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Top Shopping on Maryland’s Main Streets

By Jennifer Broadwater

Find must-have treasures in Maryland’s unique shopping districts.

shop in Annapolis
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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.

Rustic and Rootsy Cumberland

Set among the Allegheny Mountains, Cumberland’s railroad roots have given way to an arts focus in the town’s open-air pedestrian Town Centre. Shops include country décor, a tea parlor and studios specializing in woodwork, leather, pottery and yarn. Don’t miss the Western Maryland Scenic Railroad Gift Shop, which celebrates all things locomotive.

Unique Shopping in Baltimore

Even in a big city like Baltimore, you'll find charming places to shop. Hampden, a neighborhood in Baltimore, features 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 33 Main Streets.
Shopping in Frederick
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