30 days in Maryland Itinerary

30 days in Maryland Itinerary

Created using Inspirock Maryland itinerary maker
Make it your trip
Train
1
Baltimore
— 8 nights
Drive
2
Hagerstown
— 4 nights
Drive
3
Cumberland
— 4 nights
Drive
4
Oakland
— 3 nights
Unknown
5
Assateague Island
— 1 night
Unknown
6
Ocean City
— 4 nights
Drive
7
St. Michaels
— 5 nights
Fly

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Baltimore — 8 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.
Get out of town with these interesting Baltimore side-trips: The Awakening Sculpture (in National Harbor), Silver Spring (Silver Spring Civic Center & Wheaton Regional Park) and Lockhouse 10 (in Cabin John). Spend the 8th (Mon) exploring nature at Fort McHenry National Monument and Historic Shrine. There's much more to do: try your luck at Horseshoe Casino, admire the masterpieces at Baltimore Museum of Art, get up close and personal with brilliant marine life at National Aquarium, and visit Fell's Point.

To see ratings, where to stay, and other tourist information, go to the Baltimore trip builder site.

New York City to Baltimore is an approximately 3-hour train ride. You can also drive; or take a bus. Expect a daytime high around 57°F in November, and nighttime lows around 43°F. Finish up your sightseeing early on the 9th (Tue) so you can go by car to Hagerstown.
Parks · Museums · Historic Sites · Nature
Side Trips

Hagerstown — 4 nights

Hagerstown is a city in Washington County, Maryland, United States. You'll find plenty of places to visit near Hagerstown: Emmitsburg (National Shrine of St. Elizabeth Ann Seton, National Shrine Grotto of Lourdes, &more), Frederick (Weinberg Center for the Arts, Historic Downtown Frederick, &more) and Sugarloaf Mountain (in Dickerson). There's lots more to do: explore the striking landscape of C&O Canal Trust, contemplate the long history of Tolson's Chapel, explore the different monuments and memorials at Rose Hill Cemetery, and make a trip to Lockhouse 49.

To find traveler tips, where to stay, and other tourist information, read Hagerstown day trip planning tool.

Traveling by car from Baltimore to Hagerstown takes 1.5 hours. Traveling from Baltimore in November, you can expect nighttime temperatures to be slightly colder in Hagerstown, with lows of 37°F. Finish your sightseeing early on the 13th (Sat) so you can drive to Cumberland.
Historic Sites · Museums · Nature · Parks
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. Get out of town with these interesting Cumberland side-trips: Green Ridge State Forest (in Flintstone) and Grantsville (House of Yoder & New Germany State Park). The adventure continues: explore the landscape on two wheels at Great Allegheny Passage, don't miss a visit to Allegany Fairgrounds, steep yourself in history at Paw Paw Tunnel, and see the interesting displays at Allegany Museum.

To find ratings, reviews, photos, and more tourist information, use the Cumberland road trip planning site.

Drive from Hagerstown to Cumberland in 1.5 hours. In November in Cumberland, expect temperatures between 54°F during the day and 34°F at night. Finish your sightseeing early on the 17th (Wed) to allow enough time to drive to Oakland.
Outdoors · Parks · Historic Sites · Nature
Side Trips

Oakland — 3 nights

Oakland is a town in the west-central part of Garrett County, Maryland. Oakland is known for nature, adventure, and museums. Your trip includes some of its best attractions: see the interesting displays at Garrett County Museum of Transportation, look for gifts at FireFly Farms Market, admire the majestic nature at Herrington Manor State Park, and explore the engaging exhibits at The Discovery Center.

For other places to visit, ratings, photos, and other tourist information, use the Oakland trip itinerary builder.

Drive from Cumberland to Oakland in 1.5 hours. Traveling from Cumberland in November, expect nights in Oakland to be about the same, around 31°F, while days are little chillier, around 45°F. Wrap up your sightseeing on the 20th (Sat) to allow time to travel to Assateague Island.
Museums · Shopping · Parks · Nature
Side Trips

Assateague Island — 1 night

Kick off your visit on the 21st (Sun): explore the wealth of natural beauty at Assateague Island National Seashore.

For other places to visit, reviews, and tourist information, you can read our Assateague Island driving holiday planning website.

Use the Route module to find suitable travel options from Oakland to Assateague Island. Expect a bit warmer temperatures when traveling from Oakland in November; daily highs in Assateague Island reach 57°F and lows reach 39°F. Wrap up your sightseeing on the 21st (Sun) to allow time to travel to Ocean City.
Nature · Wildlife · Parks
Highlights from your trip

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 find plenty of places to visit near Ocean City: Snow Hill (Julia A. Purnell Museum & Bishop's Stock Fine Art, Craft & Wine) and Eastern Shore Baseball Hall of Fame Museum (in Salisbury). The adventure continues: stroll around Northside Park, play a few rounds at Rum Pointe Seaside Golf Links, enjoy the sand and surf at Ocean City Beach, and immerse yourself in nature at Assateague State Park.

For reviews, more things to do, traveler tips, and more tourist information, you can read our Ocean City day trip planning tool.

The Route module can help you plan travel from Assateague Island to Ocean City. November in Ocean City sees daily highs of 57°F and lows of 39°F at night. Finish your sightseeing early on the 25th (Thu) so you can drive to St. Michaels.
Outdoors · Parks · Museums · Wildlife
Side Trips

St. Michaels — 5 nights

Explore the numerous day-trip ideas around St. Michaels: Blackwater Distilling & Tavern (in Stevensville), Harriet Tubman Underground Railroad National Historical Park (in Church Creek) and Cambridge (Harriet Tubman Museum and Educational Center, Blackwater National Wildlife Refuge, &more).

To find maps, where to stay, traveler tips, and other tourist information, you can read our St. Michaels attractions site.

Drive from Ocean City to St. Michaels in 2 hours. Alternatively, you can do a combination of shuttle and taxi; or do a combination of bus and taxi. In November in St. Michaels, expect temperatures between 58°F during the day and 40°F at night. Cap off your sightseeing on the 30th (Tue) early enough to catch the flight back home.
Museums · Breweries & Distilleries · Parks · Historic Sites
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.