View of people enjoying a meal in one of the many local businesses in Annapolis, Maryland. Editorial credit: grandbrothers /

9 Towns in Maryland With Thriving Local Businesses

Maryland is a Mid-Atlantic state known for its vast coastline and cascading waterways. Along with natural beauty, it is the locally-owned cafes, boutiques, and markets that give Maryland its distinct flavor and appeal. Here, towns are not just buzzing locales but vibrant hubs of thriving local businesses that add depth and character to the state's cultural landscape.

Be it the capital city, Annapolis, or the coastal front town of Crisfield, these businesses are more than just places to shop and dine—they embody community spirit and entrepreneurial zeal. They provide a platform for local artists to showcase their talents, for farmers to sell their fresh produce, and for residents and visitors alike to connect over shared experiences and flavors.


Rustic brick buildings in downtown Berlin, Maryland.
Rustic brick buildings in the downtown area of Berlin, Maryland. Editorial credit: Kosoff /

Berlin charms visitors with its lovely downtown, earning it the title of “America’s Coolest Small Town.” Start your day at Blacksmith, a hip tavern with an eclectic menu featuring craft beverage options and farm-to-table dishes. Continue your journey with a visit to The Greyhound, a bookstore and fine arts gallery home to two rescued greyhounds, Penelope and Oliver, that visitors adore. Further along, kids are sure to love Rayne's Reef Soda Fountain & Grill, a historic diner from 1901 featuring great milkshakes and a soda fountain. Those looking for a full experience seek to explore The Globe—a restaurant and live music venue housed in a historic theater, for an all-in-one experience.


Aerial view of Sykesville in Maryland.
Aerial view of downtown Sykesville in Maryland.

Sykesville boasts a charming main street brimming with local businesses that embody the town's warm spirit. Upon arrival, visitors are drawn to French Twist Café, which serves authentic French pastries and crepes, perfect for breakfast. Local food markets like the Downtown Sykesville Farmers Market provide fresh produce and handcrafted goods, supporting the town's vibrant agricultural community.

Simultaneously, The Vine on Main is a delightful shop offering local wines, gourmet foods, and a live music series. Tourists can attend one of the many events here, such as Nathan Rowe in July or the Liberty Road performance in August. Revive & Company is another interesting pop-in with an array of upcycled furniture and home decor, blending vintage charm with modern style.


View of historic buildings in Cumberland, Maryland.
View of historic buildings in Cumberland, Maryland. Editorial credit: Kosoff /

Cumberland, the county seat of Allegany County, is a lively town with a local business scene that complements its setting in the Appalachian Mountains. While hiking and sightseeing are popular, there are plenty of great places in town to recharge one’s batteries. Dig Deep Brewing Co. is a local favorite, featuring craft beers brewed on-site and a welcoming atmosphere. Those not interested in drinking can opt for Queen City Creamery Scoop Shop, the place for award-winning frozen custard, ice cream, and even breakfast.

For a shopping spree, head to Barkin' Basement Thrift Shop, which sells secondhand treasures, or the Fort Cumberland Emporium, which sells antiques, local art, and collectibles. Both spots have plenty of unique items for the perfect souvenir. Furthermore, the Canal Place Farmer's Market is a local staple, providing fresh produce, baked goods, and artisan products.


An Ice cream shop along the harbor in Crisfield, Maryland.
An Ice cream shop along the harbor in Crisfield, Maryland.

Crisfield, aka the "Crab Capital of the World," has more than just seafood for tourists. Local artisans and crafters thrive in Crisfield, with shops like The Bay Gift Vault offering an array of unique gifts, handmade jewelry, and coastal decor. You should also add The Crisfield Artisan & Farmers Market to your list, where you will find fresh produce, baked goods, and handmade crafts every Saturday.

That said, those here for the famed seafood should head straight to Fisherman's Grille. This restaurant provides a fulfilling dining experience with local crabs and steak dishes highlighting the town’s maritime heritage. Alternatively, Gordon’s Confectionery, a historic spot since 1924, serves delicious homemade treats and light meals.


Businesses lined along the main street in Annapolis, Maryland
Businesses lined along the busy main street in Annapolis, Maryland. Editorial credit: Wirestock Creators /

Maryland's Capital, Annapolis, is a bustling hub of 40,000 residents, always full of vibrance. Along with its coastal charm, vast heritage, and cultural appeal, this town is full of thriving local businesses. 49 West Coffeehouse, Winebar & Gallery is where visitors can enjoy a hearty breakfast, great coffee, and live music in a lively atmosphere. Nearby, Bean Rush Café is another popular store offering organic coffee and delicious pastries.

