30 days in Maryland Itinerary

30 days in Maryland Itinerary

Created using Inspirock Maryland trip itinerary planner
Make it your trip
Drive
1
Ocean City
— 5 nights
Drive
2
Cambridge
— 5 nights
Drive
3
Stevensville, Kent Island
— 2 nights
Drive
4
Solomons
— 4 nights
Drive
5
Cumberland
— 4 nights
Drive
6
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 Oceanic Fishing Pier. Venture out of the city with trips to Salisbury (Salisbury Zoo, Ward Museum of Wildfowl Art, &more). And it doesn't end there: see the interesting displays at Ocean City Life-Saving Station Museum, sample the tasty concoctions at Burley Oak Brewing Company, don't miss a visit to Main Street Berlin, and look for all kinds of wild species at Ayers Creek Adventures.

To see other places to visit, where to stay, ratings, and more tourist information, read our Ocean City online trip itinerary 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. Traveling from New York City in November, expect a bit cooler with lows of 39°F in Ocean City. Finish your sightseeing early on the 6th (Sat) to allow enough time to drive to Cambridge.
Parks · Outdoors · Tours · 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 (Lyon Rum Distillery, Spas, &more). There's more to do: get engrossed in the history at Harriet Tubman Underground Railroad National Historical Park and look for gifts at The Amish Market.

For where to stay, reviews, maps, and more tourist information, go to the Cambridge online road trip planner.

Traveling by car from Ocean City to Cambridge takes 1.5 hours. In November, daily temperatures in Cambridge can reach 57°F, while at night they dip to 39°F. Cap off your sightseeing on the 11th (Thu) early enough to go by car to Stevensville.
Museums · Breweries & Distilleries · Shopping · Wineries
Side Trips

Stevensville, Kent Island — 2 nights

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. Start off your visit on the 12th (Fri): trek along Terrapin Nature Park and then brush up on your knowledge of spirits at Blackwater Distilling & Tavern. On the next day, get answers to all your questions at Chesapeake Heritage & Visitors Center and then stroll through Matapeake Clubhouse and Beach.

To see photos, other places to visit, traveler tips, and tourist information, use the Stevensville tour website.

You can drive from Cambridge to Stevensville in an hour. In November, plan for daily highs up to 55°F, and evening lows to 41°F. Wrap up your sightseeing by early afternoon on the 13th (Sat) to allow time for the car ride to Solomons.
Parks · Outdoors · Trails · Breweries & Distilleries
Side Trip

Solomons — 4 nights

Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. Eschew the tourist crowds and head to Calvert Marine Museum and Drum Point Lighthouse and Annmarie Garden. Step out of Solomons with an excursion to Janes Island State Park in Crisfield--about 1h 15 min away. There's much more to do: brush up on your military savvy at Patuxent River Naval Air Museum, trek along Flag Ponds Nature Park, admire the majestic nature at Calvert Cliffs State Park, and take an in-depth tour of Historic St. Mary's City.

To see reviews, other places to visit, where to stay, and more tourist information, you can read our Solomons vacation app.

Getting from Stevensville to Solomons by car takes about 2 hours. In November, daily temperatures in Solomons can reach 58°F, while at night they dip to 40°F. Finish up your sightseeing early on the 17th (Wed) so you can travel to Cumberland.
Parks · Museums · Nature · Trails
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. Eschew the tourist crowds and head to Paw Paw Tunnel and FireFly Farms Market. Get out of town with these interesting Cumberland side-trips: Swallow Falls State Park (in Oakland) and C&O Canal Trust (in Hagerstown). The adventure continues: don't miss a visit to Sideling Hill Welcome Center, try your luck at Rocky Gap Casino Resort, explore the landscape on two wheels at Great Allegheny Passage, and admire the majestic nature at Rocky Gap State Park.

For ratings and tourist information, read our Cumberland tour itinerary planner.

Getting from Solomons to Cumberland by car takes about 3.5 hours. Traveling from Solomons in November, expect a bit cooler with lows of 34°F in Cumberland. Finish up your sightseeing early on the 21st (Sun) so you can go by car to Baltimore.
Parks · Nature · Trails · Shopping
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.
Discover out-of-the-way places like Baltimore Museum of Art and B&O Railroad Museum. Explore Baltimore's surroundings by going to Catoctin Mountain Park (in Thurmont), Susquehanna State Park (in Havre de Grace) and Frederick (Carroll Creek Linear Park, National Museum of Civil War Medicine, &more). Next up on the itinerary: take in the spiritual surroundings of The Baltimore Basilica, find something for the whole family at The Adventure Park at Sandy Spring, enjoy breathtaking views from Top of the World Observation Level, and contemplate the waterfront views at Ego Alley.

For traveler tips, where to stay, other places to visit, and tourist information, read Baltimore planning site.

Traveling by car from Cumberland to Baltimore takes 2.5 hours. Plan for somewhat warmer nights when traveling from Cumberland in November since evenings lows in Baltimore dip to 43°F. Finish your sightseeing early on the 30th (Tue) to allow enough time 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.