28 days in Maryland Itinerary

28 days in Maryland Itinerary

Created using Inspirock Maryland travel route maker

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Route & dates

28 days in Maryland Itinerary

Start: Nairobi
Fly + Drive:  22​h
1
Owings Mills
— 4 nights
Drive:  1​h 15​min
2
Havre de Grace
— 4 nights
Drive:  2​h 45​min
3
Ocean City
— 5 nights
Drive:  1​h 45​min
4
St. Michaels
— 4 nights
Drive:  3​h 30​min
5
Cumberland
— 4 nights
Drive:  1​h 30​min
6
Frederick
— 5 nights
Drive + Fly:  21​h
End: Nairobi

4
nights
Owings Mills

Owings Mills ©
Owings Mills is an unincorporated community and census-designated place in Baltimore County, Maryland, United States. Explore Owings Mills' surroundings by going to Baltimore (Sagamore Spirit Distillery, Fort McHenry National Monument and Historic Shrine, & more). The adventure continues: try your luck at Horseshoe Casino, examine the collection at American Visionary Art Museum, pause for some serene contemplation at Saint Alphonsus Church, and admire the masterpieces at The Walters Art Museum.

For where to stay, reviews, other places to visit, and tourist information, go to the Owings Mills road trip planning tool .

Nairobi, Kenya to Owings Mills is an approximately 22-hour combination of flight and car. Traveling from Nairobi to Owings Mills, you'll gain 8 hours due to the time zone difference. Expect cooler temperatures when traveling from Nairobi in December; daily highs in Owings Mills reach 11°C and lows reach 3°C. Wrap up your sightseeing on the 25th (Wed) to allow time to travel to Havre de Grace.

Things to do in Owings Mills

Parks Historic Sites Museums

Side Trip

Baltimore
Find places to stay Dec 21 — 25:
Highlights from your plan
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. Venture out of the city with trips to Casey Michelle Charters (in Stevensville), Jerusalem Mill and Village (in Kingsville) and Earleville (Painted Sky Alpaca Farm & Fiber Mill & Mount Harmon Plantation). There's lots more to do: take a leisurely stroll along Havre de Grace Promenade, identify plant and animal life at Anita C. Leight Estuary Center, stroll around Fisherman’s Park, and sample the tasty concoctions at Independent Brewing Company.

To see other places to visit, photos, more things to do, and tourist information, you can read our Havre de Grace day trip planner .

Traveling by car from Owings Mills to Havre de Grace takes an hour. In December, daily temperatures in Havre de Grace can reach 9°C, while at night they dip to 0°C. Finish your sightseeing early on the 29th (Sun) so you can travel to Ocean City.

Things to do in Havre de Grace

Parks Museums Outdoors

Side Trips

Bel Air, Earleville, Casey Michelle Charters, Upper Bay Museum, Anita C. Leight Estuary Center
Find places to stay Dec 25 — 29:
Highlights from your plan
Painted Sky Alpaca Farm & Fiber Mill ©
Havre de Grace Decoy Museum ©
Havre de Grace Decoy Museum
Susquehanna Museum at the Lock House ©

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.
Get out of town with these interesting Ocean City side-trips: Salisbury (Coco's Funhouse, Ward Museum of Wildfowl Art, & more) and Snow Hill (Furnace Town Living Heritage Village & Bishop's Stock Fine Art, Craft & Wine). There's lots more to do: take in the waterfront at Ocean City Boardwalk, walk around Northside Park, enjoy the sand and surf at Ocean City Beach, and have some family-friendly fun at Ocean City Screams Haunted House.

To find photos, ratings, more things to do, and more tourist information, use the Ocean City tour website .

Getting from Havre de Grace to Ocean City by car takes about 3 hours. Expect a daytime high around 12°C in December, and nighttime lows around 1°C. Wrap up your sightseeing on the 3rd (Fri) to allow time to drive to St. Michaels.

Things to do in Ocean City

Parks Historic Sites Museums

Side Trips

Salisbury, Berlin, Snow Hill
Find places to stay Dec 29 — Jan 3:
Highlights from your plan
Ocean City Boardwalk ©
Ocean City Boardwalk
Ocean City Beach ©
Ocean City Beach
Northside Park ©
Northside Park

4
nights
St. Michaels

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

Plan my St. Michaels trip by asking Inpirock to come up with tips and suggestions.

You can drive from Ocean City to St. Michaels in 2 hours. Another option is to take a bus. January in St. Michaels sees daily highs of 7°C and lows of -2°C at night. Finish up your sightseeing early on the 7th (Tue) so you can travel to Cumberland.

Things to do in St. Michaels

Museums Neighborhoods Parks

Side Trips

Annapolis, Cambridge, Bruce Snake Gabrielson's Surf Art Gallery and Museum, Harriet Tubman Underground Railroad National Historical Park, Spas & Wellness
Find places to stay Jan 3 — 7:
Highlights from your plan
U.S. Naval Academy ©
U.S. Naval Academy
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
Lyon Distilling Company ©
Lyon Distilling Company

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. Venture out of the city with trips to Schoolhouse Earth (in Friendsville), Simon Pearce Factory Outlet and Glassblowing (in Mountain Lake Park) and Oakland (Swallow Falls State Park, Garrett County Museum of Transportation, & more). Next up on the itinerary: hike along Great Allegheny Passage, see the interesting displays at Allegany Museum, browse the collection at Allegany County Library System - Washington Street Library, and contemplate the long history of Gordon-Roberts House.

To see traveler tips, maps, other places to visit, and other tourist information, use the Cumberland trip planner.

Traveling by car from St. Michaels to Cumberland takes 3.5 hours. In January in Cumberland, expect temperatures between 5°C during the day and -4°C at night. Wrap up your sightseeing on the 11th (Sat) early enough to travel to Frederick.

Things to do in Cumberland

Museums Parks Trails

Side Trips

Oakland, Schoolhouse Earth, Allegany County Library System - Frostburg Library, Dans Rock Scenic Overlook, Simon Pearce Factory Outlet and Glassblowing
Find places to stay Jan 7 — 11:
Highlights from your plan

5
nights
Frederick

Frederick ©
Frederick is a city and the county seat of Frederick County in the U.S. You'll find plenty of places to visit near Frederick: Emmitsburg (National Shrine Grotto of Lourdes & National Fallen Firefighters Memorial), Heavy Metal Playground (in Boonsboro) and Sharpsburg (Antietam National Battlefield & Tolson's Chapel). There's lots more to do: test your problem-solving skills at Clue IQ: An Escape Room Experience, go for a walk through Historic Downtown Frederick, make a trip to John Hanson National Memorial, and sample the fine beverages at Dragon Distillery, LLC.

To find traveler tips, maps, other places to visit, and tourist information, go to the Frederick itinerary planner .

You can drive from Cumberland to Frederick in 1.5 hours. In January, daytime highs in Frederick are 5°C, while nighttime lows are -5°C. Finish your sightseeing early on the 16th (Thu) to allow enough time to travel back home.

Things to do in Frederick

Historic Sites Parks Nature

Side Trips

Emmitsburg, Sharpsburg, Thurmont, Lockhouse 49 - C&O Canal Trust, Heavy Metal Playground
Find places to stay Jan 11 — 16:
Highlights from your plan
Clue IQ: An Escape Room Experience ©
Antietam National Battlefield ©
Antietam National Battlefield
Historic Downtown Frederick ©
Historic Downtown Frederick

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