17 days in Maryland Itinerary

17 days in Maryland Itinerary

Created using Inspirock Maryland trip itinerary planner

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Route & dates

17 days in Maryland Itinerary

Start: New York City
Drive:  4​h 30​min
1
Ocean City
— 2 nights
Drive:  1​h 45​min
2
St. Michaels
— 3 nights
Drive:  2​h 15​min
3
Solomons
— 2 nights
Drive:  3​h 30​min
4
Cumberland
— 2 nights
Drive:  1​h 30​min
5
Sharpsburg
— 3 nights
Drive:  1​h 30​min
6
Baltimore
— 4 nights
train:  2​h 45​min
End: New York City

2
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.
You'll find plenty of places to visit near Ocean City: Salisbury (Ben's Red Swings Community Playground & Ward Museum of Wildfowl Art). And it doesn't end there: enjoy the sand and surf at Ocean City Beach, play a few rounds at Rum Pointe Seaside Golf Links, examine the collection at Ocean City Life-Saving Station Museum, and stroll around Northside Park.

Ask Inspirock to suggest an itinerary and make planning a trip to Ocean City fast, fun, and easy.

New York City to Ocean City is an approximately 4.5-hour car ride. You can also do a combination of train and flight; or do a combination of train and bus. Expect a daytime high around 69°F in October, and nighttime lows around 53°F. Wrap up your sightseeing on the 14th (Mon) to allow time to drive to St. Michaels.

Things to do in Ocean City

Parks Outdoors Museums

Side Trips

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

3
nights
St. Michaels

St. Michaels ©
Get out of town with these interesting St. Michaels side-trips: Lead Dog Charters (in Stevensville), Annapolis (Susan Campbell Park & Wild Bird Center) and Cambridge (Choptank River Lighthouse & Neild Museum and Herb Garden).

To find photos, other places to visit, reviews, and other tourist information, read our St. Michaels trip itinerary planner.

Traveling by car from Ocean City to St. Michaels takes 2 hours. Alternatively, you can take a bus. October in St. Michaels sees daily highs of 70°F and lows of 53°F at night. Finish your sightseeing early on the 17th (Thu) so you can drive to Solomons.

Things to do in St. Michaels

Museums Parks Outdoors

Side Trips

Annapolis, Cambridge, Chestertown, Spas & Wellness, Lead Dog Charters
Highlights from your plan
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
Lyon Distilling Company ©
Lyon Distilling Company
1879 Hooper Strait Lighthouse ©
1879 Hooper Strait Lighthouse

2
nights
Solomons

Solomons ©
Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. On the 18th (Fri), sample the tasty concoctions at Scorpion Brewing, then admire the masterpieces at Bruce Snake Gabrielson's Surf Art Gallery and Museum, and then look for all kinds of wild species at Blackwater National Wildlife Refuge. On your second day here, explore the galleries of Calvert Marine Museum and Drum Point Lighthouse, take an in-depth tour of Jefferson Patterson Park & Museum, and then experience rural life at P.A. Bowen Farmstead.

To find traveler tips, other places to visit, and tourist information, read our Solomons trip app .

Getting from St. Michaels to Solomons by car takes about 2.5 hours. In October, daily temperatures in Solomons can reach 70°F, while at night they dip to 53°F. Finish up your sightseeing early on the 19th (Sat) so you can travel to Cumberland.

Things to do in Solomons

Museums Parks Wildlife

Side Trips

P.A. Bowen Farmstead, Bruce Snake Gabrielson's Surf Art Gallery and Museum, Blackwater National Wildlife Refuge, Jefferson Patterson Park & Museum, Scorpion Brewing
Highlights from your plan
Jefferson Patterson Park & Museum ©
Jefferson Patterson Park & Museum
P.A. Bowen Farmstead ©
P.A. Bowen Farmstead

2
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. Start off your visit on the 20th (Sun): look for gifts at FireFly Farms, learn about winemaking at Charis Winery, and then explore the landscape on two wheels at Great Allegheny Passage. Here are some ideas for day two: immerse yourself in nature at New Germany State Park, get lost in a book at Allegany County Library System - Frostburg Library, and then contemplate the long history of Paw Paw Tunnel.

Inspirock's itinerary builder makes planning a Cumberland trip simple and quick.

Getting from Solomons to Cumberland by car takes about 3.5 hours. Traveling from Solomons in October, you can expect nighttime temperatures to be slightly colder in Cumberland, with lows of 47°F. Wrap up your sightseeing on the 21st (Mon) early enough to drive to Sharpsburg.

Things to do in Cumberland

Parks Trails Outdoors

Side Trips

FireFly Farms, Allegany County Library System - Frostburg Library, New Germany State Park
Highlights from your plan
New Germany State Park ©
New Germany State Park
Paw Paw Tunnel ©
Paw Paw Tunnel

3
nights
Sharpsburg

Sharpsburg ©
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Get out of town with these interesting Sharpsburg side-trips: Penn Mar Park (in Cascade), C&O Canal Hike at Point of Rocks Boat Ramp (in Point of Rocks) and Roddy Road Covered Bridge (in Thurmont). There's much more to do: witness the site of a historic battle at Antietam National Battlefield, explore the different monuments and memorials at Rose Hill Cemetery, hike along Maryland Heights Trail, and brush up on your knowledge of spirits at Dragon Distillery, LLC.

To see more things to do, where to stay, reviews, and more tourist information, read Sharpsburg trip planner.

You can drive from Cumberland to Sharpsburg in 1.5 hours. October in Sharpsburg sees daily highs of 68°F and lows of 46°F at night. Finish up your sightseeing early on the 24th (Thu) so you can go by car to Baltimore.

Things to do in Sharpsburg

Parks Historic Sites Trails

Side Trips

Frederick, Knoxville, Roddy Road Covered Bridge, Rose Hill Cemetery, Penn Mar Park
Highlights from your plan
Clue IQ: An Escape Room Experience ©
Antietam National Battlefield ©
Antietam National Battlefield
Penn Mar Park ©
Penn Mar Park

4
nights
Baltimore

Baltimore ©
A major center for tourism and travel, Baltimore is famous as the city where amateur poet Francis Scott Key wrote the lyrics for the United States' national anthem.
You'll find plenty of places to visit near Baltimore: Diehl's Produce Market (in Severna Park) and Annapolis (Annapolis Historic District & U.S. Naval Academy). There's much more to do: try to win big at Horseshoe Casino, go for a stroll along the water at Inner Harbor, explore the world behind art at The Walters Art Museum, and identify plant and animal life at Loch Raven Reservoir.

To find other places to visit, traveler tips, ratings, and other tourist information, read our Baltimore trip itinerary site .

Traveling by car from Sharpsburg to Baltimore takes 1.5 hours. Traveling from Sharpsburg in October, plan for a bit warmer nights in Baltimore, with lows around 55°F. Finish your sightseeing early on the 28th (Mon) to allow enough time to take a train back home.

Things to do in Baltimore

Parks Historic Sites Neighborhoods

Side Trips

Annapolis, Diehl's Produce Market, Loch Raven Reservoir
Highlights from your plan
Sagamore Spirit Distillery ©
Sagamore Spirit Distillery
Horseshoe Casino ©
Horseshoe Casino

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