28 days in Maryland Itinerary

28 days in Maryland Itinerary

Created using Inspirock Maryland travel route maker

©
Plan created by another user. Make it yours

Route & dates

1
Owings Mills
— 4 nights
2
Havre de Grace
— 4 nights
3
Ocean City
— 5 nights
4
St. Michaels
— 4 nights
5
Cumberland
— 4 nights
6
Frederick
— 5 nights

4
nights
Owings Mills

Owings Mills ©
Owings Mills is an unincorporated community and census-designated place in Baltimore County, Maryland, United States. Venture out of the city with trips to Baltimore (Sagamore Spirit Distillery, Fort McHenry National Monument and Historic Shrine, &more). There's much more to do: observe the fascinating underwater world at National Aquarium, examine the collection at American Visionary Art Museum, brush up on your military savvy at Historic Ships in Baltimore, and take an in-depth tour of Baltimore Society of Model Engineers.

To see where to stay, traveler tips, reviews, and other tourist information, you can read our Owings Mills tour builder website.

Nairobi, Kenya to Owings Mills is an approximately 21.5-hour combination of flight and car. Due to the time zone difference, you'll gain 8 hours traveling from Nairobi to Owings Mills. Traveling from Nairobi in December, things will get colder in Owings Mills: highs are around °C and lows about °C. Finish your sightseeing early on the 25th (Wed) to allow enough time to travel to Havre de Grace.

Things to do in Owings Mills

Parks Historic Sites Museums

Side Trip

Baltimore
Highlights from your plan
Sagamore Spirit Distillery ©
Sagamore Spirit Distillery
National Aquarium ©
National Aquarium
Horseshoe Casino ©
Horseshoe Casino

4
nights
Havre de Grace

Havre de Grace ©
Havre de Grace, abbreviated HdG, is a city in Harford County, Maryland, situated at the mouth of the Susquehanna River and the head of Chesapeake Bay. Change things up with these side-trips from Havre de Grace: Jerusalem Mill and Village (in Kingsville), Earleville (Painted Sky Alpaca Farm & Fiber Mill & Mount Harmon Plantation) and Casey Michelle Charters (in Stevensville). The adventure continues: examine the collection at Lock House Museum, make a trip to Maryland House Travel Plaza, explore the landscape on two wheels at Ma and Pa Trail, and take in the waterfront at Havre de Grace Promenade.

To find other places to visit, ratings, where to stay, and more tourist information, read Havre de Grace day trip website.

Drive from Owings Mills to Havre de Grace in an hour. In December, plan for daily highs up to °C, and evening lows to °C. Cap off your sightseeing on the 29th (Sun) early enough to travel to Ocean City.

Things to do in Havre de Grace

Parks Museums Wildlife

Side Trips

Bel Air, Earleville, Gilpin's Falls Covered Bridge, Jerusalem Mill and Village, Upper Bay Museum
Highlights from your plan
Painted Sky Alpaca Farm & Fiber Mill ©
Painted Sky Alpaca Farm & Fiber Mill
Lock House Museum ©
Lock House Museum
Havre de Grace Decoy Museum ©
Havre de Grace Decoy Museum

5
nights
Ocean City

Ocean City ©
One of the country's favorite vacation resorts, Ocean City draws nearly 8 million visitors annually with its oceanfront boardwalk, clean beaches, and amusement parks.
Change things up with these side-trips from Ocean City: Snow Hill (Furnace Town Living Heritage Village & Bishop's Stock Fine Art, Craft & Wine) and Salisbury (Coco's Funhouse, Ward Museum of Wildfowl Art, &more). Next up on the itinerary: walk around Northside Park, get a taste of the local shopping with Flashback Old Time Photos, play a few rounds at Rum Pointe Seaside Golf Links, and enjoy the sand and surf at Ocean City Beach.

To see maps, where to stay, traveler tips, and more tourist information, use the Ocean City journey maker site.

Getting from Havre de Grace to Ocean City by car takes about 3 hours. December in Ocean City sees daily highs of °C and lows of °C at night. Cap off your sightseeing on the 3rd (Fri) early enough to go by car to St. Michaels.

