Holiday Shoppes & London Row

STROLL into CHESTERTOWN’S  SHOPPES, open 10 am – 5 pm
VISIT LONDON ROW on High Street, 11 am – 4 pm

Our shops and boutiques are chock full of wonderful finds for holiday giving: Gourmet foods, fine art, jewelry, crafts, apparel, home decor, toys and more. Bah Humbug to malls, and Amazon, too! Stroll around town and enjoy Chestertown’s unique history and charming architecture. We’ve been here since 1706!

Looking for a specific item or shoppe downtown? Here is our Downtown Directory. 

New this year: LONDON ROW, open 11 am – 4 pm
200 block of High Street

In addition to our wonderful shops, plan to visit London Row to find gifts with Victorian flair! Unique handcrafted items; visit the Millinery Shoppe for bonnets, top hats, bowler hats, muffs and newsboy caps. You’ll also love handmade candles, pottery, wood carvings, ornaments, textiles, chocolates, toffee, wreaths and fun Dickens items! So much to enjoy!

Here are just some of the vendors that will be on filling London Row with wonderful treats and treasures:

All Things UK
Chester River Soaperie
River Crafts
White Rose Herbals
McAllen’s Toffees
Galena Blooms Farm
Robbi & Matthew
Radcliffe’s Little Creek School (wreaths)
Angela’s Cottage
Sunny Fields Farm
Spa Angels
Main Street Millinery


There are just a few vendor spots open. Please review the registration requirements and submit an application if you would like to participate.