12 Storybook Towns In Maryland
Wherever you are in Maryland, you are never far from a storybook town. Out in Western Maryland's rugged Appalachian Mountains, you can enjoy one of the region's most scenic lakes by boat or by golf club in McHenry. Near Washington, D.C., you can go horseback riding and wine tasting at a down-home countryside town in Poolesville. On the Chesapeake Bay, there's also the proudly nautical resort town of St. Michaels with a museum that maintains its own floating fleet of historic ships. The 12 towns below offer experiences and settings straight out of a fairytale.
Cumberland
Perched on the banks of the Potomac River, roughly 140 miles south of Pittsburgh, sits the verdant and vibrant town of Cumberland. The historic city center holds treasures like the Allegany Museum, which preserves the region's history from pre-colonization times through the development of the C&O Canal and the railroads. Speaking of the railroad, the Western Maryland Scenic Railroad follows the tracks of the original Western Maryland Railway (chartered in 1852) and runs passengers on a scenic ride through the Appalachian wilderness. Back in town, visitors can explore Cumberland's contemporary arts scene at the C. William Gilchrist Museum of the Arts. And for the wilder side, it's a short drive out to Rocky Gap State Park, with its 3,000-plus acres of mountain forests and the refreshing waters of Lake Habeeb.
Staying at the state park, travelers can also take advantage of Rocky Gap Casino, Resort & Golf. Beyond its full casino floor, the resort offers deluxe rooms and suites, on-site restaurants, and the Jack Nicklaus-designed Rocky Gap Golf Course.
McHenry
Near the far western end of Maryland, about 45 miles northeast of Morgantown (West Virginia), sits the quaint village of McHenry on the shores of Deep Creek Lake. Deep Creek Lake State Park provides the perfect launchpad for boating, fishing, camping, hiking, and biking. For golfers, Thousand Acres Golf Club offers 18 holes with prime lake views. If you crave more excitement in Western Maryland's Appalachian backcountry, Herrington Manor State Park offers hiking, biking, kayaking, and swimming, and the connected lands of Potomac-Garrett State Forest provide plenty more trails to experience this verdant hardwood forest.
Once folks are ready to return to town, they can check into Cove Creek Lodge, a recently renovated hotel that pairs upscale boutique comfort with the warmth of an authentic countryside lodge.
Hancock
Squeezed in between the Pennsylvania and West Virginia state lines at the narrowest point of Maryland is the curious mountain town of Hancock. To the west, Green Ridge State Forest is Maryland's largest continuous expanse of public land at 49,000 acres and a wonderful corner of the Appalachian Ridge and Valley Province to hike and bike. Closer to town, the Sideling Hill Creek Preserve (managed by The Nature Conservancy) and nearby scenic pull-offs offer spectacular Potomac River valley views and chances to spot native wildlife, including bats, butterflies, and freshwater mussels. Heading east, Fort Frederick State Park preserves one of the largest British Colonial-era stone military fortifications in the country (completed in 1758 during the French and Indian War) and includes a boat launch and a stretch of flat water for easier canoeing.
Whatever folks decide to do in and around Hancock, they can stop at Blue Goose Market for local treats like Amish fudge, artisan jellies and jams, and house-baked pies. For more local hospitality, the 1828 Riverrun Bed & Breakfast offers five private suites, an on-site hot tub and sauna, and secure bike storage.
Brunswick
Brunswick may be a tiny Maryland town sandwiched between the monumental West Virginia town of Harpers Ferry and the storied wine country of Northern Virginia's Loudoun County, but it would be a mistake to pass by this lovely riverside village. The Appalachian Trail passes through a particularly striking corner of wilderness at Weverton Cliffs, where cliffs rise about 500 feet above the Potomac River and offer panoramic views. Continuing north, Gathland State Park preserves the home of Civil War-era journalist George Alfred Townsend and part of the Battle of South Mountain battlefield from 1862. Back in town, the Brunswick Heritage Museum features a 1,700-square-foot HO-scale model railroad and exhibits on how the B&O Railroad and C&O Canal shaped the area. A few blocks away, Smoketown Brewing transforms a historic fire station into a hotspot for local craft beer and hearty pub food.
Whether one comes to Brunswick for the natural wilderness or the historic landmarks, the Holiday Inn Express & Suites Brunswick makes a convenient base with welcome amenities like hot breakfast, an indoor saltwater pool, and a 24-hour fitness center.
