9 Of The Most Adorable Small Towns In Maryland
In Maryland, small-town charm comes with a few unexpected twists. One historic Civil War town has traded battlefield action for local wineries and model trains, while another, less than 40 miles from Baltimore, draws visitors with its farm-fresh produce and countryside appeal. Head west, and the Appalachian Mountains set the scene for cozy communities surrounded by forested trails and sweeping overlooks. Along the Chesapeake Bay, sailboats bob in picturesque harbors, while the Atlantic Coast offers a nostalgic beach escape complete with a historic boardwalk. Full of mountain retreats and waterfront communities, these nine adorable Maryland towns prove that personality often comes in small packages.
Westminster
Right in the heart of Central Maryland, about 38 miles northwest of Baltimore, Westminster is a fruitful town that's constantly growing some great goods. The Carroll County Farm Museum makes a nice starting point for exploring the region's agricultural heritage, complete with one of the state's best collections of historic farm machinery, a number of kid-friendly activities, and a calendar full of special events (such as arts-and-crafts classes and winter-holiday open houses). For even more farm-fresh goodness, folks can go to Baugher's farm and find some fresh produce at the orchard market and house-baked treats at the bakery. And for a more mature farm outing, adults can make a reservation to visit Old Westminster Winery, then discover an impressive lineup of terroir-driven, eco-friendly wines.
A short drive west of town leads to Sunday Morning at Savannah's, a curiously named place that features cozy, comfy homestyle accommodations, soothing in-house spa treatments, and their Sunday Morning Coffee Lounge, which is worth the drive in and of itself.
Friendsville
Friendsville may be the oldest European-colonist settlement in Garrett County, yet it's also a refreshing town by the Youghiogheny River, where one can find some much-needed rejuvenation. Right by the river, folks can take the Kendall Trail and follow the path of a late 19th-century railbed through a lush patch of forest. A little way north of town, Mill Run Recreation Area marks a beautiful space for hiking and biking near the Pennsylvania state line. And after a good time exploring the Appalachian countryside, visitors can return to town for a stop at The Root Cafe with a menu full of delicious farm-to-table fare.
For the friendliest stay in Friendsville, it's worth the drive out to Yorkie Acres Farm for a glamping farm stay. They have a full yurt set up alongside a bathhouse and a galley-style kitchen, and they have a full family of farm animals to greet you on the property.
Cumberland
Cumberland is a roughly 106-mile drive southeast of Pittsburgh (Pennsylvania), yet this Maryland town sets the scene for a serene Appalachian Mountain sojourn. From the center of town, it's easy to catch the Great Allegheny Passage and hike or bike along this 149-mile path that runs through plenty of gorgeous Appalachian wilderness all the way to Pittsburgh. It's also a short drive out to Rocky Gap State Park, a 3,000-acre preserve with a mile-long gorge, the 243-acre Lake Habeeb, often cherished for having "the bluest water in the state," and a variety of multi-use trails winding through the leafy hemlock forest. And for those wanting to explore a different side of Cumberland, the C. William Gilchrist Gallery and Museum occupies a stately 19th-century Federal-style mansion downtown and showcases an esteemed collection of local historical artifacts and nationally recognized visual art exhibits.
Staying downtown, The Wills Hotel is a charming 20-room boutique hotel with stylish accommodations and sweet amenities like plush bedding, HDTVs, mini-fridges, and premium bath products. In addition, they have the 1867 restaurant, serving a modern, elevated take on classic chophouse fare.
Sharpsburg
Near the site of one of the most notorious battles of the Civil War, Sharpsburg packs in a whole lot of American history, but this town also showcases a much more peaceful and pleasant present-day reality. A major draw here is Antietam National Battlefield, the site of the 1862 battle that was the bloodiest of the Civil War, ultimately marking a turning point in favor of the Union Army, and now protecting a calm expanse of countryside along Antietam Creek. Then, for a taste of what's happening now, folks can head over to Antietam Creek Vineyards and explore some local viticulture while enjoying some of their fine estate-grown wines. And at Antietam Station, visitors will find the Hagerstown Model Railroad Museum and its impressive model train setup.
Centrally located in town near the Antietam Battlefield, The Inn at Antietam is a warm and welcoming bed-and-breakfast featuring classically elegant rooms, free guest parking, on-site electric car charging, and a complimentary breakfast every morning.
Havre de Grace
Where the Susquehanna River meets Chesapeake Bay, roughly 65 miles southwest of Philadelphia (Pennsylvania), Havre de Grace really lives up to its name (as in, French for "harbor of grace") with beautiful waterfront scenery and unique cultural delights. Right by the waterfront, the Havre de Grace Decoy Museum has an extensive collection of duck decoys, helping to preserve a fascinating facet of local tradition. A few steps away, the Concord Point Lighthouse has been a beacon since 1827 and continues to offer an illuminating experience to visitors. And for those wanting to sail the open water, BaySail provides professional sailing courses and fine watercraft available for charter rental.
