8 Prettiest Downtown Strips In Maryland

From the Chesapeake Bay to the Alleghenies, Maryland packs an unusually wide range of downtowns into a small state. Havre de Grace puts a half-mile boardwalk between its downtown and the exact point where the Chesapeake Bay and the Susquehanna River meet. Ellicott City stacks stone and brick shops up the hillside above the Patapsco. Annapolis builds its downtown around the oldest state capitol in continuous legislative use in the country. Here are eight of the prettiest downtown strips in the state.

Ellicott City

Downtown Ellicott City is the most photographed historic main street in the state. Stone and brick buildings climb the hillside above the Patapsco River, packed so tightly that shops, restaurants, and galleries line a street barely wide enough for two-way traffic. The B&O Railroad Station Museum anchors the lower end of Main Street and is the oldest surviving railroad terminus in America, built in 1830 as the western end of the first 13 miles of commercial rail in the country. The Thomas Isaac Log Cabin, from about 1780, and the Patapsco Female Institute ruins are other downtown stops.

The town has rebuilt twice since severe floods in 2016 and 2018 tore through Main Street. The result is a downtown shopped and dined in by people who care about keeping it here. Local institutions include Tersiguel's French Country Restaurant, the Ellicott Mills Brewing Company, and a rotating cast of antique stores and bookshops. Patapsco Valley State Park, minutes from downtown, has hiking, swinging-bridge access, and trails along the river that give the town its backdrop.

Havre De Grace

This charming waterfront lies at the confluence of the Susquehanna River and the Chesapeake Bay, forming the backdrop for a lively downtown strip. The wooden boardwalk along the Havre de Grace Promenade runs for roughly half a mile and is the ideal vantage point for travelers who want to take in the town's scenery on a morning or evening stroll. The 36-foot Concord Point Lighthouse sits downtown right along the river and is a favorite subject for photographers. It was constructed in 1827 and is one of the oldest lighthouses in Maryland.

There is much more to learn about the local fishing, crabbing, and sailing industries at the Havre de Grace Maritime Museum. The facility chronicles local maritime trade using preserved relics while further highlighting Native Americans and the Underground Railroad period. Meanwhile, antique collectors can find treasures from more than 50 dealers at Seneca Cannery Antiques and use the opportunity to check out paintings, beads, toys, carpets, furniture, decoys, and more.

Frederick

Frederick's downtown historic district covers roughly 50 blocks of 18th- and 19th-century architecture, making it one of the largest and densest in the state. The heart of the district is Carroll Creek Linear Park, a 1.3-mile stretch along a restored canal channel with a series of painted bridge murals, the most famous of which is William Cochran's trompe-l'œil "community bridge." Market Street is the main commercial strip, packed with restaurants, independent bookstores, and boutiques.

For local history, the National Museum of Civil War Medicine is in a restored downtown building and covers the field hospitals that treated wounded soldiers during the Antietam and Gettysburg campaigns. The Schifferstadt Architectural Museum, built in 1756, is the oldest standing house in Frederick and an important example of German-American vernacular architecture. The Weinberg Center for the Arts, a 1926 movie house on Patrick Street, hosts live music, theater, and film year-round, and Monocacy National Battlefield, just south of downtown, preserves the site of the 1864 Civil War battle that saved Washington, D.C.

Chestertown

History and the arts thrive along the quaint streets of this colonial town on the Eastern Shore. The downtown area hosts a spirited cultural scene, with a community of regional performers entertaining residents with theatrical performances at the Garfield Center for the Arts. On Saturday mornings, folks converge at the Chestertown Farmers Market to sell and buy a colorful array of products. Vendors spread out their flowers, meats, cheeses, handicrafts, and antiques as buyers look for something to spend their money on. Thanks to an energetic atmosphere, the market offers a great opportunity for socialization, with live music to set the mood.

Downtown Chestertown comes alive during many annual festivals, particularly the Chestertown Tea Party Festival. Parades, performances, and reenactments dominate the streets as families pay homage to a longstanding local tradition. At the Chestertown waterfront, newcomers can admire fascinating views of the Chester River or book a trip with the Chester River Packet Company for a cruise on the winding waterway inside a classic 65-foot yacht.

