Chestertown, Maryland, offers more than scenic waterfront views and rich history—it’s also a haven for unique shopping experiences. Whether you’re searching for artisan crafts, antiques, or the perfect gift, these shopping destinations make for the ideal weekend outing. Here are our top picks for places to shop and explore in Chestertown:
Chestertown Farmers’ Market
Where Local Meets Artisan
Start your weekend in the heart of Chestertown at the vibrant Farmers’ Market. Held every Saturday morning from 8AM to Noon, this market is a community favorite. You’ll find everything from fresh produce and baked goods to handmade crafts and local artwork. It’s the perfect spot to grab a coffee, browse, and soak up the town’s charming atmosphere.
What You’ll Find:
- Fresh produce and flowers
- Handcrafted jewelry and pottery
- Locally made jams, soaps, and more
Why We Love It:
The Farmers’ Market is more than just a place to shop—it’s a gathering spot that showcases the best of Kent County’s creative and culinary talent.
Twigs & Teacups
Boutique Charm in Downtown Chestertown
Twigs & Teacups is a beloved local boutique offering a carefully curated selection of gifts, home décor, and accessories. Whether you’re looking for a special gift or just indulging in a little retail therapy, this shop is a must-visit.
What You’ll Find:
- Unique home décor items
- Stylish clothing and accessories
- One-of-a-kind gifts
Why We Love It:
The warm, welcoming atmosphere and eclectic finds make Twigs & Teacups a favorite for locals and visitors alike.
Chester River Wine & Cheese Co.
A Gourmet Stop for Foodies
If your shopping plans include delicious treats, Chester River Wine & Cheese Co. is the place to go. Located in Chestertown, this specialty shop offers gourmet cheeses, wines, and other culinary delights that make great gifts—or indulgent snacks for yourself!
What You’ll Find:
- Artisan cheeses and charcuterie
- Fine wines from around the world
- Gourmet snacks and pantry items
Why We Love It:
It’s a foodie’s dream destination, perfect for picking up something special to enjoy during a weekend getaway.
Plan Your Shopping Weekend
Chestertown’s diverse shopping destinations provide a little something for everyone, whether you’re looking for unique gifts, local goods, or just a fun day of exploring. With charming boutiques, artisan markets, and gourmet stops, a weekend in Chestertown, MD is the perfect opportunity to shop and support local businesses.
What’s Your Favorite Spot?
Did we include your go-to shopping destination? Let us know your favorites in the comments below!
