30 days in Maryland Itinerary

30 days in Maryland Itinerary

Created using Inspirock Maryland trip planner

Make it your trip
Fly
1
St. Michaels
— 5 nights
Drive
2
Ocean City
— 7 nights
Drive
3
Cumberland
— 5 nights
Drive
4
Sharpsburg
— 3 nights
Drive
5
Baltimore
— 9 nights
Train

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St. Michaels

— 5 nights
You'll find plenty of places to visit near St. Michaels: Layton's Chance Vineyard and Winery (in Vienna), Cambridge (Blackwater National Wildlife Refuge & Harriet Tubman Museum and Educational Center) and Blackwater Distilling & Tavern (in Stevensville).

For more things to do, where to stay, and other tourist information, you can read our St. Michaels trip planner.

New York City to St. Michaels is an approximately 3-hour flight. You can also drive; or do a combination of train, bus, and taxi. Expect a daytime high around 58°F in November, and nighttime lows around 40°F. Wrap up your sightseeing on the 6th (Sat) to allow time to drive to Ocean City.

Things to do in St. Michaels

Museums · Historic Sites · Breweries & Distilleries · Parks

Side Trips

Ocean City

— 7 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.
Explore Ocean City's surroundings by going to Salisbury (Ward Museum of Wildfowl Art & Eastern Shore Baseball Hall of Fame Museum), Crisfield Heritage Foundation (in Crisfield) and Bishop's Stock Fine Art, Craft & Wine (in Snow Hill). There's still lots to do: walk around Northside Park, see what you can catch with a fishing tour, get outside with Ayers Creek Adventures, and admire the majestic nature at Assateague State Park.

For photos, where to stay, ratings, and other tourist information, read Ocean City road trip planning website.

Getting from St. Michaels to Ocean City by car takes about 2 hours. Other options: do a combination of taxi and shuttle; or do a combination of taxi and bus. Expect a daytime high around 57°F in November, and nighttime lows around 39°F. Finish your sightseeing early on the 13th (Sat) so you can travel to Cumberland.

Things to do in Ocean City

Outdoors · Museums · Parks · Wildlife

Side Trips

Cumberland

— 5 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: C&O Canal Trust (in Hagerstown), FireFly Farms Market (in Accident) and The Discovery Center (in Swanton). Next up on the itinerary: grab your bike and head to Great Allegheny Passage, steep yourself in history at Gordon-Roberts House, don't miss a visit to Allegany Fairgrounds, and immerse yourself in nature at New Germany State Park.

To find other places to visit, reviews, photos, and tourist information, use the Cumberland sightseeing planning app.

Traveling by car from Ocean City to Cumberland takes 4.5 hours. Alternatively, you can do a combination of car and flight. Traveling from Ocean City in November, expect a bit cooler with lows of 34°F in Cumberland. Finish your sightseeing early on the 18th (Thu) to allow enough time to drive to Sharpsburg.

Things to do in Cumberland

Parks · Nature · Historic Sites · Outdoors

Side Trips

Sharpsburg

— 3 nights
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Change things up with a short trip to Lockhouse 49 in Clear Spring (about 32 minutes away). There's lots more to do: contemplate the long history of Tolson's Chapel, witness the site of a historic battle at Antietam National Battlefield, relax in the rural setting at Frog Eye Farm, and get engrossed in the history at Washington County Rural Heritage Museum.

To find maps, photos, other places to visit, and other tourist information, refer to the Sharpsburg trip planner.

You can drive from Cumberland to Sharpsburg in 1.5 hours. Expect a daytime high around 56°F in November, and nighttime lows around 34°F. Wrap up your sightseeing on the 21st (Sun) early enough to drive to Baltimore.

Things to do in Sharpsburg

Historic Sites · Parks · Nature · Museums

Side Trips

Baltimore

— 9 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.
You'll find plenty of places to visit near Baltimore: Annapolis (Annapolis Historic District & U.S. Naval Academy), Meadowside Nature Center (in Rockville) and The Adventure Park at Sandy Spring (in Sandy Spring). Spend the 30th (Tue) exploring nature at Fort McHenry National Monument and Historic Shrine. And it doesn't end there: try your luck at Horseshoe Casino, explore the world behind art at The Walters Art Museum, see the interesting displays at American Visionary Art Museum, and get up close and personal with brilliant marine life at National Aquarium.

To find ratings, maps, photos, and other tourist information, go to the Baltimore travel route builder app.

You can drive from Sharpsburg to Baltimore in 1.5 hours. Traveling from Sharpsburg in November, plan for a bit warmer nights in Baltimore, with lows around 43°F. Finish your sightseeing early on the 30th (Tue) to allow enough time to take a train back home.

Things to do in Baltimore

Parks · Museums · Historic Sites · 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.