Berlin

Berlin hosts one of the prettiest downtown strips in Maryland, thanks to a busy Main Street Historic District lined with red-brick Victorian buildings. The Calvin B. Taylor House recreates 1800s life inside a restored Federal-style structure, with antiques, furniture, and other memorabilia from past eras on display. Main Street stays active year-round on the strength of the town's events calendar. Among these, the Berlin Fiddler Convention is well attended and brings music lovers together for two days of concerts. The event also celebrates local arts, crafts, and food.

Outside the festivals, downtown Berlin maintains its spark with over 60 boutiques, museums, galleries, retail shops, and other businesses, ensuring a sustained flow of activities. The Ghost Museum is an intriguing stop for paranormal fans, and its eccentric collection of relics, artifacts, and stories explores ghost sightings, paranormal encounters, and beliefs regarding the afterlife. Finally, those who fancy tasting the local nightlife can pop by Burley Oak Brewing Company for delicious root beer in a rustic venue with popular theme nights.

St. Michaels

A popular summer destination on the Chesapeake Bay, St. Michaels' vivacious downtown strip contains a mix of eateries, shops, galleries, and B&Bs. Walking down the busy Talbot Street exposes travelers to fine experiences, including a lesson about local history inside the Chesapeake Bay Maritime Museum. Located on a beautiful waterfront, the 1-acre campus exhibits world-class Chesapeake Bay artifacts, vessels, wrecks, and other memorabilia. The local seafood scene is a must-have for newcomers, who can head to the Crab Crawl for mouthwatering steamed crabs, crab cakes, and other staples of the Chesapeake cuisine.

Later, a wine-tasting tour at the St. Michaels Winery excites connoisseurs with over a dozen different varieties of fine local wines. Finally, don't leave without getting on the sparkling waters that surround St. Michaels. With Patriot Cruises, passengers enjoy a 70-minute sail on a luxurious double-decker boat, featuring narrations about the region's history and sightings of centuries-old mansions along the coast.

Cumberland

Cumberland is a pleasant Western Maryland community flanked by the Allegheny Mountains, whose historic downtown lies along the northern bank of the Potomac River. Several old buildings line its pedestrian-friendly streets, including the Second Empire-style Gordon-Roberts House. This restored 19th-century home of a local attorney exhibits Victorian furniture and other artifacts depicting life during the period. Cumberland's rich heritage is solidified by George Washington's Headquarters. The site features a dilapidated log cabin that twice sheltered America's first president as a military command post in the 18th century.

Vacationers who enjoy wine tastings are welcome to visit Charis Winery & Distillery, which handcrafts grape wines, fruit wines, and spirits in a premier downtown venue. Also, they can experience the beauty of Cumberland's outback aboard the Western Maryland Scenic Railroad, whose themed train excursions through the mountains deliver exciting sightseeing and photography opportunities.

Annapolis

The old meets the new in Maryland's charismatic capital, where a collection of 18th-century brick buildings cluster around a vibrant historic district. Famous among them all is the 1770s Maryland State House, the oldest state capitol building in the United States in continuous legislative use. Guests can take a 75-minute tour to glimpse its architectural heritage, explore the country's history, and learn about famous public figures who walked down its quiet hallways. Tourists also love convening at the Annapolis Harbour Center for some retail therapy. This popular lifestyle center houses numerous specialty stores, an Amish market, restaurants, and a movie theater for the public's entertainment pleasure.

Another vibrant spot in downtown is the Annapolis City Dock, filled with restaurants and bars, and hosts an array of popular events. Besides learning about the neighborhood's history over the past 400 years, tourists can explore the sprawling waters of the Chesapeake with a tour from Schooner Woodwind Sailing Cruises.

Walking Maryland's Main Streets

The prettiest downtown strips in Maryland can fill a weekend itinerary on their own. Walkable streets, proximity of attractions, and a steady rhythm of local events make it easy to move from one point of interest to another. Whether you want seafood on the waterfront in St. Michaels or the history of the State House in Annapolis, these are the downtowns worth starting with.