58 days in Maryland Itinerary

58 days in Maryland Itinerary

Created using Inspirock Maryland travel planner

Plan created by another user.Make it yours

Route & dates

1
Cumberland
— 6 nights
2
Sharpsburg
— 8 nights
3
Rockville
— 8 nights
4
Baltimore
— 9 nights
5
Havre de Grace
— 8 nights
6
St. Michaels
— 8 nights
7
Ocean City
— 10 nights

6
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. Get out of town with these interesting Cumberland side-trips: McHenry (Funland & Wisp Resort), Green Ridge State Forest (in Flintstone) and Oakland (Deep Creek Lake State Park, Bill's Marine Service - Day Rentals, &more). Next up on the itinerary: explore the landscape on two wheels at Great Allegheny Passage, try to win big at Rocky Gap Casino Resort, look for gifts at FireFly Farms, and learn about winemaking at Charis Winery.

To find other places to visit, traveler tips, reviews, and other tourist information, read our Cumberland trip itinerary maker.

Washington DC to Cumberland is an approximately 2.5-hour car ride. Traveling from Washington DC in August, expect little chillier with lows of °F in Cumberland. Finish up your sightseeing early on the 9th (Thu) so you can go by car to Sharpsburg.

Things to do in Cumberland

Parks Outdoors Nature

Side Trips

Oakland, Grantsville, McHenry, Flintstone, National Road & Toll House
Highlights from your plan
Great Allegheny Passage ©
Great Allegheny Passage
Charis Winery ©
Charis Winery
Swallow Falls State Park ©
Swallow Falls State Park

8
nights
Sharpsburg

Sharpsburg ©
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Explore Sharpsburg's surroundings by going to Frederick (National Museum of Civil War Medicine, C. Burr Artz Public Library, &more), Thurmont (Loy's Station Covered Bridge & Cunningham Falls State Park) and Speedway (in Hagerstown). On the 10th (Fri), spend a day delving into the history of Antietam National Battlefield. Spend the 16th (Thu) exploring nature at C&O Canal Trust. And it doesn't end there: contemplate the waterfront views at Antietam Creek, stop by Blue Goose Fruit Market & Bakery, do a tasting at Big Cork Vineyards, and see the interesting displays at Hagerstown Roundhouse Museum.

For reviews, traveler tips, photos, and more tourist information, refer to the Sharpsburg tour itinerary maker tool.

Getting from Cumberland to Sharpsburg by car takes about 1.5 hours. In August, daytime highs in Sharpsburg are °F, while nighttime lows are °F. Wrap up your sightseeing on the 17th (Fri) to allow time to drive to Rockville.

Things to do in Sharpsburg

Parks Nature Historic Sites

Side Trips

Frederick, Hagerstown, Boonsboro, Thurmont, Big Cork Vineyards
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
Clue IQ: An Escape Room Experience ©
Clue IQ: An Escape Room Experience
C&O Canal Trust ©
C&O Canal Trust

8
nights
Rockville

Rockville ©
Rockville is a city located in the central region of Montgomery County, Maryland. Get out of town with these interesting Rockville side-trips: Greenbelt National Park (in Greenbelt), Montpelier Mansion (in Laurel) and Bowie (Six Flags America & Allen Pond Park). Pack the 18th (Sat) with family-friendly diversions at The Adventure Park at Sandy Spring. There's still lots to do: tee off at Worthington Manor Golf Club, contemplate the long history of Audubon Naturalist Society Woodend Sanctuary, stop by Saint Ignatius Church, and admire the majestic nature at Seneca Creek State Park.

To find traveler tips, maps, and other tourist information, refer to the Rockville trip builder site.

Getting from Sharpsburg to Rockville by car takes about 1.5 hours. In August in Rockville, expect temperatures between °F during the day and °F at night. Finish your sightseeing early on the 25th (Sat) to allow enough time to drive to Baltimore.