Art lovers will find a treasure trove in Annapolis, with shops like Gallery 57 West showcasing works from local artists, including paintings, photography, and handcrafted jewelry. Similarly, the Annapolis Pottery displays beautiful, functional pottery made on-site, perfect for gifts or home decor. Finally, the Pennsylvania Dutch Farmers Market is known for fresh meats, baked goods, and handmade crafts, providing a taste of Amish country in Annapolis.


Buildings in Westminster, Maryland.
Shops and stores along the main street of Westminster, Maryland. By Farragutful - Own work, CC BY-SA 4.0, Wikimedia Commons.

Just under two hours from Washington, D.C., you will land in the historically significant town of Westminster. After visiting landmarks such as the famed Hadhawha Tower windmill, it's time to check out the town’s booming local businesses. One popular spot is JeannieBird Baking Company, which promises a lip-smacking menu of pastries, cakes, and sandwiches made from scratch. For a hearty meal, visit Rafael's Steak & Oyster, a good option for classic American fare.

For fresh produce and local specialties, Carroll County Farmers Market is a must-visit. It features seasonal fruits, vegetables, baked goods, and crafts from local vendors. Alternatively, Baugher’s Orchard & Farm Market offers opportunities like pick-your-own strawberries along with fresh fruits, vegetables, and homemade products, making it a favorite among locals.


Main Street in Frostburg, Maryland.
Main Street in Frostburg, Maryland. By Famartin - Own work, CC BY-SA 4.0, Wikimeda Commons.

Another Allegheny Mountain town, Frostburg, supports a vibrant community fueled by local businesses and a rich cultural scene. Art enthusiasts should explore the Mountain City Traditional Arts shop, displaying local crafts, music, and art. Similarly, Frostburg Fiber Depot takes pride in its selection of yarns and fibers, which are perfect for knitting and crochet enthusiasts. Main Street Books is an independent bookstore with a carefully curated collection of books and a cozy reading nook since 1989.

After roaming around, visitors can check out Princess Restaurant, a local institution known for its nostalgic 1950s diner vibe and delicious comfort food. Meanwhile, those with a sweet tooth can head to Mountain City Coffeehouse & Creamery for homemade ice cream and freshly baked goods.

Takoma Park

Businesses in downtown Takoma Park, Maryland.
Businesses in the downtown area of Takoma Park, Maryland. By Farragutful - Own work, CC BY-SA 3.0, Wikimedia Commons.

Takoma Park, in the news for its progressive community and eclectic vibe, is a haven for local businesses and cultural diversity. Busboys and Poets is a local café doubling as a bookstore and community hub, offering great coffee, delicious food, and frequent cultural events. You can also relish wood-fired pizzas made with fresh, local ingredients at Roscoe’s Pizzeria.

Art and culture are at the heart of Takoma Park, with shops like Sankofa Video Books & Café providing books, music, and cultural artifacts. Tabletop is another charming boutique featuring an array of home decor, gifts, and local art. The town’s highlights include the Takoma Park Street Festival, an annual event celebrating local artists, musicians, and vendors.

Havre de Grace

A vibrant ice cream bench in Havre de Grace, Maryland.
A vibrant ice cream bench in Havre de Grace, Maryland. Editorial credit: George Sheldon /

Havre de Grace, one of the most prominent Maryland towns on the Susquehanna River, also shines for its local establishments. Java by the Bay, an unassuming café serving gourmet coffee and tasty pastries, makes for a good start. Afterward, oenophiles can head to The Vineyard Wine Bar, a chic attraction with a selection of fine and vintage wines and gourmet tapas.

Similar to most Maryland towns, art and culture thrive in Havre de Grace. Arts by the Bay Gallery showcases works from local artists, including paintings, sculptures, and jewelry, making it a great spot to find unique pieces. Joseph's Department Store, a historic shop that has been serving the community since 1937 and provides a range of quality clothing and accessories, is a definite stop when in town.

Wrapping Up

From the coastal delights of Crisfield to the historic charm of Havre de Grace, the towns in Maryland have stops like cafes, artisanal shops, and food markets that celebrate local talent and craftsmanship. These Maryland towns exemplify how local businesses can thrive and become the heart of their communities, offering unique products, personalized services, and a sense of connection that large chains simply cannot replicate. The commitment of these communities to support and celebrate their local businesses not only sustains their economies but also preserves the distinctive character of each town.

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