40 days in Maryland Itinerary

40 days in Maryland Itinerary

Created using Inspirock Maryland travel route builder
Make it your trip
Fly to Washington Dulles International Airport, Drive to Oakland
1
Oakland
— 4 nights
Drive
2
Emmitsburg
— 2 nights
Drive
3
Baltimore
— 16 nights
Drive
4
Stevensville, Kent Island
— 3 nights
Unknown
5
Assateague Island
— 2 nights
Unknown
6
Ocean City
— 6 nights
Drive
7
St. Michaels
— 5 nights
Drive to Baltimore/Washington International Thurgood Marshall Airport, Fly to Nairobi

S M T W T F S
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
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
1
2
3
4
5

Oakland — 4 nights

Oakland is a town in the west-central part of Garrett County, Maryland. Venture out of the city with trips to Cumberland (Great Allegheny Passage & Charis Winery & Distillery). The adventure continues: see the interesting displays at Garrett County Museum of Transportation, look for gifts at Schoolhouse Earth, tour the pleasant surroundings at Wisp Resort, and immerse yourself in nature at Swallow Falls State Park.

To find ratings, reviews, maps, and other tourist information, read our Oakland trip planning app.

Nairobi, Kenya to Oakland is an approximately 23-hour combination of flight and car. The time zone difference when traveling from Nairobi to Oakland is minus 8 hours. Traveling from Nairobi in January, expect Oakland to be cooler, temps between 0°C and -9°C. Finish your sightseeing early on the 24th (Mon) to allow enough time to travel to Emmitsburg.
Museums · Parks · Outdoors · Breweries & Distilleries
Side Trips

Emmitsburg — 2 nights

Emmitsburg is a town in Frederick County, Maryland, United States, just south of the Mason-Dixon line separating Maryland from Pennsylvania. Start off your visit on the 25th (Tue): contemplate in the serene atmosphere at National Shrine of St. Elizabeth Ann Seton and then pause for some photo ops at National Shrine Grotto of Lourdes. Here are some ideas for day two: pause for some photo ops at Our Lady of the Mountain and then walk around Penn Mar Park.

Plan a Emmitsburg trip in moments using our itinerary builder.

You can drive from Oakland to Emmitsburg in 3 hours. Plan for a bit warmer nights when traveling from Oakland in January since evenings lows in Emmitsburg dip to -5°C. Finish up your sightseeing early on the 26th (Wed) so you can go by car to Baltimore.
Museums · Historic Sites · Parks
Side Trip

Baltimore — 16 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 the numerous day-trip ideas around Baltimore: Magdalen's Pure Skin Care Day Spa (in Rockville), Fishpaws Marketplace (in Arnold) and RIO Washingtonian Center (in Gaithersburg). Spend the 30th (Sun) exploring nature at Fort McHenry National Monument and Historic Shrine. There's still lots to do: try your luck at Horseshoe Casino, see the interesting displays at Jewish Museum of Maryland, stroll through Federal Hill Park, and learn the secrets of beer at City Brew Tours Baltmore.

To see other places to visit, ratings, reviews, and more tourist information, read our Baltimore trip planner.

Traveling by car from Emmitsburg to Baltimore takes 1.5 hours. In January, plan for daily highs up to 6°C, and evening lows to -1°C. Wrap up your sightseeing on the 11th (Fri) to allow time to drive to Stevensville.
Museums · Historic Sites · Parks · Breweries & Distilleries
Side Trips

Stevensville, Kent Island — 3 nights

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. Step out of Stevensville with an excursion to Jefferson Patterson Park & Museum in Saint Leonard--about 1h 15 min away. And it doesn't end there: brush up on your knowledge of spirits at Blackwater Distilling & Tavern, head outdoors with Casey Michelle Charters, browse the fresh offerings at Diehl's Produce Market, and get answers to all your questions at Chesapeake Heritage & Visitors Center.

For where to stay, reviews, and other tourist information, use the Stevensville online route maker.

Getting from Baltimore to Stevensville by car takes about an hour. In February, plan for daily highs up to 7°C, and evening lows to 0°C. Finish your sightseeing early on the 14th (Mon) so you can travel to Assateague Island.
Outdoors · Parks · Breweries & Distilleries · Museums
Side Trips

Assateague Island — 2 nights

Kick off your visit on the 15th (Tue): stroll through Assateague Island National Seashore.

To see other places to visit, photos, ratings, and tourist information, read our Assateague Island trip itinerary builder tool.

The Route module can help you plan travel from Stevensville to Assateague Island. February in Assateague Island sees daily highs of 8°C and lows of -1°C at night. You'll set off for Ocean City on the 16th (Wed).
Wildlife · Parks · Nature
Highlights from your trip

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.
Get out of town with these interesting Ocean City side-trips: Crisfield Heritage Foundation (in Crisfield) and Salisbury (Ward Museum of Wildfowl Art, Salisbury Zoo, &more). There's lots more to do: stroll around Northside Park, kick back and relax at Ocean City Beach, view the masterpieces at Art League of Ocean City, and take in the waterfront at Ocean City Boardwalk.

To see ratings, reviews, where to stay, and other tourist information, you can read our Ocean City travel route site.

Use the Route module to find suitable travel options from Assateague Island to Ocean City. Expect a daytime high around 8°C in February, and nighttime lows around -1°C. Finish your sightseeing early on the 22nd (Tue) to allow enough time to drive to St. Michaels.
Parks · Museums · Outdoors · Tours
Side Trips

St. Michaels — 5 nights

You'll find plenty of places to visit near St. Michaels: Historical Society of Kent County (in Chestertown), Outstanding Dreams Farm (in Preston) and Cambridge (Bay Country Shop, Blackwater National Wildlife Refuge, &more).

For traveler tips, maps, and more tourist information, you can read our St. Michaels vacation planning website.

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 February, daytime highs in St. Michaels are 9°C, while nighttime lows are -1°C. Finish your sightseeing early on the 27th (Sun) so you can travel back home.
Museums · Shopping · Breweries & Distilleries · Wildlife
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.