30 days in Maryland Itinerary

30 days in Maryland Itinerary

Created using Inspirock Maryland trip planner
Make it your trip
Drive
1
Ocean City
— 4 nights
Drive
2
Cambridge
— 4 nights
Drive
3
Solomons
— 4 nights
Drive
4
Cumberland
— 4 nights
Drive
5
Hagerstown
— 4 nights
Drive
6
Baltimore
— 9 nights
Train

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Ocean City — 4 nights

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.
You'll discover tucked-away gems like Northside Park and Fishing Charters & Tours. Get out of town with these interesting Ocean City side-trips: Salisbury (Ben's Red Swings Community Playground, Salisbury Zoo, &more). And it doesn't end there: see the interesting displays at Ocean City Life-Saving Station Museum, indulge your thirst for a good beer at Burley Oak Brewing Company, take in the waterfront at Ocean City Boardwalk, and admire the majestic nature at Assateague State Park.

To find where to stay, photos, ratings, and other tourist information, refer to the Ocean City itinerary planning website.

New York City to Ocean City is an approximately 4.5-hour car ride. You can also do a combination of flight and bus; or do a combination of train, flight, and shuttle. Plan for a bit cooler nights when traveling from New York City in November since evenings lows in Ocean City dip to 39°F. Wrap up your sightseeing on the 5th (Fri) early enough to drive to Cambridge.
Parks · Outdoors · Wildlife · Tours
Side Trips

Cambridge — 4 nights

Cambridge is a city in Dorchester County, Maryland, United States. Step off the beaten path and head to Blackwater National Wildlife Refuge and Harriet Tubman Museum and Educational Center. Explore Cambridge's surroundings by going to St. Michaels (Spas, Chesapeake Bay Maritime Museum, &more) and Easton (Tuckahoe Steam and Gas Association & The Third Haven Friends Meeting House). There's still lots to do: get engrossed in the history at Harriet Tubman Underground Railroad National Historical Park, do a tasting at Layton's Chance Vineyard and Winery, admire the masterpieces at Academy Art Museum, and stop by The Amish Market.

To find ratings, other places to visit, more things to do, and tourist information, you can read our Cambridge tour builder site.

You can drive from Ocean City to Cambridge in 1.5 hours. In November, daily temperatures in Cambridge can reach 57°F, while at night they dip to 39°F. Wrap up your sightseeing on the 9th (Tue) early enough to travel to Solomons.
Museums · Breweries & Distilleries · Historic Sites · Spas
Side Trips

Solomons — 4 nights

Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. Step off the beaten path and head to Calvert Marine Museum and Drum Point Lighthouse and "On Watch" Monument. Explore the numerous day-trip ideas around Solomons: Historic Port Tobacco Village (in Port Tobacco), Maryland Veterans Memorial Museum (in Newburg) and Forrest Hall Farm & Orchard (in Mechanicsville). There's lots more to do: take in the waterfront activity at Spring Cove Marina, indulge your thirst for a good beer at Scorpion Brewing, admire the masterpieces at Bruce Snake Gabrielson's Surf Art Gallery and Museum, and take an in-depth tour of Historic St. Mary's City.

To see other places to visit, traveler tips, and more tourist information, refer to the Solomons trip builder.

You can drive from Cambridge to Solomons in 2.5 hours. Expect a daytime high around 58°F in November, and nighttime lows around 40°F. Finish up your sightseeing early on the 13th (Sat) so you can travel to Cumberland.
Museums · Parks · Historic Sites · Shopping
Side Trips

Cumberland — 4 nights

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. Step off the beaten path and head to Paw Paw Tunnel and Allegany Fairgrounds. Venture out of the city with trips to FireFly Farms Market (in Accident), Oakland (Deep Creek Lake State Park, Garrett County Historical Museum, &more) and The Discovery Center (in Swanton). There's lots more to do: steep yourself in history at Gordon-Roberts House, explore the landscape on two wheels at Green Ridge State Forest, do a tasting at Charis Winery & Distillery, and stroll through Great Allegheny Passage.

For other places to visit, traveler tips, more things to do, and other tourist information, go to the Cumberland trip itinerary maker website.

You can drive from Solomons to Cumberland in 3.5 hours. Plan for a bit cooler nights when traveling from Solomons in November since evenings lows in Cumberland dip to 34°F. Wrap up your sightseeing on the 17th (Wed) to allow time to drive to Hagerstown.
Parks · Nature · Historic Sites · Museums
Side Trips

Hagerstown — 4 nights

Hagerstown is a city in Washington County, Maryland, United States. You'll explore the less-touristy side of things at National Museum of Civil War Medicine and Historic Downtown Frederick. Explore the numerous day-trip ideas around Hagerstown: Sugarloaf Mountain (in Dickerson), Frederick (Carroll Creek Linear Park, Weinberg Center for the Arts, &more) and Lancaster County Dutch Market (in Germantown). There's still lots to do: contemplate the waterfront views at C&O Canal Trust, take in the spiritual surroundings of National Shrine of St. Elizabeth Ann Seton, contemplate the long history of Tolson's Chapel, and hike along Catoctin Mountain Park.

For more things to do, maps, reviews, and tourist information, you can read our Hagerstown tour itinerary planner.

Traveling by car from Cumberland to Hagerstown takes 1.5 hours. November in Hagerstown sees daily highs of 54°F and lows of 37°F at night. Wrap up your sightseeing on the 21st (Sun) early enough to drive to Baltimore.
Parks · Historic Sites · Nature · Museums
Side Trips

Baltimore — 9 nights

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 Fort McHenry National Monument and Historic Shrine and The Walters Art Museum. Get out of town with these interesting Baltimore side-trips: Fishpaws Marketplace (in Arnold), Annapolis (Annapolis Historic District, U.S. Naval Academy, &more) and Havre de Grace (Havre de Grace Promenade & Susquehanna State Park). And it doesn't end there: explore the world behind art at Baltimore Museum of Art, steep yourself in history at B&O Railroad Museum, wander the streets of Fell's Point, and find something for the whole family at The Adventure Park at Sandy Spring.

Ask Inspirock to suggest an itinerary and make planning a trip to Baltimore fast, fun, and easy.

Traveling by car from Hagerstown to Baltimore takes 1.5 hours. Plan for a bit warmer nights when traveling from Hagerstown in November since evenings lows in Baltimore dip to 43°F. Wrap up your sightseeing on the 30th (Tue) early enough to take a train back home.
Parks · Historic Sites · Museums · Nature
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.