30 days in Maryland Itinerary

30 days in Maryland Itinerary

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

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Ocean City — 5 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.
Step off the beaten path and head to Northside Park and OC Massage. Change things up with these side-trips from Ocean City: Salisbury (Salisbury Zoo & Ward Museum of Wildfowl Art). Next up on the itinerary: head outdoors with Outdoor Activities, admire the majestic nature at Assateague State Park, take in the waterfront at Ocean City Boardwalk, and tee off at Rum Pointe Seaside Golf Links.

For photos, more things to do, traveler tips, and other tourist information, refer to the Ocean City trip maker.

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 slightly colder nights when traveling from New York City in November since evenings lows in Ocean City dip to 39°F. Finish your sightseeing early on the 6th (Sat) to allow enough time to drive to Cambridge.
Parks · Outdoors · Museums · Wildlife
Side Trips

Cambridge — 5 nights

Cambridge is a city in Dorchester County, Maryland, United States. Explore hidden gems such as Blackwater National Wildlife Refuge and Harriet Tubman Museum and Educational Center. Venture out of the city with trips to St. Michaels (Chesapeake Bay Maritime Museum, 1879 Hooper Strait Lighthouse, &more). There's still lots to do: get engrossed in the history at Harriet Tubman Underground Railroad National Historical Park and look for gifts at The Amish Market.

For maps, photos, more things to do, and other tourist information, refer to the Cambridge trip planning website.

Traveling by car from Ocean City to Cambridge takes 1.5 hours. In November in Cambridge, expect temperatures between 57°F during the day and 39°F at night. Finish your sightseeing early on the 11th (Thu) so you can travel to Solomons.
Museums · Breweries & Distilleries · Wildlife · Shopping
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. Discover out-of-the-way places like Calvert Marine Museum and Drum Point Lighthouse and "On Watch" Monument. You'll find plenty of places to visit near Solomons: Forrest Hall Farm & Orchard (in Mechanicsville), Bruce Snake Gabrielson's Surf Art Gallery and Museum (in Chesapeake Beach) and Historic Port Tobacco Village (in Port Tobacco). There's lots more to do: go for a stroll along the water at Spring Cove Marina, brush up on your military savvy at Patuxent River Naval Air Museum, and take in the exciting artwork at Annmarie Garden.

To find traveler tips, more things to do, photos, and more tourist information, you can read our Solomons day trip planner.

You can drive from Cambridge to Solomons in 2.5 hours. In November, daytime highs in Solomons are 58°F, while nighttime lows are 40°F. Wrap up your sightseeing on the 15th (Mon) early enough to travel to Cumberland.
Museums · Parks · Historic Sites · Shopping
Side Trips

Cumberland — 6 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. Eschew the tourist crowds and head to Paw Paw Tunnel and Gordon-Roberts House. Get out of town with these interesting Cumberland side-trips: Swallow Falls State Park (in Oakland), C&O Canal Trust (in Hagerstown) and FireFly Farms Market (in Accident). Next up on the itinerary: make a trip to Allegany Fairgrounds, brush up on your knowledge of spirits at Charis Winery & Distillery, explore the landscape on two wheels at Great Allegheny Passage, and try to win big at Rocky Gap Casino Resort.

For more things to do, photos, reviews, and more tourist information, refer to the Cumberland road trip app.

You can drive from Solomons to Cumberland in 3.5 hours. Traveling from Solomons in November, plan for little chillier nights in Cumberland, with lows around 34°F. Finish your sightseeing early on the 21st (Sun) to allow enough time to drive to Baltimore.
Parks · Nature · Trails · Outdoors
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.
Eschew the tourist crowds 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: Havre de Grace Promenade (in Havre de Grace), Conowingo Dam (in Darlington) and Frederick (Weinberg Center for the Arts & Historic Downtown Frederick). The adventure continues: admire the masterpieces at Baltimore Museum of Art, take in the spiritual surroundings of The Baltimore Basilica, explore the galleries of B&O Railroad Museum, and wander the streets of Annapolis Historic District.

To see reviews, maps, where to stay, and other tourist information, use the Baltimore day trip planning app.

Traveling by car from Cumberland to Baltimore takes 2.5 hours. Expect somewhat warmer evenings in Baltimore when traveling from Cumberland in November, with lows around 43°F. Finish your sightseeing early on the 30th (Tue) so you can take a train back home.
Historic Sites · Museums · Parks · 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.