Shannon O'Brien Travel Itineraries

The best destinations

Ocean City, MD USA - October 6, 2018: Tourists walk along the southern tip of Ocean City Beach on the Atlantic Ocean in late afternoon on a sunny autumn day
Ocean City, MD USA - October 6, 2018: Tourists walk along the southern tip of Ocean City Beach on the Atlantic Ocean in late afternoon on a sunny autumn day

The Best of Maryland

#65 best destination in the world

Map view

Colonial Annapolis Historic District

Aerial view of Maryland State House capitol building white dome and state circle with colonial houses in  Annapolis on a sunny weekend afternoon

Best time to visit: April-May

  • The Colonial Annapolis Historic District is a designated historic area located in Annapolis
  • This district was established to preserve the architectural and historical significance of the area, particularly its well-preserved buildings from the colonial period
  • Annapolis is notable for having the highest concentration of 18th-century Georgian-style buildings in the United States
  • The district includes important structures such as the Maryland State House, which is the oldest state capitol still in continuous legislative use

Assateague Island National Seashore

Wild Ponies of the Assateague Island National Seashore, Maryland
  • Assateague Island National Seashore is a protected area spanning approximately across Maryland and Virginia
  • It is renowned for its diverse ecosystems, which include sandy beaches, salt marshes, maritime forests, and coastal bays
  • The seashore is particularly famous for its wild horses, which roam freely on the island, as well as its rich birdlife and recreational opportunities

Inner Harbor, Baltimore

Baltimore, MD, USA May 10 People enjoy a warm spring day walking on the waterfront at Inner Harbor, in Baltimore, Maryland

Best time to visit: June-Aug

  • The Inner Harbor is a historic seaport in Baltimore, that serves as a central hub for visitors, featuring a waterfront with scenic views, fresh seafood restaurants, and a variety of recreational activities
  • Once a thriving shipyard, the Inner Harbor has transformed into a major landmark and is considered one of America's oldest seaports
  • Visitors can enjoy muesums, dining, shopping, and various entertainment options, such as boat tours and waterfront events
  • The harbor features a brick promenade that allows for walks along the water

Fort McHenry, Baltimore

Fort McHenry from the air, Baltimore

Best time to visit: June-Aug

  • Fort McHenry is a historic coastal fort located in Baltimore
  • It is best known for its role during the War of 1812, particularly the Battle of Baltimore in September 1814
  • The fort successfully defended the city from a British naval attack, which inspired Francis Scott Key to write "The Star-Spangled Banner," the national anthem of the United States
  • Constructed in the early 1800s, Fort McHenry features a star-shaped design and was built to protect the entrance to Baltimore's harbor

Fell's Point, Baltimore

Baltimore, Maryland US - SEPTEMBER 25, 2022: Historic brick buildings along Thames street in downtown Fell's Point neighborhood restaurants and bars for dining

Best time to visit: June-Aug

  • Fell's Point is a historic waterfront neighborhood located in Baltimore
  • Established around 1763, it was originally founded by English shipbuilder William Fell and served as a significant shipbuilding center and deep-water port for the city
  • The neighborhood is known for its cobblestone streets, 18th-century architecture, and numerous restaurants, shops, and cultural attractions

Walters Art Museum, Baltimore

A chinese woman looking at a shelf of various vases within the walters art museum in baltimore maryland.

Best time to visit: June-Aug

  • The Walters Art Museum is a public art museum located in Baltimore
  • The collection includes over 36,000 objects that span more than 7,000 years, featuring a wide variety of artworks from different cultures around the world
  • The museum's collection encompasses various types of art, including ancient Asian art, textiles, jewelry, arms and armor, and 19th-century European paintings

Chesapeake and Ohio Canal Trail to Great Falls Overlook, Chesapeake and Ohio Canal National Historical Park

USA, Maryland, Great Falls, Potomac River.

Walk difficulty: easy

  • The Chesapeake and Ohio Canal Trail to Great Falls Overlook is a scenic hiking trail located within the Chesapeake and Ohio Canal National Historical Park near Potomac
  • The trail offers views along the canal and leads to the Great Falls Overlook, where visitors can enjoy vistas of the Great Falls on the Potomac River
  • The Chesapeake and Ohio Canal itself is a historically significant waterway that played a crucial role in transportation and commerce in the 19th century, and today it serves as a recreational area for hiking, biking, and exploring nature

Ocean City Beach

Ocean City, MD USA - October 6, 2018: Tourists walk along the southern tip of Ocean City Beach on the Atlantic Ocean in late afternoon on a sunny autumn day

Best time to visit: late May-early Sept

  • Ocean City Beach refers to the coastline located in Ocean City, which features a 10-mile stretch of pristine sandy beaches along the Atlantic Ocean
  • The beach is known for its clean, smooth sand and clear waters, making it ideal for sunbathing, swimming, and various beach sports
  • The area includes a boardwalk with numerous attractions, including arcades, restaurants, and shops

Ocean City Boardwalk

Ocean City, Maryland/United States- June 30th 2019: Boardwalk

Best time to visit: late May-early Sept

  • The Ocean City Boardwalk is a historic destination that stretches approximately 3 miles along the oceanfront
  • The boardwalk was first constructed in 1902 to provide a walkway for hotel guests to enjoy the ocean view
  • The boardwalk is lined with numerous attractions, including: restaurants and food stands, serving foods such as fries, ice cream, and caramel corn; amusement rides and arcade games; and a variety of shops offering everything from souvenirs to beach gear

Chesapeake Bay Maritime Museum, St. Michaels

Photo of shutterstock_2564326701
  • The Chesapeake Bay Maritime Museum, located in St. Michaels, is an institution dedicated to preserving the maritime history and culture of the Chesapeake Bay region
  • The museum houses the world's largest collection of Chesapeake Bay boats and offers a variety of interactive exhibits across its 35 buildings
  • The campus includes notable structures such as the 1879 Hooper Strait Lighthouse and a working shipyard where traditional craftsmanship is showcased
  • Situated along the Miles River, the museum offers scenic views and opportunities for river excursions

Swallow Falls Canyon Trail, Swallow Falls State Park

Swallow Falls State Park Canyon Trail Waterfall- Side angle

Walk difficulty: easy

  • Swallow Falls Canyon Trail is a scenic hiking trail located in Swallow Falls State Park, near Oakland
  • The trail offers access to the banks of the Youghiogheny River, and the terrain includes towering sandstone cliffs