22 days in Maryland & Chesapeake Itinerary

22 days in Maryland & Chesapeake Itinerary

Created using Inspirock United States route planner

Plan created by another user. Make it yours

Route & dates

1
Hagerstown
— 2 nights
2
Baltimore
— 5 nights
3
Ocean City
— 3 nights
4
Chesapeake
— 8 nights
5
Solomons
— 3 nights

2
nights
Hagerstown

Hagerstown ©
Hagerstown is a city in Washington County, Maryland, United States. Do your shopping at Pennsylvania Dutch Market and The Delaplaine Visual Arts Education Center. Do some cultural sightseeing at Antietam National Battlefield and JUST LOOKIN' GALLERY. Explore Hagerstown's surroundings by going to Historic Downtown Frederick (in Frederick) and C&O Canal Hike at Point of Rocks Boat Ramp (in Point of Rocks). There's still lots to do: learn about winemaking at Red Heifer Winery.

To find where to stay, other places to visit, reviews, and more tourist information, go to the Hagerstown day trip planner.

Washington DC to Hagerstown is an approximately 1.5-hour car ride. Expect slightly colder evenings in Hagerstown when traveling from Washington DC in June, with lows around 64°F. Finish up your sightseeing early on the 7th (Mon) so you can go by car to Baltimore.

Things to do in Hagerstown

Historic Sites · Parks · Nature

Side Trips

Frederick, Antietam National Battlefield, Red Heifer Winery, C&O Canal Hike at Point of Rocks Boat Ramp
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
Red Heifer Winery ©
Red Heifer Winery
Historic Downtown Frederick ©
Historic Downtown Frederick

5
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.
M/V Bay Breeze of Chesapeake City and Annapolis Historic District are good opportunities to explore the local culture. Head to Fell's Point and Diehl's Produce Marketfor some retail therapy. Change things up with these side-trips from Baltimore: Bohemia RIver (in Chesapeake City) and U.S. Naval Academy (in Annapolis). The adventure continues: try your luck at Horseshoe Casino, explore the galleries of Historic Ships in Baltimore, take in the architecture and atmosphere at Saint Alphonsus Church, and sample the fine beverages at Sagamore Spirit Distillery.

To see where to stay, ratings, reviews, and tourist information, use the Baltimore trip itinerary website.

Traveling by car from Hagerstown to Baltimore takes 1.5 hours. In June, daily temperatures in Baltimore can reach 85°F, while at night they dip to 69°F. Finish your sightseeing early on the 12th (Sat) to allow enough time to drive to Ocean City.

Things to do in Baltimore

Parks · Historic Sites · Nature

Side Trips

Chesapeake City, Annapolis, Diehl's Produce Market
Highlights from your plan
Sagamore Spirit Distillery ©
Sagamore Spirit Distillery
Horseshoe Casino ©
Horseshoe Casino
M/V Bay Breeze of Chesapeake City ©
M/V Bay Breeze of Chesapeake City

3
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.
Get a sense of the local culture at Art League of Ocean City and Layton's Chance Vineyard and Winery. Give yourself a bit of retail therapy at The Kite Loft and Bishop's Stock Fine Art, Craft & Wine. Step out of Ocean City to go to Princess Anne and see Boxwood Gardens, which is approximately 1 hour away. There's still lots to do: enjoy the sand and surf at Ocean City Beach, see the interesting displays at Ocean City Life-Saving Station Museum, take in the exciting artwork at Flashback Old Time Photos, and admire the majestic nature at Assateague State Park.

To see photos and more tourist information, read Ocean City tour itinerary site.

You can drive from Baltimore to Ocean City in 3 hours. Alternatively, you can take a bus. Traveling from Baltimore in June, expect nights in Ocean City to be about the same, around 65°F, while days are slightly colder, around 79°F. Wrap up your sightseeing on the 15th (Tue) early enough to travel to Chesapeake.

Things to do in Ocean City

Shopping · Museums · Parks

Side Trips

Berlin, Bishop's Stock Fine Art, Craft & Wine, Boxwood Gardens, Layton's Chance Vineyard and Winery
Highlights from your plan
The Kite Loft ©
The Kite Loft
Layton's Chance Vineyard and Winery ©
Layton's Chance Vineyard and Winery
Ocean City Beach ©
Ocean City Beach

8
nights
Chesapeake

Chesapeake ©
Chesapeake is an independent city in the Commonwealth of Virginia. Head to The Peanut Patch and OBX Art Studiofor some retail therapy. Your cultural itinerary includes sights like Vineyard Voyage and Whalehead Club. Change things up with these side-trips from Chesapeake: Nags Head (Jockey's Ridge State Park, Bodie Island Lighthouse, &more), Virginia Beach (Grommet Island Park, Tarnished Truth Distilling Company, &more) and Corolla (Back Country Safari Tours, Historic Corolla Chapel, &more). There's lots more to do: enjoy the sand and surf at Virginia Beach, contemplate the long history of Wright Brothers National Memorial, browse the different shops at Virginia Beach Antique Mall, and stroll around Oak Grove Lake Park.

Discover how to plan a Chesapeake trip in just a few steps with Inspirock's itinerary builder.

Drive from Ocean City to Chesapeake in 3 hours. When traveling from Ocean City in June, plan for a bit warmer days and about the same nights in Chesapeake: temperatures range from 85°F by day to 66°F at night. Finish your sightseeing early on the 23rd (Wed) so you can travel to Solomons.

Things to do in Chesapeake

Outdoors · Parks · Tours

Side Trips

Virginia Beach, Corolla, Nags Head, Kill Devil Hills, Vineyard Voyage
Highlights from your plan
Oak Grove Lake Park ©
Oak Grove Lake Park
Wright Brothers National Memorial ©
Wright Brothers National Memorial
Military Aviation Museum ©
Military Aviation Museum

3
nights
Solomons

Solomons ©
Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. Do some cultural sightseeing at Annmarie Garden and Hopkins Original Art. You'll find plenty of places to visit near Solomons: Historic Port Tobacco Village (in Port Tobacco) and St. Michaels (Lyon Rum Distillery & Tasting Room & Boat Tours & Water Sports). There's lots more to do: see the interesting displays at Calvert Marine Museum and Drum Point Lighthouse, expand your understanding of the military at "On Watch" Monument, get engrossed in the history at Historic St. Mary's City, and shop like a local with North End Gallery.

For other places to visit, traveler tips, photos, and more tourist information, read Solomons travel tool.

You can drive from Chesapeake to Solomons in 4 hours. In June, daytime highs in Solomons are 83°F, while nighttime lows are 66°F. Finish up your sightseeing early on the 26th (Sat) so you can go by car back home.

Things to do in Solomons

Museums · Shopping · Parks

Side Trips

St. Michaels, Leonardtown, Historic Port Tobacco Village, Jefferson Patterson Park & Museum, Historic St. Mary's City
Highlights from your plan
Annmarie Garden ©
Annmarie Garden
Jefferson Patterson Park & Museum ©
Jefferson Patterson Park & Museum

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