21 days in Maryland Itinerary

21 days in Maryland Itinerary

Created using Inspirock Maryland itinerary planner

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Route & dates

21 days in Maryland Itinerary

Start: Washington DC
Drive:  1​h 30​min
1
Solomons
— 2 nights
Drive:  3​h 30​min
2
Ocean City
— 6 nights
Drive:  1​h 45​min
3
St. Michaels
— 2 nights
Drive:  1​h
4
Stevensville, Kent Island
— 1 night
Drive:  1​h
5
Baltimore
— 6 nights
Drive:  3​h 15​min
6
Oakland
— 3 nights
Drive:  3​h 15​min
End: Washington DC

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. Calvert Marine Museum and Drum Point Lighthouse and Old Jail Museum are good opportunities to explore the local culture. Eschew the tourist crowds and head to Blackwater National Wildlife Refuge and Historic St. Mary's City. There's lots more to do: admire the natural beauty at Annmarie Garden, learn about all things military at Patuxent River Naval Air Museum, kick back and relax at Elms Beach Park, and stroll through Flag Ponds Nature Park.

To see where to stay, other places to visit, more things to do, and tourist information, you can read our Solomons driving holiday planner .

Washington DC to Solomons is an approximately 1.5-hour car ride. June in Solomons sees daily highs of 83°F and lows of 66°F at night. Cap off your sightseeing on the 12th (Fri) early enough to travel to Ocean City.

Things to do in Solomons

Museums Parks Outdoors

Side Trips

Lexington Park, Blackwater National Wildlife Refuge, Old Jail Museum, Historic St. Mary's City, Flag Ponds Nature Park
Highlights from your plan
Blackwater National Wildlife Refuge ©
Historic St. Mary's City ©
Historic St. Mary's City

6
nights
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.
Discover out-of-the-way places like Northside Park and Speed Boats Tours. Get some cultural insight at Ocean City Life-Saving Station Museum and Pemberton Historical Park. Change things up with these side-trips from Ocean City: Boxwood Gardens (in Princess Anne), Salisbury (Arthur W. Perdue Stadium (Delmarva Shorebirds), Ward Museum of Wildfowl Art, & more) and Janes Island State Park (in Crisfield). There's much more to do: see what you can catch with a fishing tour, glide through the air with a parasailing or paragliding tour, view the masterpieces at Flashback Old Time Photos, and admire the majestic nature at Assateague State Park.

To see traveler tips, maps, other places to visit, and more tourist information, use the Ocean City trip site .

Getting from Solomons to Ocean City by car takes about 3.5 hours. June in Ocean City sees daily highs of 79°F and lows of 65°F at night. Finish your sightseeing early on the 18th (Thu) so you can drive to St. Michaels.

Things to do in Ocean City

Outdoors Parks Tours

Side Trips

Berlin, Salisbury, Boxwood Gardens, Janes Island State Park
Highlights from your plan
Fishing Charters & Tours
Ward Museum of Wildfowl Art ©
Ward Museum of Wildfowl Art
Rum Pointe Seaside Golf Links ©
Rum Pointe Seaside Golf Links

2
nights
St. Michaels

St. Michaels ©
Kick off your visit on the 19th (Fri): see the interesting displays at The Oxford Museum, enjoy the sea views from 1879 Hooper Strait Lighthouse, indulge in some personalized pampering at some of the best spas, then indulge your thirst for a good beer at Eastern Shore Brewing, and finally sample the fine beverages at Lyon Distilling Company. Get ready for a full day of sightseeing on the 20th (Sat): get engrossed in the history at Harriet Tubman Underground Railroad National Historical Park, then take an in-depth tour of Harriet Tubman Museum and Educational Center, and then learn about winemaking at Layton's Chance Vineyard and Winery.

To see more things to do, where to stay, ratings, and more tourist information, refer to the St. Michaels road trip site .

Getting from Ocean City to St. Michaels by car takes about 2 hours. Other options: take a bus. In June in St. Michaels, expect temperatures between 84°F during the day and 66°F at night. Finish up your sightseeing early on the 20th (Sat) so you can go by car to Stevensville.

