyard Decorators

35 Airport Road, West Tisbury, 508-693-9197, vineyarddecorators.com

In need of a new measuring cup, curtains, or a bedspread? LeRoux’s three-level store has it all, and maybe even a kitchen doodad or two that you didn’t even know you needed. At Vineyard Decorators, the helpful staff can help pick the perfect piece of furniture.

Best Garden Center/Nursery: Donaroma’s

270 Upper Main Street, Edgartown, 508-627-3036, donaromas.com


Runner-up: Jardin Mahoney’s Garden Center

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

Donaroma’s impressive roadside displays only hint at the splendor that lies beyond. The greenhouse store is a wonderland of artfully arranged bonsai, indoor plants, and decorations. Outside, you’ll find everything you need to create your dream garden. Jardin Mahoney’s has a healthy, vibrant selection.

Best Gift Shop: Rainy Day


66 Main Street, Vineyard Haven, 508-693-1830, rainydaymv.com

Runner-up: C’est La Vie


51 Circuit Avenue, Oak Bluffs, 508-693-6181, facebook.com/cestlaviemv


Rainy Day offers hundreds of options when it comes to buying yourself or your friend a just-because present. Think: Island-inspired drinking glasses, horse puzzles, sea glass earrings, and the best selection of birthday cards on Martha’s Vineyard. At C’est La Vie, even if you’re “just browsing” you probably won’t end up leaving empty handed.

Best Hardware Store: Granite

242 Edgartown–Vineyard Haven Road, Edgartown, 508-627-3232, granitestores.com

Runner-up: Shirley’s Hardware

374 State Road, Vineyard Haven, 508-693-3070, stores.truevalue.com/ma/vineyard-haven/3261

Did months stuck in your house have you side-eyeing those rickety steps and that withering paint job? Granite is a one-stop DIY emporium of tools, stains, putties, and housewares perfect for whatever’s on your to-do list. Shirley’s keeps homes humming six days a week. (On Sundays, even home improvement heroes deserve a rest.)

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

For more than fifty years, CB Stark Jewelers has been crafting pieces that lovers of MV near and far can rock, such as a Classic Island Tie bracelet or one of the lighthouses in charm form. At Claudia you’ll find a curated selection of jewelers, including Island artisans and well-known luxury brands.

Best Men’s Clothing: 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


Whether you’re headed to the beach, the skate park, the disc golf course, or hitting the towns, the Green Room has you covered. Brands like Barbour, Patagonia, North Face, and O’Neill hit that Vineyard style sweet spot: comfortable and cool. Basics also stocks many favorite Island brands and looks.

Best New Store/Business: Salt Rock Chocolate Co.

508-449-0708, saltrockchocolate.com

Runner-up: Juniper

18 North Summer Street (in the courthouse parking lot), Edgartown, 508-939-4098, junipermv.com

Devotees of Chilmark Chocolates flocked to Salt Rock Chocolate Co. and were not disappointed. The Island’s newest chocolate company was started by Ali and Sarah Flanders, two sisters whose business was born out of the desire to keep the longtime Island chocolatier’s recipes alive. Juniper sells flowers, gifts, and you guessed it – chocolates.

Best Pharmacy: Leslie’s Drug Store

65 Main Street, Vineyard Haven, 508-693-1010, lesliesdrugstore.com

Runner-up: Conroy Apothecary

459 State Road, West Tisbury, 508-693-7070, conroyapothecary.net


Leslie’s Drug Store isn’t just a pharmacy; it’s a Vineyard institution. Late last year, when it looked as if the Main Street staple might have to close its doors for good, loyal customers and investors rallied to save it. Conroy’s customers are similarly devoted, and the selection is hard to beat.

Best Shoes: Green Room

65 Main Street, Unit 13, Vineyard Haven, 508-693-6888, greenroommv.com

Runner-up: Basics Clothing Company

24 Circuit Avenue, Oak Bluffs, 508-693-8819, basicsandeastaway.company.site


How much do Islanders love the Green Room’s selection of Frye, Dansko, Blundstone, Xtratuf, and Birkenstock? Enough that the Vineyard Haven mainstay recently opened another Main Street location dedicated entirely to shoes. Basics offers not just what you need, but also what you just plain want.

Best Women’s Clothing: 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


Remember real pants? Non-stretchy jeans? Fancy tops with buttons? The stylish folks at the Green Room do, and are on hand to cure you of your leggings and sweatshirts addiction. The fantastic and varied inventory will make the transition easier. Stop by Basics for even more cute dresses, shorts, and tunics.