Top Shopping on Maryland’s Main Streets

When you shop along Maryland’s Main Streets, you’re supporting local businesses and the historic properties they steward. If window shopping by foot, dining at new spots, antiquing and collecting art sounds like a great day out, you’ll absolutely adore these Main Street destinations.

Shop the Shore in Berlin’s Unique Stores

With a population of about 4,900, Berlin is small but packs a lot of charm. This Eastern Shore gem, known for its great jewelry, gift and antiques shops, has both a Main Street and an Arts and Entertainment District. Year-round events include lawn concerts, pageants, Second Friday street festivals and quirky events such as bathtub races.

Fido-Friendly Shops in Frederick

Best known for its array of antiques, Frederick’s delightful downtown and Main Street offer an assortment of shops selling clothing, home furnishings, toys and more. A dog park and numerous pooch-friendly places make Frederick a great option for people traveling with pets. Make sure your trip coincides with one of the special events on the first Saturday of each month.

Crafters Heaven in Havre de Grace

In Havre de Grace, St. John Street anchors the shopping hub along the Susquehanna River. You will find shops specializing in everything from toys and candy to leather goods and global fair-trade crafts. From April through December, downtown streets close to traffic for festive First Friday block parties featuring live music and merchant promotions.

Rediscover Cumberland - The Queen City

Rediscover Cumberland, where history and modern charm converge. Explore the revitalized downtown with boutique shops, art galleries, and cafes. Nestled in the Appalachian Mountains, it’s a hub for recreation with access to the C&O Canal Towpath, Great Allegheny Passage, and Western Maryland Scenic Railroad. Enjoy scenic trails, rich architecture, and a perfect blend of adventure and culture.

Unique Shopping in Baltimore

Even in a big city like Baltimore, you'll find charming places to shop. Hampden, a neighborhood in Baltimore,  features unique second-hand shops and local artisan offerings. Baltimore County boasts Dundalk Town Center, one of the earliest shopping hubs in Maryland, dating to the early 20th century.

Old Meets New in Ellicott City

Long known for its antique shops, you’ll also find trendy boutiques and local artisans along Ellicott City’s historic Main Street. Take a break from shopping and relax in one of their specialty restaurants, which include fine French and global fusion spots and a brew pub. Events attracting visitors year-round include a plein air painting competition, farmers market, outdoor movie nights, ghost tours, concerts and festivals.

Eclectic Crisfield

This Eastern Shore small town is big on personality. cramped up its Arts and Entertainment District shopping opportunities thanks to a thriving community of visual and performing artists, writers and imaginative craftspeople. The Smith Island Baking Co. is among the many local businesses offering unexpected delights—like the official dessert of Maryland. The 10-layer Smith Island Cake features yellow cake and layers of chocolate icing. Crisfield also features a collection of both fun and fine dining.

More Maryland Main Streets

Historic Westminster’s cute downtown is lined with shops selling comics, ceramics, cycling gear, fashion jewelry and more. In Annapolis, shoppers enjoy a variety of upscale boutiques along picturesque Maryland Avenue, and Takoma Park reveals the town’s hippie heritage with merchants specializing in bicycles, beads and fair-trade artisan crafts at vintage-style boutiques. Find out more about Maryland's 34 Main Streets.