30 days in Maryland Itinerary

30 days in Maryland Itinerary

Created using Inspirock Maryland trip planner

Make it your trip
Train
1
Baltimore
— 4 nights
Drive
2
Cumberland
— 4 nights
Drive
3
Hagerstown
— 4 nights
Drive
4
Solomons
— 3 nights
Drive
5
Stevensville, Kent Island
— 1 night
Drive
6
Cambridge
— 4 nights
Drive
7
Ocean City
— 9 nights
Drive

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Baltimore

— 4 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 discover tucked-away gems like B&O Railroad Museum and Baltimore Museum of Art. Explore the numerous day-trip ideas around Baltimore: Annapolis (Maryland State House, Quiet Waters Park, &more), Conowingo Dam (in Darlington) and Havre de Grace (Susquehanna State Park & Havre de Grace Promenade). There's much more to do: contemplate in the serene atmosphere at The Baltimore Basilica, sample the tasty concoctions at Guinness Open Gate Brewery & Barrel House, take in panoramic vistas at Top of the World Observation Level, and get curious at Maryland Science Center.

To see traveler tips, more things to do, ratings, and tourist information, use the Baltimore day trip app.

New York City to Baltimore is an approximately 3-hour train ride. You can also drive; or take a bus. In November in Baltimore, expect temperatures between 57°F during the day and 43°F at night. Finish up your sightseeing early on the 5th (Fri) so you can go by car to Cumberland.

Things to do in Baltimore

Parks · Museums · Historic Sites · Nature

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. You'll discover tucked-away gems like Paw Paw Tunnel and Sideling Hill Welcome Center. Get out of town with these interesting Cumberland side-trips: Oakland (Deep Creek Lake State Park & Swallow Falls State Park), Wisp Resort (in McHenry) and FireFly Farms Market (in Accident). Next up on the itinerary: contemplate the long history of George Washington's Headquarters, make a trip to National Road & Toll House, play a few rounds at Rocky Gap Golf Course, and try your luck at Rocky Gap Casino Resort.

For photos, traveler tips, other places to visit, and other tourist information, read our Cumberland trip itinerary builder.

Traveling by car from Baltimore to Cumberland takes 2.5 hours. Traveling from Baltimore in November, Cumberland is a bit cooler at night with lows of 34°F. Finish your sightseeing early on the 9th (Tue) so you can drive to Hagerstown.

Things to do in Cumberland

Parks · Outdoors · Nature · Historic Sites

Side Trips

Hagerstown

— 4 nights
Hagerstown is a city in Washington County, Maryland, United States. Discover out-of-the-way places like National Museum of Civil War Medicine and Pennsylvania Dutch Market. Explore Hagerstown's surroundings by going to Frederick (Weinberg Center for the Arts, Historic Downtown Frederick, &more) and Emmitsburg (National Shrine Grotto of Lourdes & National Shrine of St. Elizabeth Ann Seton). And it doesn't end there: contemplate the waterfront views at C&O Canal Trust, immerse yourself in nature at Catoctin Mountain Park, and explore the different monuments and memorials at Antietam National Cemetery.

To see other places to visit, photos, maps, and other tourist information, read our Hagerstown road trip planning tool.

You can drive from Cumberland to Hagerstown in 1.5 hours. In November, daily temperatures in Hagerstown can reach 54°F, while at night they dip to 37°F. Finish your sightseeing early on the 13th (Sat) so you can travel to Solomons.

Things to do in Hagerstown

Parks · Historic Sites · Museums · Nature

Side Trips

Solomons

— 3 nights
Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. You'll discover tucked-away gems like Calvert Marine Museum and Drum Point Lighthouse and Solomons Boat Ramp and Fishing Pier. Venture out of the city with trips to Janes Island State Park (in Crisfield) and St. George Island (in Piney Point). Next up on the itinerary: view the masterpieces at Annmarie Garden, learn about all things military at Patuxent River Naval Air Museum, hike along Flag Ponds Nature Park, and take an in-depth tour of Historic St. Mary's City.

To find reviews, ratings, traveler tips, and other tourist information, go to the Solomons road trip planning tool.

Traveling by car from Hagerstown to Solomons takes 2.5 hours. Expect a daytime high around 58°F in November, and nighttime lows around 40°F. Cap off your sightseeing on the 16th (Tue) early enough to go by car to Stevensville.

Things to do in Solomons

Parks · Museums · Nature · Outdoors

Side Trips

Stevensville, Kent Island

— 1 night
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 17th (Wed): tour the pleasant surroundings at Matapeake Clubhouse and Beach, explore and take pictures at Terrapin Nature Park, and then brush up on your knowledge of spirits at Blackwater Distilling & Tavern.

To find more things to do, photos, maps, and tourist information, you can read our Stevensville trip itinerary app.

Traveling by car from Solomons to Stevensville takes 2 hours. November in Stevensville sees daily highs of 55°F and lows of 41°F at night. Wrap up your sightseeing on the 17th (Wed) early enough to drive to Cambridge.

Things to do in Stevensville

Parks · Outdoors · Trails · Wildlife

Cambridge

— 4 nights
Cambridge is a city in Dorchester County, Maryland, United States. Step off the beaten path and head to Blackwater National Wildlife Refuge and Harriet Tubman Museum and Educational Center. Change things up with these side-trips from Cambridge: St. Michaels (Saint Michaels Winery, 1879 Hooper Strait Lighthouse, &more) and Boat Tours & Water Sports (in Tilghman). The adventure continues: pause for some serene contemplation at Christ Episcopal Church, get engrossed in the history at Harriet Tubman Underground Railroad National Historical Park, see the interesting displays at The Oxford Museum, and stop by The Amish Market.

To find maps, reviews, ratings, and other tourist information, refer to the Cambridge trip itinerary maker site.

Traveling by car from Stevensville to Cambridge takes an hour. In November, daily temperatures in Cambridge can reach 57°F, while at night they dip to 39°F. Cap off your sightseeing on the 21st (Sun) early enough to go by car to Ocean City.

Things to do in Cambridge

Museums · Historic Sites · Breweries & Distilleries · Outdoors

Side Trips

Ocean City

— 9 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.
You'll discover tucked-away gems like Northside Park and Ocean Bowl Skate Park. Explore the numerous day-trip ideas around Ocean City: Salisbury (The Centre at Salisbury, Ward Museum of Wildfowl Art, &more) and Manokin River Park (in Princess Anne). There's lots more to do: see what you can catch with a fishing tour, make a splash at Frontier Town, get in on the family fun at Trimper's Rides and Amusement Park, and immerse yourself in nature at Assateague State Park.

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

Getting from Cambridge to Ocean City by car takes about 1.5 hours. In November in Ocean City, expect temperatures between 57°F during the day and 39°F at night. Finish up your sightseeing early on the 30th (Tue) so you can go by car back home.

Things to do in Ocean City

Outdoors · Parks · Shopping · Golf

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.