24 days in Maryland Itinerary

24 days in Maryland Itinerary

Created using Inspirock Maryland trip itinerary planner

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Route & dates

24 days in Maryland Itinerary

Start: Philadelphia
Drive:  1​h 45​min
1
Havre de Grace
— 1 night
Drive:  1​h 45​min
2
St. Michaels
— 2 nights
Drive:  2​h
3
Ocean City
— 5 nights
Drive:  6​h 15​min
4
Oakland
— 3 nights
Drive:  2​h 45​min
5
Sharpsburg
— 2 nights
Drive:  1​h 15​min
6
Rockville
— 3 nights
Drive:  1​h 15​min
7
Baltimore
— 6 nights
train:  1​h 15​min
End: Philadelphia

1
night
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. Kick off your visit on the 27th (Fri): explore and take pictures at Ripken Stadium, then admire the majestic nature at Susquehanna State Park, and then examine the collection at Susquehanna Museum at the Lock House. Keep things going the next day: stroll through Millard Tydings Memorial Park, then snap pictures at Gilpins Covered Bridge, and then immerse yourself in nature at Rocks State Park.

To see where to stay, reviews, traveler tips, and tourist information, use the Havre de Grace road trip planner .

Philadelphia to Havre de Grace is an approximately 1.5-hour car ride. In July in Havre de Grace, expect temperatures between 86°F during the day and 70°F at night. Finish your sightseeing early on the 28th (Sat) so you can travel to St. Michaels.

Things to do in Havre de Grace

Parks Nature Museums

Side Trips

Ripken Stadium, Rocks State Park, Gilpin's Falls Covered Bridge
Highlights from your plan
Susquehanna State Park ©
Susquehanna State Park
Millard Tydings Memorial Park ©
Millard Tydings Memorial Park
Susquehanna Museum at the Lock House ©

2
nights
St. Michaels

St. Michaels ©
On the 29th (Sun), examine the collection at Chesapeake Bay Maritime Museum, get outside with Chesapeake Bay Environmental Center, and then look for gifts at The Preppy Redneck. Get ready for a full day of sightseeing on the next day: head outdoors with American Chestnut Land Trust, then experience rural life at Emily’s Produce, then don't miss a visit to Choptank River Lighthouse, and finally take in the exciting artwork at Ouvert Gallery.

Plan a trip to St. Michaels easily and quickly by telling Inspirock to suggest an itinerary.

Traveling by car from Havre de Grace to St. Michaels takes 2 hours. Expect a daytime high around 87°F in July, and nighttime lows around 71°F. Cap off your sightseeing on the 30th (Mon) early enough to go by car to Ocean City.

Things to do in St. Michaels

Outdoors Museums Shopping

Side Trips

Cambridge, American Chestnut Land Trust, Chesapeake Bay Environmental Center
Highlights from your plan
American Chestnut Land Trust ©
American Chestnut Land Trust
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
The Preppy Redneck ©
The Preppy Redneck

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.
Spend the 2nd (Thu) exploring nature at Assateague Island National Seashore. And it doesn't end there: choose your vessel at 48th St. Watersports, tee off at Eagle's Landing Golf Course, have some family-friendly fun at Ocean City Screams Haunted House, and enjoy the sand and surf at Ocean City Beach.

To see more things to do, reviews, photos, and tourist information, go to the Ocean City day trip planner .

Traveling by car from St. Michaels to Ocean City takes 2 hours. Alternatively, you can do a combination of taxi and shuttle; or do a combination of taxi and bus. July in Ocean City sees daily highs of 84°F and lows of 70°F at night. Finish up your sightseeing early on the 4th (Sat) so you can travel to Oakland.

Things to do in Ocean City

Parks Nature Outdoors

Side Trips

Assateague Island National Seashore, Assateague State Park
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Ocean City Boardwalk ©
Ocean City Boardwalk
Northside Park ©
Northside Park

3
nights
Oakland

Oakland ©
Oakland is a town in the west-central part of Garrett County, Maryland. You'll find plenty of places to visit near Oakland: Cumberland (Gordon-Roberts House & Great Allegheny Passage) and Grantsville (Hill Top Fruit Market & Spruce Forest Artisan Village). The adventure continues: immerse yourself in nature at Swallow Falls State Park, take an in-depth tour of The Oakland B&O Railroad Museum, hit the slopes at Wisp Resort, and contemplate the waterfront views at Deep Creek Lake State Park.