Vandiver Inn has a convenient downtown location, but this boutique hotel looks and feels like a bucolic country inn, with a lush garden outside and historically charming guest quarters and top-notch guest service inside.
Annapolis
It's not often that a state capital gets described as an adorable small town, but Annapolis is no ordinary state capital. In town, folks can check out the Banneker-Douglass-Tubman Museum and get a comprehensive view of African-American history and culture, including exhibits of works by local Black artists and displays of their thought-provoking archives and artifacts. A few blocks east, the Maryland State House is itself a stately 1779 historic landmark, and it's regularly open for visitors to walk inside this special structure that's witnessed everything from the ratification of the 1783 Treaty of Paris that formally ended the Revolutionary War, to debates on desegregation following the U.S. Supreme Court's 1954 Brown v. Board of Education decision. And a few miles north of downtown, Cantler's Riverside Inn is another impressive landmark for some classic Maryland seafood, including crab cakes and locally sourced rockfish.
Just across the street from the State House, 86 State Circle is a luxury boutique hotel that brings a new air of sophistication to old Annapolis. Inside an 18th-century historic townhouse lies a refined assortment of rooms and suites equipped with luxury memory foam mattresses, premium linens, HD smart TVs, individual climate control, and bathrooms with heated tile floors and full soaking tubs. While here, guests also enjoy exclusive access to the hotel's Black Pearl speakeasy lounge.
St. Michaels
Around 81 miles east of the hustle and bustle of Washington, D.C., there's much smoother sailing to be found in the nautically oriented town of St. Michaels. This comes into clear view at the Chesapeake Bay Maritime Museum, which includes the 1879 Hooper Strait Lighthouse, a fully operational shipyard, and even a floating fleet of boats that continue to sail the open waters of Chesapeake Bay. Or, for a more tranquil take on the local waterfront, folks can walk or bike along the St. Michaels Nature Trail. And for a delectable taste of the aquatic bounty, visitors can book a table at Talbot St. Tavern and feast on some fantastic Maryland seafood.
A short stroll or drive from the museum, the Inn at Perry Cabin takes up 26 acres of prime real estate by the Miles River, and it's the ideal luxury resort for anyone hoping to sail the bay on one of the resort's fine vessels. But even for guests who want to spend more time on dry land, they can relax in some very well-appointed accommodations, enjoy some distinguished Chesapeake cuisine at STARS Restaurant and Purser's Pub, and book a treatment at the SPA at Perry Cabin.
Scotland
Turning to the southern tip of the St. Mary's Peninsula, Scotland is a town where the good vibes flow freely at the junction of the Potomac River and Chesapeake Bay. To the north, St. Inigoes State Forest protects the United States' oldest known Jesuit establishment, and this hallowed ground makes for a very tranquil experience in open nature. Then, for a good launch point to great times on the water, Buzz's Marina offers top-notch facilities for sailors, campers, and fishermen alongside quick and easy bay access. And at the southernmost point of the peninsula, Point Lookout State Park has everything from a 710-foot fishing pier to ample beaches and campsites for a fun outing at the bayfront.
The Hideaway in Hays Beach sits a few steps from the beach in Scotland, and it's a vacation home with a fully equipped kitchen, three comfortably furnished bedrooms, a spacious open-plan living room, and even a covered back porch with a Kenmore Elite Gas Grill ready to use.
Ocean City
Perched on the Delmarva Peninsula's Atlantic Coast, and about 147 miles southeast of Baltimore, Ocean City really does function as Maryland's window to the sea. This becomes quite apparent at the famed Ocean City Boardwalk, a century-old historic landmark that continues to serve as a vibrant hub for shopping, dining, and entertainment at the seashore. But for anyone who prefers a quieter time in nature, it's a short drive out to Isle of Wight Nature Park, a beautiful island with a small beach, a fishing pier, and open picnic tables. Or, back in town, folks can head up to 71st Street Beach for a quieter stretch of sand at the foot of the Atlantic Ocean.
A few blocks north of Ocean City Expressway, Sunset Island is a convenient yet quiet 37-acre bayfront community offering serene and spacious condo-style vacation rentals alongside private beaches, boat slips, an on-site market, a fishing and crabbing pier, and even an indoor heated swimming pool that stays open year-round.
Find New Adorable Wonders Across the Old Line State
Maryland might be the ninth-smallest state by land area, yet it goes above and beyond to offer a wealth of adorable scenery and distinctive culture. Cumberland is an outdoor adventurers' paradise with a number of parks and trails leading to open Appalachian Mountain wilderness. Sharpsburg may be home to the historic Antietam Battlefield, yet it's also a town with good wines and cute model trains. Havre de Grace might be famous for its decoys, but there's nothing fake about its charming bayfront setting. Speaking of the Chesapeake Bay, the state capital, Annapolis, has an abundance of unique historic landmarks and rich local culture. And down at St. Michaels, there's no shortage of opportunities to sail away to the perfect day on the water. With all of these quaint qualities, it's no wonder why Maryland is such an adorable state.
