41 days in Maryland Itinerary

41 days in Maryland Itinerary

Created using Inspirock Maryland vacation builder

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Make it your trip
Fly to Washington Dulles International Airport, Drive to Oakland
1
Oakland
— 3 nights
Drive
2
Emmitsburg
— 6 nights
Drive
3
Sandy Spring
— 2 nights
Drive
4
Upper Marlboro
— 4 nights
Drive
5
Annapolis
— 9 nights
Drive
6
Stevensville
— 2 nights
Drive
7
Easton
— 6 nights
Unknown
8
Assateague Island
— 1 night
Unknown
9
Prince Frederick
— 7 nights
Drive to Ronald Reagan Washington National Airport, Fly to Atlanta

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Oakland

— 3 nights
Oakland is a town in the west-central part of Garrett County, Maryland. You'll find plenty of places to visit near Oakland: Grantsville (Spruce Forest Artisan Village & New Germany State Park). There's lots more to do: admire the majestic nature at Swallow Falls State Park, contemplate the waterfront views at Deep Creek Lake State Park, play a few rounds at Lodestone Golf Course, and take an in-depth tour of The Oakland B&O Railroad Museum.

To find traveler tips, more things to do, and tourist information, go to the Oakland trip builder site.

Atlanta to Oakland is an approximately 6.5-hour combination of flight and car. You can also drive. Traveling from Atlanta in May, things will get slightly colder in Oakland: highs are around 63°F and lows about 47°F. Wrap up your sightseeing on the 4th (Tue) to allow time to travel to Emmitsburg.

Things to do in Oakland

Parks · Nature · Outdoors · Museums

Side Trips

Emmitsburg

— 6 nights
Emmitsburg is a town in Frederick County, Maryland, United States, just south of the Mason-Dixon line separating Maryland from Pennsylvania. You'll find plenty of places to visit near Emmitsburg: Mount Airy (Loew vinyards & Black Ankle Vineyards), Penn National Golf Course (in Fayetteville) and Renfrew Museum and Park (in Waynesboro). The adventure continues: take in the spiritual surroundings of National Shrine of St. Elizabeth Ann Seton, do a tasting at Red Heifer Winery, pause for some photo ops at National Fallen Firefighters Memorial, and enjoy the scholastic atmosphere at Mount St. Mary's University and Seminary.

To find maps, where to stay, traveler tips, and more tourist information, you can read our Emmitsburg day trip tool.

Traveling by car from Oakland to Emmitsburg takes 3 hours. In May, Emmitsburg is somewhat warmer than Oakland - with highs of 71°F and lows of 53°F. Finish your sightseeing early on the 10th (Mon) to allow enough time to travel to Sandy Spring.

Things to do in Emmitsburg

Parks · Outdoors · Wineries · Nature

Side Trips

Sandy Spring

— 2 nights
Sandy Spring, Maryland is an unincorporated community in Montgomery County, Maryland.GeographySandy Spring's boundaries are roughly Brooke Road and Dr. On the 11th (Tue), take in nature's colorful creations at Brookside Nature Center, then admire the natural beauty at Brookside Gardens, and then learn about winemaking at The Winery at Olney. Get ready for a full day of sightseeing on the 12th (Wed): get in on the family fun at The Adventure Park at Sandy Spring.

To find photos, ratings, where to stay, and other tourist information, use the Sandy Spring trip itinerary planning app.

Drive from Emmitsburg to Sandy Spring in 1.5 hours. In May, daily temperatures in Sandy Spring can reach 71°F, while at night they dip to 52°F. Cap off your sightseeing on the 12th (Wed) early enough to travel to Upper Marlboro.

Things to do in Sandy Spring

Theme Parks · Parks · Wineries

Side Trips

Upper Marlboro

— 4 nights
Upper Marlboro, officially the Town of Upper Marlboro, is the seat of Prince George's County, Maryland in the United States. Upper Marlboro is known for parks, shopping, and wildlife. Your plan includes some of its best attractions: walk around Watkins Regional Park, look for all kinds of wild species at Merkle Wildlife Sanctuary, immerse yourself in nature at Patuxent River Park, and do a tasting at Robin Hill Farm and Vineyards.