To find more things to do, reviews, photos, and tourist information, read our Oakland itinerary app .

You can drive from Ocean City to Oakland in 5.5 hours. Expect slightly colder temperatures when traveling from Ocean City in August; daily highs in Oakland reach 72°F and lows reach 57°F. Finish up your sightseeing early on the 8th (Wed) so you can travel to Sharpsburg.

Things to do in Oakland

Outdoors Parks Nature

Side Trips

Grantsville, Cumberland, Wisp Resort
Highlights from your plan
Lodestone Golf Course ©
Lodestone Golf Course
Swallow Falls State Park ©
Swallow Falls State Park
Deep Creek Lake State Park ©
Deep Creek Lake State Park

2
nights
Sharpsburg

Sharpsburg ©
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Start off your visit on the 9th (Thu): get to know the fascinating history of Antietam National Battlefield. Here are some ideas for day two: don't miss a visit to Gambrill State Park, then get lost in a book at C. Burr Artz Public Library, then get your game on at Clue IQ: An Escape Room Experience, and finally contemplate the waterfront views at Antietam Creek.

To see maps, traveler tips, ratings, and other tourist information, go to the Sharpsburg tour itinerary planner .

Traveling by car from Oakland to Sharpsburg takes 2.5 hours. Expect somewhat warmer weather when traveling from Oakland in August: highs in Sharpsburg hover around 84°F, while lows dip to 62°F. Cap off your sightseeing on the 10th (Fri) early enough to travel to Rockville.

Things to do in Sharpsburg

Parks Nature Historic Sites

Side Trip

Frederick
Highlights from your plan
Clue IQ: An Escape Room Experience ©
Antietam National Battlefield ©
Antietam National Battlefield
C. Burr Artz Public Library ©
C. Burr Artz Public Library

3
nights
Rockville

Rockville ©
Rockville is a city located in the central region of Montgomery County, Maryland. Explore Rockville's surroundings by going to Harborfront Area (in National Harbor) and Six Flags America (in Bowie). Pack the 11th (Sat) with family-friendly diversions at The Adventure Park at Sandy Spring. There's still lots to do: steep yourself in history at Audubon Naturalist Society Woodend Sanctuary, have some family-friendly fun at Monster Mini Golf, and get in on the family fun at Miniature Train and Carousel at Wheaton Regional Park.

For photos, reviews, maps, and more tourist information, read Rockville online trip maker .

Traveling by car from Sharpsburg to Rockville takes 1.5 hours. In August, daytime highs in Rockville are 83°F, while nighttime lows are 63°F. Wrap up your sightseeing on the 13th (Mon) to allow time to travel to Baltimore.

Things to do in Rockville

Theme Parks Parks Wildlife

Side Trips

The Adventure Park at Sandy Spring, Audubon Naturalist Society Woodend Sanctuary, Harborfront Area, Monster Mini Golf, Miniature Train and Carousel at Wheaton Regional Park
Highlights from your plan
The Adventure Park at Sandy Spring ©
The Adventure Park at Sandy Spring
Harborfront Area ©
Harborfront Area
Six Flags America ©
Six Flags America

6
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.
Venture out of the city with trips to Prigel Family Creamery (in Long Green), Annapolis (Maryland State House, Hammond-Harwood House, & more) and Ladew Topiary Gardens (in Monkton). Next up on the itinerary: try to win big at Horseshoe Casino, explore the world behind art at The Walters Art Museum, brush up on your knowledge of spirits at Sagamore Spirit Distillery, and take in the history at Fort McHenry National Monument.

Start your trip to Baltimore by creating a personalized itinerary on Inspirock.

You can drive from Rockville to Baltimore in an hour. Traveling from Rockville in August, expect somewhat warmer with lows of 71°F in Baltimore. Finish your sightseeing early on the 19th (Sun) to allow enough time to take a train back home.

Things to do in Baltimore

Parks Historic Sites Museums

Side Trips

Annapolis, Kinder Farm Park, Ladew Topiary Gardens
Highlights from your plan
Sagamore Spirit Distillery ©
Sagamore Spirit Distillery
Horseshoe Casino ©
Horseshoe Casino
Oriole Park at Camden Yards ©
Oriole Park at Camden Yards

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