Things to do in St. Michaels

Museums Breweries & Distilleries Spas

Side Trips

Harriet Tubman Underground Railroad National Historical Park, Harriet Tubman Museum and Educational Center, Layton's Chance Vineyard and Winery, The Oxford Museum
Highlights from your plan

1
night
Stevensville, Kent Island

Stevensville ©
Stevensville is a census-designated place (CDP) in Queen Anne's County, Maryland, and is the county's most populous place among both CDPs and municipalities. On the 21st (Sun), trek along Quiet Waters Park, then steep yourself in history at Maryland State House, then contemplate the long history of William Paca Garden, and finally brush up on your knowledge of spirits at Blackwater Distilling & Tavern.

To find maps, ratings, photos, and more tourist information, use the Stevensville trip itinerary builder app .

Traveling by car from St. Michaels to Stevensville takes an hour. In June, daily temperatures in Stevensville can reach 82°F, while at night they dip to 67°F. Cap off your sightseeing on the 21st (Sun) early enough to go by car to Baltimore.

Things to do in Stevensville

Historic Sites Parks Outdoors

Side Trip

Annapolis
Highlights from your plan
Maryland State House ©
Maryland State House
Blackwater Distilling & Tavern ©
Blackwater Distilling & Tavern
William Paca Garden ©
William Paca Garden

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.
Step off the beaten path and head to Baltimore and Ohio Railroad Museum and Historic Downtown Frederick. Do some cultural sightseeing at Baltimore Museum of Art and Federal Hill Park. Change things up with these side-trips from Baltimore: Maryland House Travel Plaza (in Aberdeen), National Harbor (in National Harbor) and Boordy Vineyards (in Hydes). There's much more to do: brush up on your knowledge of spirits at Sagamore Spirit Distillery, admire the landmark architecture of Baltimore Pennsylvania Station, learn about winemaking at Linganore Winecellars, and sample the tasty concoctions at Guinness Open Gate Brewery & Barrel House.

To see photos, reviews, more things to do, and tourist information, read Baltimore trip planning website .

Traveling by car from Stevensville to Baltimore takes an hour. Expect a daytime high around 85°F in June, and nighttime lows around 69°F. Wrap up your sightseeing on the 27th (Sat) to allow time to travel to Oakland.

Things to do in Baltimore

Historic Sites Neighborhoods Breweries & Distilleries

Side Trips

Frederick, National Harbor, Boordy Vineyards, Rockville Town Square, Linganore Winecellars
Highlights from your plan
Sagamore Spirit Distillery ©
Sagamore Spirit Distillery
Historic Downtown Frederick ©
Historic Downtown Frederick
National Museum of Civil War Medicine ©

3
nights
Oakland

Oakland ©
Oakland is a town in the west-central part of Garrett County, Maryland. Paw Paw Tunnel and Spruce Forest Artisan Village are good opportunities to explore the local culture. You'll explore the less-touristy side of things at Swallow Falls State Park and Deep Creek Lake State Park. Change things up with these side-trips from Oakland: Cumberland (Rocky Gap State Park & Great Allegheny Passage), Dans Rock Scenic Overlook (in Midland) and Frostburg Depot (in Frostburg). There's more to do: stop by FireFly Farms.

To see where to stay, reviews, traveler tips, and other tourist information, use the Oakland trip planner .

You can drive from Baltimore to Oakland in 3.5 hours. Prepare for little chillier weather when traveling from Baltimore in June: high temperatures in Oakland hover around 70°F and lows are around 56°F. Finish your sightseeing early on the 30th (Tue) so you can travel back home.

Things to do in Oakland

Parks Nature Outdoors

Side Trips

Cumberland, Frostburg Depot, Spruce Forest Artisan Village, Dans Rock Scenic Overlook, FireFly Farms
Highlights from your plan
Swallow Falls State Park ©
Swallow Falls State Park
Spruce Forest Artisan Village ©
Spruce Forest Artisan Village
Paw Paw Tunnel ©
Paw Paw Tunnel

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