Aerial sunset panorama of Havre de Grace Maryland with orange sky and clouds reflecting on the Susquehanna River and the Chesapeake Bay

6 Darling Small Towns in Maryland

Maryland, one of the initial Thirteen Colonies and the 7th state to be officially admitted to the Union, is an eye-catching Mid-Atlantic state at the heart of the Eastern Seaboard. Nonetheless, the state’s small size credibly conceals its varied landscapes ranging from the low-elevation, hydrophilic Atlantic Shore and Chesapeake Bay area to the sylvan Appalachian foothills and highlands in the West, that have helped Maryland duly earn its sobriquet ‘America in Miniature.’ Even though, the population centers of the ‘Old Line State’ including the state capital Annapolis, the largest city - Baltimore, and other big cities like Columbia and Germantown are massive tourist drawers, the innumerable darling small towns often remain unnoticed. So, on your upcoming holiday trip to the ‘Free State,’ spare some time from your crazy schedules to discover everything these tiny communities have to offer.

Saint Michaels

Colorful shops on Talbot Street in Saint Michaels, Maryland
Colorful shops on Talbot Street in Saint Michaels, Maryland. Image credit blubird via Shutterstock

Rightly dubbed, “The Heart & Soul of the Chesapeake Bay,” this picturesque waterfront town is situated on Maryland’s Eastern Shore next to the Miles River in Talbot County. Placed only an hour and a half drive from Washington D.C., Saint Michaels carefully preserves its look of a 19th-century seaport boldly ratifying its moniker: ‘the town that fooled the British.’ Sightseers must explore the Chesapeake Bay Maritime Museum, Classic Motor Museum, A. M. Gravely Gallery, St. Michaels Museum, Saint Michaels Mill, and 1879 Hooper Strait Lighthouse. Also, peruse the umpteen trendy boutiques, quirky shops, first-class bed & breakfasts like The Old Brick Inn, and upscale restaurants like Limoncello Italian Restaurant & Wine Bar, and Carpenter Street Saloon in the town’s walkable downtown.

Bel Air

South main street in Bel Air, Maryland
South main street in Bel Air, Maryland. Image credit Yaoiloverr Yaoiloverr, CC BY-SA 4.0 via Wikimedia Commons

The seat of government of Harford County, this laid-back community is located precisely 30 miles north of downtown Baltimore in Northeast Maryland. Initially planned on a portion called ‘Scott’s Old Fields’ of Aquilla Scot’s inherited land, Bel Air and its adjoining suburbs have expanded rapidly over the years, changing the town into a principal governmental, medical, educational, cultural, and commercial magnet. While in Bel Air, take note of some outstanding sites of interest like the Bel Air Armory, Liriodendron Mansion, Tudor Hall, Harford Mall, etc., besides hiking by the Ma and Pa Trail. Encompassing a substantial part of the downtown, the Bel Air Arts and Entertainment District is especially used for concerts, festivals, theaters, art galleries, dance performances, and diverse annual celebrations. The town’s solitary community park - Rockfield Park and five other urban parks provide profuse leisure facilities such as recreation zones, picnic facilities, horticultural gardens, a comprehensive trail network, and an amphitheater supporting a vibrant summer concert series.

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 / Shutterstock.com

Havre de Grace, labeled after a significant port city in France, is an impeccable Harford County hamlet placed at the meeting of the vast Chesapeake Bay and the Susquehanna River, roughly 40 miles northeast of the state’s most populous city. An appealing recreation and tourism mecca, the town is famed for its incredible waterfront scenes, the Havre de Grace Historic District’s magnificent Victorian properties, the renovated Havre de Grace Promenade & Boardwalk, and engaging museums such as the Decoy Museum, Concord Point Lighthouse, Havre de Grace Maritime Museum, and Lockhouse Museum that tells stories about the town’s rich maritime heritage. Outdoorsy types get to partake in birdwatching, horseback riding, boating, picnicking, fishing, camping, and horseback riding activities amidst the impressive settings of the Millard Tydings Memorial Park and the Susquehanna State Park.