Poolesville
Out in Montgomery County sits a country town so lush and laid back that it's hard to believe Poolesville is only about 35 miles from Washington, D.C. Visitors can make their way to Rocklands Farm Winery to take in the idyllic setting of this locally run farm and taste their low-intervention varietals. For more local fare, Locals Farm Market is a must-stop for hearty breakfast and lunch fare and a lineup of local craft beers. Meanwhile, Royce Hanson Conservation Park at Broad Run is perfect for stretching out and appreciating this expanse of lush forested wetlands and restored meadow habitat. And at Woodstock Equestrian Special Park, folks can go horseback riding on 16 miles of dedicated equestrian and hiking trails.
When guests are ready to wrap up for the day, the Town and Country Getaway vacation rental offers peace and quiet, along with fast WiFi, a fully stocked kitchen, and a pet-friendly environment.
Westminster
Situated on Maryland's Piedmont Plateau, about 37 miles northwest of Baltimore, is the surprisingly flavorful town of Westminster. This is a great place to launch a journey along the Carroll Wine Trail (with a designated driver) and discover tasty treasures like Old Westminster Winery, a family-run establishment crafting terroir-driven wines paired with farm-to-table cuisine. Also nearby is Serpent Ridge Vineyard, a boutique winery specializing in handcrafted, small-lot varietals like Chambourcin, Cabernet Franc, Seyval Blanc, and Vidal Blanc. Even in town, it's easy to stumble upon delicacies like the craft cocktails and wood-fired pizzas at Liquid Library and Maryland-style soul food at Collision Course.
To make a Carroll County wine country getaway a little extra special, guests can indulge in an easygoing stay at Sunday Morning at Savannah's. The boutique inn has a cozy coffee lounge, well-appointed guest rooms, and a spa menu of massage and acupuncture treatments.
Havre de Grace
Where the Susquehanna River reaches the northern tip of Chesapeake Bay, about 69 miles southwest of Philadelphia, Havre de Grace offers a unique perspective on Maryland history and culture. In the heart of town is the Concord Point Lighthouse, built in 1827 and one of the oldest lighthouses still in operation in Maryland, with many of its original materials and finishings preserved. Just steps away, the Havre de Grace Decoy Museum is dedicated to the area's longtime tradition of crafting decoys for waterfowl hunting. The Havre de Grace Colored School Museum and Cultural Center preserves Harford County's original early-20th-century public school that provided high-school education for African-American students, and continues as a critical hub for local Black culture. Returning to the waterfront, Millard Tydings Memorial Park is ideal for family playtime or simply watching the boats sail by, with its own boat ramp for anyone who wants to set sail.
After a full day exploring around the bay, it's a pleasant trek up to the Spencer Silver Mansion, a historic home now functioning as a boutique bed-and-breakfast with guest rooms furnished in elaborate period antiques.
St. Michaels
It's a roughly 51-mile journey from Annapolis across Chesapeake Bay to reach St. Michaels, and the town's maritime culture and bayside beauty make the trip worthwhile. A key highlight is the Chesapeake Bay Maritime Museum, an interactive hub for nautical culture that includes a working shipyard, the 1879 Hooper Strait Lighthouse (relocated to the museum grounds), and a floating fleet of historic ships that continue to sail. For another shoreline view, the St. Michaels Nature Trail stretches about 1.3 miles for scenic hiking and biking. For a different taste of St. Michaels, St. Michaels Winery showcases Maryland-made wines and cheeses, while Talbot St. Tavern serves locally sourced seafood, spirits, and craft beers.
For the full St. Michaels experience, guests can splurge on a stay at the Inn at Perry Cabin. This waterfront luxury resort offers elegant rooms and suites, on-site restaurants, the full-service Spa at Perry Cabin, access to Links at Perry Cabin, and a private fleet of motorboats and yachts.
Chesapeake Beach
Just 34 miles southeast of Washington, D.C., travelers will reach the cool and cozy waterfront village of Chesapeake Beach. The Chesapeake Beach Railway Museum preserves the town's 1898 railway station era, and the idyllic Fishing Creek corridor (including the Chesapeake Beach Railway Trail) offers hiking, biking, fishing, and birdwatching. For a fuller day at the bay, the nearby North Beach Pier features a sandy beach, a fishing pier, a boardwalk, and publicly available boat slips. Back in town, Tyler's Tackle Shop carries fishing supplies and runs its own Crab House for customers who prefer to pick up freshly caught local seafood.
