22 days in Maryland & Chesapeake Itinerary

22 days in Maryland & Chesapeake Itinerary

Created using Inspirock United States route planner

Make it your trip
Drive
1
Hagerstown
— 2 nights
Drive
2
Baltimore
— 5 nights
Drive
3
Ocean City
— 3 nights
Drive
4
Chesapeake
— 8 nights
Drive
5
Solomons
— 3 nights
Drive

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Hagerstown

— 2 nights
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 Just LOOKIN' Gallery and Historic Downtown Frederick. Step out of Hagerstown to go to Point of Rocks and see C&O Canal Hike at Point of Rocks Boat Ramp, which is approximately 44 minutes away. There's more to do: witness the site of a historic battle at Antietam National Battlefield and learn about winemaking at Red Heifer Winery.

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

Washington DC to Hagerstown is an approximately 1.5-hour car ride. Plan for little chillier nights when traveling from Washington DC in June since evenings lows in Hagerstown dip to 64°F. Cap off your sightseeing on the 7th (Mon) early enough to go by car to Baltimore.

Things to do in Hagerstown

Historic Sites · Parks · Nature · Shopping

Side Trips

Baltimore

— 5 nights

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.
M/V Bay Breeze of Chesapeake City and Fell's Point are good opportunities to explore the local culture. Change things up with these side-trips from Baltimore: Diehl's Produce Market (in Severna Park), Bohemia RIver (in Chesapeake City) and Annapolis (Annapolis Historic District & U.S. Naval Academy). 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 · Museums

Side Trips

Ocean City

— 3 nights

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.
Satisfy your inner culture vulture at Art League of Ocean City and Bishop's Stock Fine Art, Craft & Wine. Change things up with these side-trips from Ocean City: Layton's Chance Vineyard and Winery (in Vienna) and Boxwood Gardens (in Princess Anne). The adventure continues: kick back and relax at Ocean City Beach, see the interesting displays at Ocean City Life-Saving Station Museum, play a few rounds at Rum Pointe Seaside Golf Links, and take a leisurely stroll along Ocean City Boardwalk.

To find reviews, ratings, other places to visit, and tourist information, you can read our Ocean City travel planner.

You can drive from Baltimore to Ocean City in 3 hours. Alternatively, you can take a bus. While traveling from Baltimore, expect a bit cooler days and about the same nights in Ocean City, ranging from highs of 79°F to lows of 65°F. Wrap up your sightseeing on the 15th (Tue) early enough to travel to Chesapeake.

Things to do in Ocean City

Shopping · Parks · Museums · Outdoors

Side Trips

Chesapeake

— 8 nights
Chesapeake is an independent city in the Commonwealth of Virginia. Head to The Peanut Patch and Virginia Beach Antique Mallfor some retail therapy. Your cultural itinerary includes sights like Vineyard Voyage and Wright Brothers National Memorial. Change things up with these side-trips from Chesapeake: Nags Head (Jockey's Ridge State Park, Bodie Island Lighthouse, &more), Corolla (Whalehead Club, Back Country Safari Tours, &more) and Virginia Beach (Grommet Island Park, Tarnished Truth Distilling Company, &more). There's lots more to do: kick back and relax at Virginia Beach, walk around Oak Grove Lake Park, and get a taste of the local shopping with OBX Art Studio.

To see where to stay, reviews, other places to visit, and other tourist information, read Chesapeake holiday planning tool.

Drive from Ocean City to Chesapeake in 3 hours. Traveling from Ocean City in June, you will find days in Chesapeake are a bit warmer (85°F), and nights are about the same (66°F). Wrap up your sightseeing on the 23rd (Wed) to allow time to travel to Solomons.

Things to do in Chesapeake

Outdoors · Parks · Tours · Museums

Side Trips

Solomons

— 3 nights
Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. Get some cultural insight at Annmarie Garden and North End Gallery. Get out of town with these interesting Solomons side-trips: Historic Port Tobacco Village (in Port Tobacco) and St. Michaels (Hopkins Original Art, Lyon Rum Distillery, &more). There's still lots to do: enjoy the sea views from Calvert Marine Museum and Drum Point Lighthouse, take an in-depth tour of Historic St. Mary's City, expand your understanding of the military at "On Watch" Monument, and immerse yourself in nature at Jefferson Patterson Park & Museum.

For photos, reviews, other places to visit, and other tourist information, read Solomons itinerary planning site.

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 your sightseeing early on the 26th (Sat) to allow enough time to drive back home.

Things to do in Solomons

Museums · Shopping · Historic Sites · Parks

Side Trips

Maryland travel guide

4.1
Casinos · Specialty Museums · Aquariums
The Old Line State
Perhaps best known as the birthplace of religious and political freedom in the United States, Maryland retains the spirit of colonial America, with stately 18th-century villages and historical landmarks. Although it's one of the nation's smallest states, there is no shortage of things to do here and you may find your itinerary fills up quickly. Make time in your vacation to tour Maryland's diverse landscape, which includes mountain peaks, picturesque Atlantic coastline, and the bustling city of Baltimore. Military buffs will enjoy touring the state's four Civil War Trails, where you can follow the footsteps of U.S. soldiers, or visiting the port city of Annapolis, home to the United States Naval Academy.