Chesapeake City, Maryland. Image credit: WhisperToMe, via Wikimedia Commons.

8 of the Most Overlooked Towns in Maryland

Maryland, the United States’ 9th smallest and 18th most populous state in the Mid-Atlantic region with stunning long coastlines along the Chesapeake Bay and the mighty Atlantic, is bounded by the District of Columbia in addition to the adjacent states of Virginia, Delaware, West Virginia, and Pennsylvania. Nevertheless, the state’s diminutive size belies its variety of climates and diverse topography ranging from the low-lying Eastern Shore to the forested Appalachian foothills in the West, which have helped Maryland earn the moniker “America in Miniature.” While thousands of travelers from all over the globe flock to the state’s crowded metropolises, such as Baltimore, Germantown, Annapolis, etc., all year round, the countless small towns in the state, too, need a similar kind of attention from vacationers. So, the next time you are on a vacation to the Old Line State, spare some time to tour these overlooked small towns.

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

Saint Michaels (also, St. Michaels), rightly called “The Heart & Soul of the Chesapeake Bay,” is a quaint harbor town along the 12.9-mile-long Miles River in Talbot County on Maryland’s Eastern Shore. Situated within an hour and a half drive from Washington, D.C., the town retains the look of a 19th-century seaport and proudly upholds its nickname “the town that fooled the British.” The walkable downtown is packed with numerous Victorian-era properties currently housing one-of-a-kind shops, boutiques, and outstanding bed & breakfasts. The Saint Michaels Mill, St. Michael’s Museum, Classic Motor Museum, Chesapeake Bay Maritime Museum, 1879 Hooper Strait Lighthouse, and a variety of art galleries like Gregorio Gallery, A.M. Gravely Gallery, Simply Dragonfly, Ouvert Gallery, and Hopkins Original Art are some of Saint Michaels’ prominent sites of interest. Taste the delicious cuisines served at the town’s exceptional restaurants like The Crab Claw, Ava’s Pizzeria & Wine Bar, Limoncello Italian Restaurant & Wine Bar, Bistro St. Michaels, and Justine’s Ice Cream Parlor.


Corner of Main and Water in downtown Thurmont
Corner of Main and Water in downtown Thurmont, By Andrew Bain - Own work, CC BY-SA 3.0,File:Thurmont MD Corner of Main and Water.jpg - Wikimedia Commons

This tiny Frederick County town, home to 6,935 inhabitants as per the latest US Census, is situated at the base of Catoctin Mountain, the Blue Ridge Mountains’ easternmost mountain ridge, along U.S. Route 15, roughly 10 miles from the state boundary with Pennsylvania. Thurmont is a favored destination for adventure lovers due to its closeness to the Catoctin Mountain Park with its scenic hiking and camping areas besides the Presidential retreat “Camp David,” and the Cunningham Falls State Park which has the state’s highest cascading waterfall and a 43-acre artificial lake that offers diverse water-based recreations. Additionally, Thurmont has several attractions including historic covered bridges, a walkable Main Street, the Thurmont Trolley Trail, the Catoctin Mountain Orchard, the Catoctin Breeze Vineyard, and the Catoctin Wildlife Preserve & Zoo. Every year, during the second weekend of October, the town hosts the Catoctin Colorfest, considered one of the East Coast’s biggest outdoor arts & crafts festivals that draws over 125,000 people.

Havre de Grace

Aerial view of Havre de Grace, Maryland, in autumn.
Aerial view of Havre de Grace, Maryland, in autumn. Image credit Wirestock Creators via Shutterstock.

Havre de Grace, named after Le Havre, a major French port city, is a serene Harford County hamlet at the head of the Chesapeake Bay and the Susquehanna River’s mouth, around 40 miles northeast of Baltimore. The town’s strategic location has made it the most coveted recreation and tourism destination especially renowned for its astounding bayfront views, elegant properties in the National Register-listed Havre de Grace Historic District, marinas, the restored Havre de Grace Promenade & Boardwalk, and captivating museums like the Havre de Grace Maritime Museum, Lock House Museum, Concord Point Lighthouse, and Decoy Museum. Havre de Grace’s two state parks: the Millard Tydings Memorial Park and the Susquehanna State Park are perfect for family-friendly activities like picnicking, camping, bird watching, hiking, fishing, boating, and horseback riding amidst spectacular surroundings.

Mount Airy

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

Mount Airy, placed on the border between Carroll and Frederick counties, forms a part of both the Baltimore-Columbia-Towson Metropolitan Statistical Area and the Washington Metropolitan Area. First settled in 1830 along the Baltimore & Ohio Railroad line, the town’s formal name was suggested by an Irish B&O worker, who while working on a windy day complained about his freezing ears due to the cool winds that blew across the railroad station at Parr’s Ridge. Mount Airy’s Main Street is lined by several buildings dating back to the late 19th or early 20th centuries, besides a plethora of boutique shops, parks, cafes, diners, galleries, farms like Knill’s Farm Market, Gaver’s Farm, and locally-owned wineries and breweries such as the Elk Run Vineyards, Black Ankle Vineyards, the Stillpoint Farm’s Milkhouse Brewery, and Linganore Winecellars.


