14 days in Maryland Itinerary

14 days in Maryland Itinerary

Created using Inspirock Maryland trip itinerary maker

Plan created by another user. Make it yours
1
Cumberland
— 1 night
2
Sharpsburg
— 1 night
3
Baltimore
— 5 nights
4
St. Michaels
— 3 nights
5
Ocean City
— 3 nights

S M T W T F S
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10

1
night
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. Kick off your visit on the 25th (Fri): take some stellar pictures from Dans Rock Scenic Overlook, learn about winemaking at Charis Winery, and then trek along Great Allegheny Passage. Get ready for a full day of sightseeing on the 26th (Sat): stop by Hill Top Fruit Market, then explore the activities along Deep Creek Lake State Park, and then make a trip to Allegany Fairgrounds.

To see photos, maps, ratings, and tourist information, go to the Cumberland online trip itinerary builder.

Washington DC to Cumberland is an approximately 2.5-hour car ride. Traveling from Washington DC in September, expect little chillier with lows of 56°F in Cumberland. Finish up your sightseeing early on the 26th (Sat) so you can go by car to Sharpsburg.

Things to do in Cumberland

Parks · Outdoors · Trails · Nature

Side Trips

Highlights from your plan
Great Allegheny Passage ©
Great Allegheny Passage
Charis Winery ©
Charis Winery
Allegany Fairgrounds ©
Allegany Fairgrounds

1
night
Sharpsburg

Sharpsburg ©
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Start off your visit on the 27th (Sun): explore the striking landscape of Antietam National Battlefield.

To see traveler tips, other places to visit, and other tourist information, read our Sharpsburg trip planner.

Getting from Cumberland to Sharpsburg by car takes about 1.5 hours. In September, daily temperatures in Sharpsburg can reach 79°F, while at night they dip to 56°F. Cap off your sightseeing on the 27th (Sun) early enough to go by car to Baltimore.

Things to do in Sharpsburg

Nature · Historic Sites · Parks
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield

5
nights
Baltimore

Baltimore ©

City of Firsts

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.
Change things up with these side-trips from Baltimore: Big Escape Rooms (in Silver Spring), Waverly Street Gallery (in Bethesda) and Annapolis (Annapolis Historic District & U.S. Naval Academy). The adventure continues: try to win big at Horseshoe Casino, don't miss a visit to National Katyn Memorial, see the world from above with Charm City Helicopters, and get a new perspective on things with Boat Tours & Water Sports.

To see traveler tips, ratings, other places to visit, and tourist information, you can read our Baltimore trip itinerary tool.

Drive from Sharpsburg to Baltimore in 1.5 hours. Traveling from Sharpsburg in September, expect a bit warmer with lows of 66°F in Baltimore. Cap off your sightseeing on the 2nd (Fri) early enough to go by car to St. Michaels.

Things to do in Baltimore

Parks · Historic Sites · Nature · Neighborhoods

Side Trips

Highlights from your plan
Sagamore Spirit Distillery ©
Sagamore Spirit Distillery
Horseshoe Casino ©
Horseshoe Casino

3
nights
St. Michaels

St. Michaels ©
Explore St. Michaels' surroundings by going to Harriet Tubman Museum and Educational Center (in Cambridge), Harriet Tubman Underground Railroad National Historical Park (in Church Creek) and Schooner Sultana (in Chestertown).

For traveler tips, where to stay, more things to do, and other tourist information, read St. Michaels sightseeing planner.

Drive from Baltimore to St. Michaels in 2 hours. Alternatively, you can do a combination of bus and taxi. In October, plan for daily highs up to 70°F, and evening lows to 53°F. Finish up your sightseeing early on the 5th (Mon) so you can go by car to Ocean City.

Things to do in St. Michaels

Museums · Outdoors · Tours · Shopping

Side Trips

Highlights from your plan
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
Boat Tours & Water Sports
Lyon Rum Distillery & Tasting Room ©
Lyon Rum Distillery & Tasting Room

3
nights
Ocean City

Ocean City ©

The White Marlin Capital of the World

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: Salisbury (Salisbury Zoo & Ward Museum of Wildfowl Art). And it doesn't end there: take a leisurely stroll along Ocean City Boardwalk, tee off at Eagle's Landing Golf Course, tour the pleasant surroundings at Ocean City Beach, and stroll around Northside Park.

To find maps, more things to do, reviews, and more tourist information, use the Ocean City trip planner.

Traveling by car from St. Michaels to Ocean City takes 2 hours. Alternatively, you can do a combination of taxi and bus. In October, plan for daily highs up to 69°F, and evening lows to 53°F. Finish your sightseeing early on the 8th (Thu) to allow enough time to drive back home.

Things to do in Ocean City

Parks · Outdoors · Golf · Museums

Side Trips

Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Ocean City Boardwalk ©
Ocean City Boardwalk
OC Foodie Tour ©
OC Foodie Tour

Similar plans

15 days in Maryland BY A USER FROM CANADA August, kids, culture, fast-paced, popular sights Preferences: August, kids, culture Attraction style: Popular sights Pace: Fast-paced 53 days in United States BY A USER FROM UNITED STATES August, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife, fast-paced, popular & hidden gems Preferences: August, culture, outdoors, relaxing, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Fast-paced 42 days in United States BY A USER FROM UNITED STATES August, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife, fast-paced, popular & hidden gems Preferences: August, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife Attraction style: Popular & hidden gems Pace: Fast-paced 5 days in Maryland BY A USER FROM UNITED STATES September, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife, fast-paced, popular sights Preferences: September, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife Attraction style: Popular sights Pace: Fast-paced 7 days in Virginia & Maryland BY A USER FROM UNITED STATES June, teens, culture, relaxing, beaches, historic sites, museums, wildlife, extra slow, popular & hidden gems Preferences: June, teens, culture, relaxing, beaches, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Extra slow 20 days in United States BY A USER FROM UNITED KINGDOM February, kids, outdoors, relaxing, beaches, historic sites, slow & easy, popular sights Preferences: February, kids, outdoors, relaxing, beaches, historic sites Attraction style: Popular sights Pace: Slow & easy 7 days in Maryland BY A USER FROM UNITED STATES March, culture, outdoors, relaxing, historic sites, museums, wildlife, popular & hidden gems Preferences: March, culture, outdoors, relaxing, historic sites, museums, wildlife Attraction style: Popular & hidden gems Pace: Medium 3 days in Maryland BY A USER FROM UNITED STATES August, culture, outdoors, relaxing, romantic, museums, shopping, wildlife, popular sights Preferences: August, culture, outdoors, relaxing, romantic, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 17 days in Maryland & Florida Keys BY A USER FROM UNITED STATES December, teens, popular sights Preferences: December, teens Attraction style: Popular sights Pace: Medium 4 days in Maryland BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, popular & hidden gems Preferences: September, culture, outdoors, relaxing, romantic, beaches Attraction style: Popular & hidden gems Pace: Medium 7 days in United States BY A USER FROM UNITED STATES August, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife, hidden gems Preferences: August, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife Attraction style: Hidden gems Pace: Medium 7 days in United States BY A USER FROM UNITED STATES July, culture, outdoors, relaxing, romantic, historic sites, museums, slow & easy, popular & hidden gems Preferences: July, culture, outdoors, relaxing, romantic, historic sites, museums Attraction style: Popular & hidden gems Pace: Slow & easy
See more plans