Best Bookstore: Bunch of Grapes

35 Main Street, Vineyard Haven, 508-693-2291, bunchofgrapes.com

Runner-up: Edgartown Books

44 Main Street, Edgartown, 508-627-8463, edgartownbooks.com

Looking for something to read by a local author? Or a national bestseller? (Or both?) Better book it to Bunch of Grapes, where the selection of Island titles is hefty and the sales staff is super knowledgeable. Edgartown Books has two floors of novels, cookbooks, and children’s tales, plus a café out back and rocking chairs on the front porch. Keep an eye out for signings at both stores.

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

It doesn’t matter if you just need to make a quick stop for bait or are looking to book a full-service charter, Coop’s Bait & Tackle has absolutely everything you need to reel in a big one. The staff at Coop’s is always ready with expert fishing advice, and stays informed about weather, tides, and fishing regulations. Dick’s is a must-stop shop for the Island’s avid fishermen and beginners alike.

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

At Basics, the clothing selection is anything but. You’ll find party dresses, button-downs, overalls, tiny tunics, jeans, and mini accessories – clothing so cute we wish it came in adult sizes. Runner-up Rainy Day has got your little ones covered with coveted brands like Hatley and Southern Yankee. You’re bound to find an adorable outfit, with a cute little rain slicker to boot.

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

Don’t just stop and smell the roses. Stop and smell the tulips, hydrangeas, and delphiniums at Morrice Florist in Vineyard Haven. Check the website for a list of year-round workshops, where you can learn about different types of flowers and how to arrange them. Donaroma’s provides a range of services and beautiful bouquets for any occasion.

Best Garden Center/Nursery: Donaroma’s Nursery

271 Upper Main Street, Edgartown, 508-627-3036, donaromasnursery.com

Runner-up: Jardin Mahoney

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

From azaleas to zinnias, Mike and Janice Donaroma and their team have been enhancing Island landscapes for nearly forty years. Their services include garden design, hardscapes,
irrigation, lighting, floral design, maintenance, and more. Donaroma’s specializes in “Island style,” which combines organic materials and Vineyard-grown perennials. Fans of Jardin Mahoney appreciate the knowledgeable staff, quality products, and helpful advice.

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, mvpreservation.org

Cards, candles, carafes, home décor galore! If you want it, Rainy Day has it – and probably with an unexpected twist. Buying a gift is easy with so many options at hand (although choosing from so many options can be difficult). At Alley’s General Store you can pick up a gift while buying your milk, bread, boogie boards, and tools. True to its name, as a general rule, you can find almost anything.

Best Hardware: Shirley’s Hardware

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

Runner-up: Granite

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

Shirley’s Hardware still has everything you’re looking for, and they’re still making keys! It’s your one-stop shop for hammers, nails, laundry baskets, and grilling items. Runner-up Granite is well stocked with shelves of spray paint, clocks, rakes and...the list goes on (and on and on).

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

Good, better, best – that’s the philosophy behind LeRoux’s award-winning stocking strategy to ensure customers have a variety of choices. The Vineyard Haven store is chock full of everything you need, and plenty of items that you’ll covet. If it’s a chic home good, gift, or excellent greeting card you’re looking for, Rainy Day parts the clouds.

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

From charms to traditional wampum, CB Stark Jewelers’ timeless designs have been a hallmark of Island life for fifty years. Mark your Vineyard memories with a new charm every summer. Claudia presents a dazzling variety of designs from local and big-name international designers, plus high-end accessories and perfumes.

Best Men’s Clothing: Green Room

71 Main Street, Vineyard Haven, 508-693-6888, vineyardsurf.com

Runner-up: Sundog

41 Main Street, Edgartown, 508-627-5254

Plaid button-downs, Patagonia fleeces, Quiksilver board shorts, and everything in between is what you’ll find at the Green Room in winter, spring, fall, or summer. Sundog in Edgartown also has great finds, including tailored basics for a night out on the town and outdoorsy brands for a hike up-Island.

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

Service at the counter is prompt and personable, but that’s not the only reason Leslie’s Drug Store is the Best of the Vineyard winner. The aisles are stocked with school supplies, magazines, adhesive tape, and a fantastic nail polish selection. Conroy Apothecary’s staff is friendly and professional, and each location has a great selection of natural bath products in addition to first aid and medical supplies.

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

Frye, Mia, Hunter, Clarks, Toms, and Dansko aren’t members of a rock band. They’re shoes sold at the Green Room, and trust us, this selection of steppers is off the charts. Basics also keeps a well-stocked lot, with labels like Uggs, Sketchers, Adidas, and Frye.

Best Women’s Clothing: Green Room

71 Main Street, Vineyard Haven, 508-693-6888, vineyardsurf.com

Runner-up (tie): Basics Clothing Company

24 Circuit Avenue, Oak Bluffs, 508-693-8819, basicsclothingcompany.com

Slate

11 North Summer Street, Edgartown, 508-939-1908, slatemv.com

If you’re on a denim hunt, book it to the Green Room – you’ll find Sevens, Levis, Citizens, and True Religions aplenty. While you’re there, try on some North Face gear and browse the wide selection of leather goods. Slate in Edgartown guarantees one-of-a-kind fashion, including loop scarves made on-Island. Over in Oak Bluffs, Basics sells maxi dresses, casual T-shirts, sweaters, and accessories – proof that you don’t need to go off-Island to score a killer outfit.

Best Art Gallery: The 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

Whether you are a buyer or a browser, the Granary Gallery has enough art to satisfy a collector or looky-loo. Wander the field to look at sculptures, or head inside the red barn to see the diverse works on display. At the Eisenhauer Gallery, painters, jewelers, and sculptors can find space.