The historic district of Berlin, Maryland.
The historic district of Berlin, Maryland.

A portion of the Salisbury, MD-DE Metropolitan Statistical Area, this small Worcester County town promoted as “America’s Coolest Small Town,” is situated approximately 10 miles inland from the Assateague Island National Seashore and Ocean City. Named after the vintage tavern “Burley Inn,” Berlin is widely known for its historic downtown commercial district and conjoining residential areas that comprise dozens of carefully preserved late-19th-century structures in various architectural styles lining the streets. Heritage buffs must not miss the Atlantic Hotel, Henry’s Grove, Merry Sherwood Plantation House, Burley Manor, Mermaid Museum, Rackliffe House, and the Calvin B. Taylor House Museum. The idyllic landscape of the state’s only oceanfront park - the Assateague State Park captivates the hearts of several nature enthusiasts. Downtown Berlin is chock-a-full of quirky shops, art galleries, and award-winning eating and drinking joints like Blacksmith, Burley Oak Brewing Company, The Globe, and Rayne’s Reef Soda Fountain & Grill. Annually, Berlin hosts a variety of events such as the Berlin Spring Cruisers Classic Car Show, Oktoberfest, 2nd Friday Art Stroll, Berlin Bathtub Races, Berlin Farmers Market, and Berlin Christmas Parade.

Chesapeake City

Overlooking Chesapeake City, Maryland.
Overlooking Chesapeake City, Maryland.

Originally dubbed the “Village of Bohemia” by Augustine Herman, a Bohemian explorer, this teeny town in northeastern Maryland’s Cecil County was renamed in 1839 after the Chesapeake & Delaware Canal (C &D Canal). Split into northern and southern segments following the construction of the canal, Chesapeake City is the state’s sole community to be situated along a working commercial canal. A majority of the town’s meticulously maintained 19th-century architecture is found on the southern banks of the canal, and several of these restored properties at present house art galleries, retail shops, entertainment venues, antique stores, boutiques, bed & breakfasts, and restaurants like Bayard House Restaurant. The C & D Canal Museum and Chesapeake Inn Restaurant & Marina are Chesapeake City’s other interesting sites. The principally residential northern portion of the town is esteemed for Schaefer’s Restaurant & Canal Bar and the 17-mile-long Ben Cardin C & D Canal Recreational Trail that links Chesapeake City with Delaware City.


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

Established in 1785 and christened in honor of a native landowner William Emmit, this picturesque town in northern Maryland’s Frederick County is situated about 0.3 miles south of the Mason-Dixon Line. Emmitsburg houses the principal campus of Mount St. Mary’s University (“The Mount”) - the country’s second-oldest Catholic university, in addition to other noteworthy places of interest like the National Shrine Grotto of Lourdes, the National Shrine of Saint Elizabeth Ann Seton, Emmitsburg Antique Mall, Frederick County Fire & Rescue Museum, and the National Fallen Firefighters Memorial. Moreover, the town is well-known for its thriving culinary scene, where an array of top-tier restaurants like the Carriage House Inn Restaurant, Ott House Pub, Rube’s Crab Shack, Chubby’s Barbeque, Carleo Italian Pizza, etc., serve everything from seafood, Southern-style cuisines, and Italian foods, to mouthwatering crab dishes.

North Beach

Waterfront houses and a boardwalk in North Beach, Maryland.
Waterfront houses and a boardwalk in North Beach, Maryland.

North Beach, a tranquil town occupying the northern tip of Calvert County on the western shores of the Chesapeake Bay, is an ideal beachside destination far away from the maddening crowds of Cambridge and Ocean City. Vacationers must take a stroll along the North Beach Boardwalk and witness unparalleled views of the Chesapeake, besides partaking in fishing activities at the public fishing pier and soaking in the town’s laid-back ambiance. Placed within walking distance from the pier are scores of shops selling antiques, gifts, and fine arts, aside from the cozy bakeries and excellent eateries that offer fine dining. The Bayside History Museum with its vast memorabilia collection gives a glimpse into the town’s glorious past, while nature lovers get to observe seasonal migrants and wetland wildlife in the tidal marshlands of the Wetlands Overlook Park.

From Saint Michaels - “The Heart & Soul of the Chesapeake Bay,” to Berlin - “America’s Coolest Small Town,” the small towns in Maryland entices holidayers with their distinctive charms. Boasting splendid coastal views, fascinating colonial architecture, lively cultures, fantastic cuisines, and a welcoming atmosphere, each of these lesser-known communities perfectly showcases the true heart and soul of the Free State. Whether you are visiting Maryland on a long vacation or a weekend trip, these overlooked towns promise unforgettable experiences for every visitor.

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