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 Baltimore Museum of Art and The Baltimore Basilica. 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 still lots to do: contemplate the long history of B&O Railroad Museum, engage your brain at Maryland Science Center, enjoy breathtaking views from Top of the World Observation Level, and brush up on your knowledge of spirits at Sagamore Spirit Distillery.

To see reviews, other places to visit, more things to do, and other tourist information, use the Baltimore holiday planning app.

New York City to Baltimore is an approximately 3-hour train ride. You can also drive; or take a bus. In November, daily temperatures in Baltimore can reach 57°F, while at night they dip to 43°F. Finish your sightseeing early on the 5th (Fri) so you can drive to Cumberland.
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Parks · Historic Sites · Museums · 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 Great Allegheny Passage. Get out of town with these interesting Cumberland side-trips: Wisp Resort (in McHenry), FireFly Farms Market (in Accident) and Oakland (Deep Creek Lake State Park & Swallow Falls State Park). There's lots more to do: don't miss a visit to Sideling Hill Welcome Center, contemplate the long history of Spruce Forest Artisan Village, try to win big at Rocky Gap Casino Resort, and tee off at Rocky Gap Golf Course.

To find ratings, traveler tips, maps, and tourist information, use the Cumberland day trip site.

You can drive from Baltimore to Cumberland in 2.5 hours. Traveling from Baltimore in November, plan for slightly colder nights in Cumberland, with lows around 34°F. Finish your sightseeing early on the 9th (Tue) so you can drive to Hagerstown.
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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 C&O Canal Trust and Pennsylvania Dutch Market. Explore Hagerstown's surroundings by going to Emmitsburg (National Shrine Grotto of Lourdes & National Shrine of St. Elizabeth Ann Seton), Catoctin Mountain Park (in Thurmont) and Frederick (Weinberg Center for the Arts, Historic Downtown Frederick, &more). There's more to do: stroll the grounds of Antietam National Cemetery and admire the majestic nature at Greenbrier State Park.

Before you visit Hagerstown, use our trip planner to discover what you can do and see there.

Traveling by car from Cumberland to Hagerstown takes 1.5 hours. Alternatively, you can drive. In November, daytime highs in Hagerstown are 54°F, while nighttime lows are 37°F. Finish your sightseeing early on the 13th (Sat) so you can drive to Solomons.
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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: pick up some new knowledge with Annmarie Garden, take an in-depth tour of Historic St. Mary's City, brush up on your military savvy at Patuxent River Naval Air Museum, and trek along Flag Ponds Nature Park.

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. Alternatively, you can drive. 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.
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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, tour the pleasant surroundings 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.
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Parks · Outdoors · Beaches · Trails

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 Spas. Change things up with these side-trips from Cambridge: Boat Tours & Water Sports (in Tilghman) and St. Michaels (Saint Michaels Winery, 1879 Hooper Strait Lighthouse, &more). The adventure continues: take an in-depth tour of Harriet Tubman Museum and Educational Center, examine the collection at The Oxford Museum, get answers to all your questions at Harriet Tubman Underground Railroad National Historical Park, and take in the architecture and atmosphere at Christ Episcopal Church.

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.
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Museums · Historic Sites · Breweries & Distilleries · Spas
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 Assateague State Park. Explore the numerous day-trip ideas around Ocean City: Manokin River Park (in Princess Anne) and Salisbury (The Centre at Salisbury, Ward Museum of Wildfowl Art, &more). There's still lots to do: cast your line with a fishing tour, stroll around Ocean Bowl Skate Park, tee off at Rum Pointe Seaside Golf Links, and get in on the family fun at Trimper Rides and Amusement Park.

For other places to visit, where to stay, traveler tips, and other tourist information, refer to the Ocean City trip app.

Traveling by car from Cambridge to Ocean City takes 1.5 hours. In November, daytime highs in Ocean City are 57°F, while nighttime lows are 39°F. Finish your sightseeing early on the 30th (Tue) so you can drive back home.
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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.
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