30 days in Maryland Itinerary

30 days in Maryland Itinerary

Created using Inspirock Maryland route planner
Make it your trip
Fly
1
St. Michaels
— 5 nights
Drive
2
Ocean City
— 6 nights
Drive
3
Cumberland
— 5 nights
Drive
4
Hagerstown
— 5 nights
Drive
5
Baltimore
— 8 nights
Train

S M T W T F S
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4

St. Michaels — 5 nights

Explore St. Michaels' surroundings by going to Blackwater Distilling & Tavern (in Stevensville), Cambridge (Blackwater National Wildlife Refuge & Harriet Tubman Museum and Educational Center) and Eastern Neck National Wildlife Refuge (in Rock Hall).

To find where to stay, other places to visit, ratings, and other tourist information, read St. Michaels online 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. In November in St. Michaels, expect temperatures between 58°F during the day and 40°F at night. Finish up your sightseeing early on the 6th (Sat) so you can go by car to Ocean City.
Museums · Parks · Breweries & Distilleries · Wildlife
Side Trips

Ocean City — 6 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: Bishop's Stock Fine Art, Craft & Wine (in Snow Hill) and Salisbury (Eastern Shore Baseball Hall of Fame Museum & Ward Museum of Wildfowl Art). There's still lots to do: stroll around Northside Park, take a tour by water with Boat Tours & Water Sports, admire the majestic nature at Assateague State Park, and indulge your thirst for a good beer at Burley Oak Brewing Company.

To see reviews, where to stay, ratings, and more tourist information, you can read our Ocean City trip planner.

You can drive from St. Michaels to Ocean City in 2 hours. Other options are to do a combination of taxi and shuttle; or do a combination of taxi and bus. In November in Ocean City, expect temperatures between 57°F during the day and 39°F at night. Finish your sightseeing early on the 12th (Fri) so you can travel to Cumberland.
Outdoors · Parks · Museums · 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: Garrett County Historical Museum (in Oakland), New Germany State Park (in Grantsville) and The Discovery Center (in Swanton). And it doesn't end there: grab your bike and head to Great Allegheny Passage, contemplate the long history of Paw Paw Tunnel, sample the fine beverages at Charis Winery & Distillery, and immerse yourself in nature at Casselman River Bridge State Park.

To find reviews, other places to visit, more things to do, and other tourist information, read Cumberland online holiday planner.

You can drive from Ocean City to Cumberland in 4.5 hours. Alternatively, you can do a combination of car and flight. Traveling from Ocean City in November, you can expect nighttime temperatures to be slightly colder in Cumberland, with lows of 34°F. Finish your sightseeing early on the 17th (Wed) to allow enough time to drive to Hagerstown.
Parks · Nature · Museums · Trails
Side Trips

Hagerstown — 5 nights

Hagerstown is a city in Washington County, Maryland, United States. Change things up with these side-trips from Hagerstown: Catoctin Mountain Park (in Thurmont), Emmitsburg (National Shrine of St. Elizabeth Ann Seton & National Shrine Grotto of Lourdes) and Frederick (Monocacy National Battlefield, Historic Downtown Frederick, &more). The adventure continues: explore the activities along C&O Canal Trust, make a trip to Lockhouse 49, and contemplate the long history of Tolson's Chapel.

To see other places to visit, where to stay, and more tourist information, read Hagerstown itinerary builder site.

Drive from Cumberland to Hagerstown in 1.5 hours. November in Hagerstown sees daily highs of 54°F and lows of 37°F at night. Cap off your sightseeing on the 22nd (Mon) early enough to go by car to Baltimore.
Historic Sites · Parks · Nature · Museums
Side Trips

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.
Explore Baltimore's surroundings by going to Magdalen's Pure Skin Care Day Spa (in Rockville), Annapolis (Annapolis Historic District & U.S. Naval Academy) and Fishpaws Marketplace (in Arnold). Spend the 30th (Tue) exploring nature at Fort McHenry National Monument and Historic Shrine. There's still lots to do: try your luck at Horseshoe Casino, explore the world behind art at The Walters Art Museum, wander the streets of Fell's Point, and see the interesting displays at American Visionary Art Museum.

To find ratings, more things to do, photos, and more tourist information, go to the Baltimore holiday maker website.

Traveling by car from Hagerstown to Baltimore takes 1.5 hours. Expect somewhat warmer evenings in Baltimore when traveling from Hagerstown in November, with lows around 43°F. Finish up your sightseeing early on the 30th (Tue) so you can catch the train back home.
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.