Things to do in Ocean City

Historic Sites Parks Museums

Side Trips

Berlin, Salisbury, Snow Hill
Highlights from your plan
Ocean City Boardwalk ©
Ocean City Boardwalk
Northside Park ©
Northside Park
Ocean City Beach ©
Ocean City Beach

4
nights
St. Michaels

St. Michaels ©
Venture out of the city with trips to Cambridge (Blackwater National Wildlife Refuge & Choptank River Lighthouse), Bruce Snake Gabrielson's Surf Art Gallery and Museum (in Chesapeake Beach) and Annapolis (Annapolis Historic District, Chesapeake Light Craft, Inc., &more).

To find where to stay and more tourist information, you can read our St. Michaels road trip website.

You can drive from Ocean City to St. Michaels in 2 hours. Another option is to do a combination of bus and taxi. In January, plan for daily highs up to °C, and evening lows to °C. Finish your sightseeing early on the 7th (Tue) so you can travel to Cumberland.

Things to do in St. Michaels

Museums Neighborhoods Wildlife

Side Trips

Annapolis, Cambridge, Tilghman Watermans Museum, Harriet Tubman Underground Railroad National Historical Park, The Oxford Museum
Highlights from your plan
U.S. Naval Academy ©
U.S. Naval Academy
Lyon Rum Distillery & Tasting Room ©
Lyon Rum Distillery & Tasting Room
Annapolis Historic District
Annapolis Historic District

4
nights
Cumberland

Cumberland ©
Cumberland, officially the City of Cumberland, is a western gateway city and seat of Allegany County, Maryland, United States and the primary city of the Cumberland, MD-WV Metropolitan Statistical Area. Change things up with these side-trips from Cumberland: Oakland (Swallow Falls State Park, Garrett County Museum of Transportation, &more), Schoolhouse Earth (in Friendsville) and Simon Pearce Factory Outlet and Glassblowing (in Mountain Lake Park). Next up on the itinerary: grab your bike and head to Great Allegheny Passage, steep yourself in history at Gordon-Roberts House, take some stellar pictures from Dans Rock Scenic Overlook, and get lost in a book at Allegany County Library System - Washington Street Library.

For photos, where to stay, other places to visit, and more tourist information, use the Cumberland travel planning website.

Traveling by car from St. Michaels to Cumberland takes 3.5 hours. In January, daily temperatures in Cumberland can reach °C, while at night they dip to °C. Cap off your sightseeing on the 11th (Sat) early enough to travel to Frederick.

Things to do in Cumberland

Museums Parks Trails

Side Trips

Oakland, Allegany County Library System - Frostburg Library, Schoolhouse Earth, Dans Rock Scenic Overlook, Simon Pearce Factory Outlet and Glassblowing
Highlights from your plan
Great Allegheny Passage ©
Great Allegheny Passage
Allegany Museum ©
Allegany Museum
Gordon-Roberts House ©
Gordon-Roberts House

5
nights
Frederick

Frederick ©
Frederick is a city and the county seat of Frederick County in the U.S. Change things up with these side-trips from Frederick: Sharpsburg (Antietam National Battlefield & Tolson's Chapel), Emmitsburg (National Shrine Grotto of Lourdes & National Fallen Firefighters Memorial) and Heavy Metal Playground (in Boonsboro). The adventure continues: test your problem-solving skills at Clue IQ: An Escape Room Experience, get to know the fascinating history of Historic Downtown Frederick, sample the fine beverages at Dragon Distillery, LLC, and browse the collection at Thurmont Regional Library.

Find out how to plan Frederick trip without stress by asking Inspirock to help create an itinerary.

You can drive from Cumberland to Frederick in 1.5 hours. January in Frederick sees daily highs of °C and lows of °C at night. Wrap up your sightseeing on the 16th (Thu) early enough to travel back home.

Things to do in Frederick

Historic Sites Nature Parks

Side Trips

Thurmont, Sharpsburg, Emmitsburg, JUST LOOKIN' GALLERY, Lockhouse 49
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
Clue IQ: An Escape Room Experience ©
Clue IQ: An Escape Room Experience
Historic Downtown Frederick ©
Historic Downtown Frederick

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