Thurmont

Downtown Thurmont, Maryland.
Downtown Thurmont, Maryland. Image credit Andrew Bain, CC BY-SA 3.0, Wikimedia Commons

Having 6,935 inhabitants, this teeny Frederick County community sits at the eastern base of the Blue Ridge Mountains’ Catoctin spur, alongside the U. S. Route 15 Highway, about 10 miles from the state boundary with Pennsylvania. Thurmont’s proximity to the Catoctin Mountain Park with its glistening streams, sweeping vistas of Monocacy Valley, and attractive hiking and camping areas have made it the most sought-after destination for thrill-seekers. The town is also close to the Presidential retreat - “Camp David” and the 6,080-acre Cunningham Falls State Park featuring the remnants of an ancient blast furnace, the Cunningham Falls - Maryland’s highest cascading waterfall, and a 43-acre artificial lake which provides opportunities for ample water-based recreations. Moreover, vacationers are also enticed by a large number of historic covered bridges, the Catoctin Wildlife Preserve & Zoo, Catoctin Mountain Orchard, Thurmont Trolley Trail, and Catoctin Breeze Vineyard. Annually every second weekend of October, thousands of revelers flock to the town to attend the Catoctin Colorfest - one of the largest outdoor arts and crafts festivals on the East Coast.

Mount Airy

Main street in Mount Airy, Maryland
Main street in Mount Airy, Maryland. Image credit: Acroterion via Wikimedia Commons.

Straddling the borderline betwixt Frederick and Carroll counties, Mount Airy forms a portion of both the Washington Metropolitan Area and the Baltimore-Columbia-Towson Metropolitan Statistical Area. Initially settled alongside the Baltimore & Ohio Railroad line in the early 1830s, the settlement’s ceremonial name was suggested by an Irish B&O employee who on a windy working day whined about his frostbitten ears due to the freezing winds that blew across the train station at Parr’s Ridge. When visiting the town, stroll down the inviting Main Street choke-full of countless historic properties, parks, boutiques, galleries, cafes, eateries like Concetta’s Main Street Bistro Restaurant and Mount Airy Inn, local farms like Knill’s Farm Market, independent wineries and breweries like Black Ankle Vineyards and Milkhouse Brewery at Stillpoint Farm.

Emmitsburg

A barn with silo on a farm near Emmitsburg, Maryland.
A barn with silo on a farm near Emmitsburg, Maryland.

Christened after the local landowner William Emmit, this adorable Frederick County community in Northern Maryland is situated around 0.3 miles south of the Mason-Dixon Line, close to the state boundary with Pennsylvania and 23 miles north-northeast of Frederick. Aside from housing the central 1,400-acre campus of Mount St. Mary’s University, Emmitsburg’s other notable sites of interest include the National Shrine Grotto of Lourdes, National Fallen Firefighters Memorial, Emmitsburg Antique Mall, National Shrine of Saint Elizabeth Ann Seton, and Frederick County Fire & Rescue Museum. Furthermore, gourmets get to savor finger-licking crab dishes, Southern-style cuisines, and Italian dishes served by the town’s world-class eateries like Carriage House Inn Restaurant, Carleo Italian Pizza, Ott House Pub, Chubby’s Barbeque, and Rube’s Crab Shack.

From the enchanting Havre de Grace to the picture-perfect Saint Michaels, the 9th smallest and 18th most populous state of the nation is dotted with a cornucopia of tiny settlements hypnotizing holidayers from all over the globe. Boasting extraordinary coastal vistas, riveting colonial past, booming community spirit, local eateries serving mouthwatering cuisines, and harmonious surroundings, these small communities typify the inner essence of ‘Little America.’ Whether you want to be amused by the outdoors, witness age-old architecture, and revel in high-street shopping, these homely towns are worth adding to your travel plans.

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