Where to Shop 

Aquinnah/Chilmark:
Up Island’s utilitarian and unique style is reflected in the merchandise found here.
Check Out: 
Menemsha Blues t’s
Pandora’s Box  for easy, beach to garden party clothing
For handcrafted wampum jewelry, Stony Creek and How-Wass-Wee gift shops at the Cliffs
  
Edgartown:
Shop here for hot brand names and preppy must haves.
Check Out:
Molly B’s selection of  7’s and  Kate Spade accessories.
Vineyard Vines’ understated signature Vineyard collection.
Island Pursuit and Sundog for a yachty look
The Boneyard for surfing gear
Dressing up? Head over to The Great Put-on

West Tisbury:
Arty and a bit homespun, achieve that unstudied Vineyard look in laid-back natural fiber clothing.
Check Out:
The Red Mannequin for something funky and fashionable
Bananas Gallery where clothing is just another art form

Oak Bluffs:
Shop for souvenirs, t’s, retro, silver jewelry and party wear.
Check Out:
Laughing Bear for romantic, 60’s-informed styles and accessories, Jamaican Jam-when it’s beach party time on the Island, Nautilus Gift Shop, a one stop shop for souvenir t's and more Third World Trading for hand-crafted clothing.                                    

Vineyard Haven: 
Shop January through December in this, the Island's year-round port of call.
Check Out:
The Green Room for Patagonia and North Face apparel
The ultimate in bohemian chic at Alley Cat
Rainy Day, Le Roux, Nochi and Mix for beautifying  your home 

When to Shop
<See what's on sale now!>

January/February: 
Though Christmas sales are over, shops that are still open feature sale racks with an ever-changing selection of merchandise.  If the weather’s fine, some shops that are closed will open for an odd weekend, offering rock bottom prices with an eye to clearing inventory before spring. 
Check out:  
The Green Room
Bryn Walker (VH store)

March/April: 
With folks starting to come up over the weekends, shops reopen to accommodate early season shoppers.  Sales racks bulge as retailers that are open all year clear out cold weather stock.  Seasonal merchants deeply discount last year’s inventory.
Check out:  
Katydid in Edgartown
Midnight Farm in Vineyard Haven

May/June/July/August:
Sales become scarce as the summer comes into its own.  Shop for your home, as seasonal decorative merchandise is marked down. 
Check out: 
Trader Fred at the Triangle in Edgartown and downtown VH for year round bargains. Frequent turnover.
Garden centers for markdown merchandise as the growing season progresses.

September/October:
You’ll find the biggest markdowns at shops that are closing for the season.  Columbus Day is a truly significant benchmark holiday for serious bargain hunters.
Check Out:
The Beach House in Vineyard Haven
Petunia’s Shoes and Saffron in Edgartown


November/December: Sale racks once again dot the landscape.  Year-round businesses and those that stay open through the holidays clear out  to make room for seasonal merchandise.  Shopping for stocking stuffers? Right around the holidays Katama General Store and Morning Glory Farm close up shop, providing great deals on a variety of local treats.
Check Out:
Rainy Day in Vineyard Haven
Saffron, Edgartown