To make a beach trip even better, the Inn at Herrington Harbour offers a private beach great for kayaking, paddleboarding, swimming, and sunbathing, along with rooms and suites, gardens with a two-mile eco-trail, and on-site dining.
Cambridge
Cambridge sits on the banks of the Choptank River on Maryland's Eastern Shore at the crossroads of American history and natural splendor. For much of the 19th century, Cambridge served as a critical stop on the Underground Railroad that Black Americans utilized to escape slavery. The Harriet Tubman Museum & Educational Center is worth visiting to learn more about Dorchester County native Harriet Tubman (born nearby around 1822) and the abolitionist movement she led, and the Harriet Tubman Underground Railroad National Historical Park just outside town provides more perspective on the environment Tubman came from. For an even deeper view of the area's natural environment, visitors can explore Blackwater National Wildlife Refuge, a critical bald eagle nesting area and sanctuary for migratory birds along the Atlantic Flyway. West of the refuge, Taylors Island Wildlife Management Area protects 1,100-plus acres of tidal marshes that provide habitat for white-tailed deer, fox squirrels, mallard ducks, and egrets.
For the full Cambridge experience, guests can stay at the waterfront Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina. Guests can tee off at the 18-hole River Marsh Golf Course, relax at the Sago Spa, make use of the 150-slip marina, and rest at the hotel's rooms and suites.
Smith Island
Maryland has a number of interesting and unique destinations, and none may be quite as unique as Smith Island, a community in the middle of Chesapeake Bay that is accessible only by boat. On the boat ride over, travelers can take in the tidal marshlands of Martin National Wildlife Refuge, home to northern diamondback terrapins, American black ducks, and great blue herons. On land, the island is always cooking up something good at local businesses like Smith Island Bakery, the go-to destination for the multi-layer Smith Island cake that is officially Maryland's state dessert (recognized in 2008). The main village of Ewell has Harborside Restaurant & Grocery for dining in and grab-and-go food, and Bayside Inn Restaurant for Maryland seafood classics like crab cakes, soft-shell crabs, and fried oysters.
To make a Smith Island getaway even better, Susan's on Smith Island welcomes guests to a locally owned bed-and-breakfast with home-style rooms and a full breakfast every morning that includes locally caught seafood.
Ocean City
Just south of the Delaware state line, Ocean City is Maryland's own fun-loving beach town. In the historic downtown, the Ocean City Boardwalk is a nearly three-mile stretch of family-friendly shops, eateries, and theme-park-style activities along the oceanfront. A short drive west, Isle of Wight Park offers a quieter side of the region and an idyllic natural retreat for kayaking, canoeing, fishing, and crabbing. Also in the area, golfers can play up to 18 holes at Eagle's Landing Golf Course, a serene course set at the edge of Sinepuxent Bay. And a little farther south, Assateague State Park has two miles of Atlantic Ocean beaches perfect for surfing, swimming, and surf fishing. It is also a great spot to look out for Assateague Island's famed wild horses.
There is a lot to experience around Ocean City, but it is also easy to settle down at The Hotels at Fager's Island. Centrally located near the Ocean City Expressway and the Midtown beaches, the resort feels like a secluded waterfront sanctuary with bay-view rooms and suites, the Fager's Island restaurant, and a stunning bayfront pool area.
Write Your Own Story While Visiting These Maryland Towns
Thanks to Maryland's East Coast geography, the state packs a surprising variety of towns into a compact footprint. Ocean City extends across a glorious stretch of Atlantic coast, St. Michaels is a stately resort town where the sailing is always smooth, and Cambridge combines Harriet Tubman's home country with Chesapeake marshland. Shifting inland, Westminster is wine country with farm-to-table dining, while Poolesville provides a countryside break just a short drive from the nation's capital. Heading into the mountains, Hancock opens up to Maryland's largest public lands, and Cumberland serves as a welcoming gateway to Appalachian culture and nature. With so many distinct options across a relatively small state, it's easy to see why Maryland is sometimes called "America in Miniature."
