The Most Picturesque Towns In Maryland

With roughly 3,200 miles of shoreline, 16,800 miles of river, and more than 60 state parks, Maryland’s natural beauty extends far and wide. Its historic architecture is just as impressive, with 19th-century lighthouses, preserved log cabins, and federal-style homes now serving as museums, to name just a few. The following eight towns are some of the best representations of this beauty, leaving you with a fresh appreciation for everything the Old Line State has to offer.

St. Michaels

Sitting along the shores of the Chesapeake Bay, St. Michaels is a gorgeous harbor town with plenty of ways to enjoy the water. Travelers hoping to explore the bay can reserve a charter with Sail Selina II, which offers day sails, sunset champagne sails, wine tasting sails, and moonlight cruises, among other specialty excursions. Travelers can take in river views and local history on a Patriot Cruises tour, enjoying a 70-minute trip along the Miles River with narration about the area’s centuries-old mansions and wildlife. Once you find yourself on dry land again, make sure to stop by the 1879 Hooper Strait Lighthouse, a historic light that was built to help sailors navigate the tricky shoals of Hooper Strait.

Grantsville

Grantsville is famous for its rustic beauty, largely present in landmarks like the Casselman River Bridge and the Spruce Forest Artisan Village. While the Casselman River Bridge State Park is temporarily closed for construction, the artisan village remains open and welcoming visitors. Here, travelers will find a grouping of historic log cabins, now housing local artists, museums, and an operating 19th-century grist mill. The Savage River State Forest is also just 10 minutes south of town, featuring over 55,000 acres of mixed hardwood forest, hiking and biking trails, and a 230-acre reservoir for kayaking and canoeing. Right near the mouth of the reservoir, travelers can enjoy a scenic weekend of camping at Big Run State Park, a campground with 23 primitive campsites that are available year-round upon reservation.

Ocean City

With 10 miles of beaches, a boardwalk, and coastal parks, Ocean City makes the most of its prime spot along the shore. Travelers hoping to get outdoors can start their trip at Northside Park, the town’s largest park, spanning 58 acres and featuring various sports facilities, a foot bridge, a fishing lagoon, two piers, a gazebo, and more. Afterward, head over to the Ocean City Boardwalk, which has been rated as one of the best boardwalks in the country with three miles of shops, restaurants, and family-friendly activities. For a waterfront meal, grab lunch or dinner at the Angler Restaurant, a waterfront establishment with unbeatable views and fresh seafood.

Chestertown

Situated on the banks of the Chester River, Chestertown is a scenic riverside community with a bustling art scene. Those wanting to spend an afternoon on the river can book a cruise with Chester River Packet Company, which provides public evening, Saturday afternoon, and Sunday brunch cruises. The town is home to abundant historic architecture, and several inns allow visitors to experience it firsthand. One example is the Brampton 1860, a historic inn set on 35 acres of peaceful, pastoral land. If you are in town on the first Friday of the month, check out the town’s First Friday art walks, where shops and galleries stay open until 8 pm, promoting the local art scene.

Thurmont

Thurmont, which roughly translates to “Gateway to the Mountains,” is home to several notable parks and preserves. Southwest of town in the Catoctin Mountains lies Cunningham Falls State Park, which features a scenic lake, waterfall, campgrounds, and opportunities for swimming, canoeing, and hiking. Catoctin Mountain Park is also nearby, offering 25 miles of hiking trails, trout fishing streams, horseback riding, and camping. Families will also love visiting the Catoctin Wildlife Preserve, a 50-acre park consisting of lush landscaping, natural ponds, and a diverse array of wildlife, including monkeys, macaws, pythons, and panthers.

Berlin

If seeing a majestic herd of wild horses is on your bucket list, Berlin is the perfect travel destination for you. This town is located near the Assateague Island National Seashore, a National Park Service site with sandy beaches, maritime forests, coastal bays, and marshes. It is also famously home to the Assateague wild horse herd! After spending a day on the seashore, head back into town to check out some of the town’s iconic landmarks and art. The Calvin B. Taylor House Museum is a wonderful starting point, set in a federal-style home from 1832 that today exhibits the history of Berlin. Another highlight is the town’s Arts & Entertainment District, an official designation by the Maryland State Arts Council that features colorful murals, glassblowing studios, bookstores, galleries, and other artsy attractions.

Solomons

Solomons is a riverfront village at the mouth of the Patuxent River, rich in maritime history and natural beauty. Travelers can start their trip with a stroll along the Solomons Island Boardwalk, a waterfront promenade with unbeatable views of the Patuxent River. There are a couple of notable lighthouses in the area to check out as well, such as Drum Point Lighthouse, a well-preserved screwpile lighthouse that is now part of the Calvert Marine Museum. To learn more about the town’s history, sign up for a tour with Solomons Island Heritage Tours, which offers sunset river cruises that pass by some of the town’s most historic landmarks.

Oakland

With rivers, waterfalls, and lakes, Oakland offers nearly every type of natural attraction visitors might hope for. Swallow Falls State Park is a must-visit for any traveler, a mountain park with a 53-foot-tall waterfall, the rushing Youghiogheny River, and hemlock forests. Herrington Manor State Park is another beautiful park to add to your itinerary, covering 365 acres with a lake and plenty of opportunities for canoeing, kayaking, swimming, biking, and picnicking. If you are looking for a scenic place to spend the night, consider lodging at the Suites at Silver Tree, a luxury hotel right on the shores of Deep Creek Lake.

Final Thoughts

Maryland’s small size does not limit its beauty. These eight towns are evidence of that, offering everything you could hope for in a state of its size. Towns like Ocean City, St. Michaels, and Chestertown provide an unforgettable waterfront experience for travelers, while towns like Oakland and Thurmont are bursting with state parks and preserves. So get ready to experience the most picturesque corners of Maryland like never before with a visit to these eight towns!