The charming towns around Chesapeake Bay are beautiful, but they’re also full of small businesses that are important to the local way of life and the economy. These businesses, from family-run stores and restaurants to shops selling crafts made by local fishermen, make each town special. These towns are proud of their small businesses and love to welcome visitors to explore their lively main streets.
Explore the charming towns and support their small businesses! From Virginia to Maryland, these towns offer unique shops and local experiences that capture the spirit of the region. Take your time browsing and enjoy the friendly atmosphere.
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Chestertown, Maryland
Chestertown is a charming small town in Kent County that attracts tourists with its peaceful vibe. Visitors can enjoy exploring the quaint downtown area, which is full of family-owned shops. Despite being a small place, Chestertown surprises many shoppers with its variety of stores. At Bee Crafty Collectibles, you can find a unique mix of artsy items, like upcycled furniture, home decor, and custom-made signs, perfect for gifts or souvenirs. Another great spot is Maryland Shore Auctioneers, where you can discover antiques, jewelry, coins, and Amish goods.
Chestertown has a busy Farmers Market in the downtown area where you can buy fresh produce, local crafts, and other interesting items. There are plenty of places to eat in Chestertown. If you get hungry, you can try the food at Luisa’s Cucina Italiana or Jellyfish Joel’s Beach Bar.
St. Michaels
St. Michael’s charm comes from its relaxed coastal scenery and stunning views of the Chesapeake Bay. This small harbor town also has a quaint downtown with many friendly family-owned businesses. Art lovers will enjoy Creative Xpressions, which has unique picture frames, home accessories, and gift items at great prices. The St. Michaels Farmers Market is a great place to shop for fresh fruits, vegetables, seafood, flowers, baked goods, and locally-made alcohol.
Many visitors to St. Michaels love trying the famous Chesapeake Bay cuisine. The town has several family-friendly restaurants to satisfy every appetite, including The Fool’s Lantern and Ava’s Pizzeria & Wine Bar.
Rock Hall, Maryland
This small village in Kent County has a rich history that goes back over three hundred years. Located on the National Chesapeake Scenic Byway, it offers tourists amazing water views. Visiting the small businesses in downtown Rock Hall lets you experience the town’s unique atmosphere. The Bay Escape is a great place to shop for jewelry, houseware, purses, and more. Another good spot is Fresh Start Food and Garden, where you can find natural foods, local produce, meats, and cheeses in a charming open-air market.
The Hickory Stick impresses tourists with its wide range of items, including charms, gifts, beads, and houseware. After a successful shopping trip, visitors can head to the Blue Heron Oyster House Inn for a delicious seafood meal.
Cambridge, Maryland
This gem in Dorchester County has a lively downtown with a great mix of businesses. It’s a fantastic place for small-time shoppers, with various locally owned stores for all your needs. Urban Wear is a popular clothing store in downtown Cambridge, selling trendy T-shirts that make great Maryland souvenirs. Shorelife Home and Gifts is the ideal shop for beautiful home decor and gift items like glassware, rugs, lamps, artsy candles, and faux potted plants.
Those wanting fresh farm goods will love Emily’s Produce, which offers a variety of fruits and vegetables from local farmers. Cambridge is also a great place to try Maryland’s rich seafood heritage, with restaurants like Ocean Odyssey Crab House & Seafood Restaurant.
Onancock, Virginia
One of the most charming towns in Chesapeake Bay, this delightful spot is located in the Virginia part. With a small population of about 1,000 residents, the town has a strong small-business community, with locally-owned stores as the backbone of downtown. Visitors can enjoy shopping at the Onancok Farmers and Artisans Market, where vendors and buyers from the community create a lively social scene. Antique lovers can find unique treasures at Timothy Smith and Sons, which specializes in fine art, antique furniture, collectibles, and other souvenirs.
When it’s time to eat, the Corner Bakery offers delicious pastries and sandwiches in a charming downtown cafe, while Mallards at the Wharf serves full meals in a lovely waterfront setting.
Easton
In Maryland, Easton is known for its art scene and cultural centers. Visitors can find great souvenirs at places like Troika Gallery and Tripe Gallery. La De Da is a hit with female shoppers for its trendy fashion accessories like clothes and shoes. And if you’re new to Easton, you should definitely check out the Amish Country Farmers Market.
At the Amish Country Farmers Market, besides enjoying the cultural experience and friendly vendors, you can also try tasty homemade baked goods and buy special handmade crafts. If you’re into fancy dining, think about visiting Bas Rouge.
Cape Charles, Virginia
Cape Charles is a beautiful spot on the Atlantic Ocean coast, perfect for sightseeing and shopping. Despite its relaxed rural vibe, it has a lively town center with thriving local businesses. Seafood is a big part of the town’s culture, and places like The Shanty serve delicious fish, oysters, and shrimp. You can also find fresh produce at groceries like Gull Hummock Gourmet Market and Drizzles.
If you love fashion and want to do some shopping on your trip, check out Coastal Charm Boutique! This popular store has lots of trendy clothes and accessories – perfect for finding something new and stylish.