Things to do in Rockville

Parks Theme Parks Outdoors

Side Trips

Bowie, Port Tobacco, Waverly Street Gallery, The Adventure Park at Sandy Spring, Worthington Manor Golf Club
Highlights from your plan
Seneca Creek State Park ©
Seneca Creek State Park
The Adventure Park at Sandy Spring ©
The Adventure Park at Sandy Spring
Worthington Manor Golf Club ©
Worthington Manor Golf Club

9
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.
Explore the numerous day-trip ideas around Baltimore: Annapolis (Maryland State House, Hammond-Harwood House, &more), Ladew Topiary Gardens (in Monkton) and Oregon Ridge Park (in Cockeysville). The adventure continues: try to win big at Horseshoe Casino, wander the streets of Fell's Point, explore the world behind art at Baltimore Museum of Art, and see where the action happens at Oriole Park at Camden Yards.

To see photos, traveler tips, more things to do, and other tourist information, you can read our Baltimore route planner.

Traveling by car from Rockville to Baltimore takes an hour. Traveling from Rockville in August, plan for somewhat warmer nights in Baltimore, with lows around °F. Finish your sightseeing early on the 3rd (Mon) to allow enough time to drive to Havre de Grace.

Things to do in Baltimore

Parks Historic Sites Neighborhoods

Side Trips

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

8
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. Explore the numerous day-trip ideas around Havre de Grace: Bel Air (Harford Mall & Liriodendron Mansion), Elkton (West Meadow Park, Patriots Glen National Golf Club, &more) and Rocks State Park (in Jarrettsville). There's lots more to do: tee off at Bulle Rock Golf Club, catch a live event at Ripken Stadium, get outside with Schooner Sultana, and look for gifts at Book Plate.

To see other places to visit, reviews, traveler tips, and tourist information, use the Havre de Grace tour itinerary builder website.

Drive from Baltimore to Havre de Grace in an hour. Traveling from Baltimore in September, expect a bit cooler with lows of °F in Havre de Grace. Finish up your sightseeing early on the 11th (Tue) so you can travel to St. Michaels.

Things to do in Havre de Grace

Parks Outdoors Museums

Side Trips

Elkton, Chestertown, Bel Air, Aberdeen, Rising Sun
Highlights from your plan
Susquehanna State Park ©
Susquehanna State Park
Bulle Rock Golf Club ©
Bulle Rock Golf Club
Millard Tydings Memorial Park ©
Millard Tydings Memorial Park

8
nights
St. Michaels

St. Michaels ©
Get out of town with these interesting St. Michaels side-trips: Adkins Arboretum (in Ridgely), Prince Frederick (American Chestnut Land Trust & Second Looks Books) and Cambridge (Emily’s Produce, Blackwater National Wildlife Refuge, &more).

To find where to stay, other places to visit, traveler tips, and more tourist information, you can read our St. Michaels road trip site.

You can drive from Havre de Grace to St. Michaels in 2 hours. In September, plan for daily highs up to °F, and evening lows to °F. Wrap up your sightseeing on the 19th (Wed) to allow time to drive to Ocean City.

Things to do in St. Michaels

Outdoors Parks Shopping

Side Trips

Cambridge, Oxford, Chesapeake Beach, Prince Frederick, Martinak State Park
Highlights from your plan
American Chestnut Land Trust ©
American Chestnut Land Trust
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
Eastern Shore Food Tours - Eating Easton ©
Eastern Shore Food Tours - Eating Easton

10
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: Assateague Island National Seashore (in Assateague Island) and Salisbury (Arthur W. Perdue Stadium (Delmarva Shorebirds), Poplar Hill Mansion, &more). There's lots more to do: take a memorable tour with 48th St. Watersports, admire the majestic nature at Assateague State Park, stroll around Northside Park, and take in the waterfront at Ocean City Boardwalk.

To find reviews, maps, and more tourist information, read our Ocean City route maker tool.

Getting from St. Michaels to Ocean City by car takes about 2 hours. Other options: take a bus. In September, daily temperatures in Ocean City can reach °F, while at night they dip to °F. Finish your sightseeing early on the 29th (Sat) so you can drive back home.

Things to do in Ocean City

Parks Theme Parks Outdoors

Side Trips

Salisbury, Berlin, Assateague Island National Seashore
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
48th St. Watersports ©
48th St. Watersports
Ocean City Boardwalk ©
Ocean City Boardwalk

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