To find photos, other places to visit, where to stay, and other tourist information, refer to the Upper Marlboro road trip site.

Traveling by car from Sandy Spring to Upper Marlboro takes an hour. In May in Upper Marlboro, expect temperatures between 73°F during the day and 55°F at night. Wrap up your sightseeing on the 16th (Sun) early enough to drive to Annapolis.

Things to do in Upper Marlboro

Parks · Wildlife · Nature · Wineries

Side Trips

Annapolis

— 9 nights
Capital of the United States for one year from 1783 to 1784, Annapolis has played a vital role in U.S. history.
You'll find plenty of places to visit near Annapolis: Historical Society of Kent County (in Chestertown), Six Flags America (in Bowie) and Dover (Air Mobility Command Museum, John Dickinson Plantation, &more). The adventure continues: explore the galleries of U.S. Naval Academy, wander the streets of Annapolis Historic District, contemplate the long history of Hammond-Harwood House, and trek along Quiet Waters Park.

For more things to do, traveler tips, ratings, and more tourist information, use the Annapolis road trip planner.

You can drive from Upper Marlboro to Annapolis in an hour. In May, daytime highs in Annapolis are 72°F, while nighttime lows are 58°F. Wrap up your sightseeing on the 25th (Tue) early enough to drive to Stevensville.

Things to do in Annapolis

Historic Sites · Parks · Outdoors · Neighborhoods

Side Trips

Stevensville

— 2 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. Start off your visit on the 26th (Wed): head outdoors with Lead Dog Charters, then grab your bike and head to Chesapeake Heritage & Visitors Center, then tour the pleasant surroundings at Terrapin Nature Park, and finally brush up on your knowledge of spirits at Blackwater Distilling & Tavern. On the 27th (Thu), you'll have a packed day of sightseeing: kick back and relax at Matapeake Clubhouse and Beach, get outside with Casey Michelle Charters, and then take a tour by water with Chesapeake Bay Charter Services.

To find reviews, maps, ratings, and other tourist information, read our Stevensville trip itinerary planning site.

Stevensville is just a stone's throw from Annapolis. In May, daily temperatures in Stevensville can reach 72°F, while at night they dip to 56°F. Finish up your sightseeing early on the 27th (Thu) so you can go by car to Easton.

Things to do in Stevensville

Outdoors · Wildlife · Parks · Trails

Side Trip

Easton

— 6 nights
Easton, Maryland is an incorporated town and the county seat of Talbot County, Maryland, United States. You'll find plenty of places to visit near Easton: Layton's Chance Vineyard and Winery (in Vienna), Blackwater National Wildlife Refuge (in Cambridge) and Salisbury (Ben's Red Swings Community Playground, Salisbury Zoo, &more). And it doesn't end there: get a new perspective on things with Boat Tours & Water Sports, contemplate the long history of The Third Haven Friends Meeting House, indulge your thirst for a good beer at Eastern Shore Brewing, and do a tasting at Saint Michaels Winery.

To see other places to visit, photos, and other tourist information, you can read our Easton trip planning site.

Drive from Stevensville to Easton in an hour. In May in Easton, expect temperatures between 75°F during the day and 57°F at night. Cap off your sightseeing on the 2nd (Wed) early enough to travel to Assateague Island.

Things to do in Easton

Museums · Parks · Fun & Games · Historic Sites

Side Trips

Assateague Island

— 1 night
Kick off your visit on the 3rd (Thu): explore the wealth of natural beauty at Assateague Island National Seashore.

For more things to do, other places to visit, traveler tips, and other tourist information, read Assateague Island trip maker website.

Explore your travel options from Easton to Assateague Island with the Route module. Expect little chillier weather when traveling from Easton in June: highs in Assateague Island hover around 79°F, while lows dip to 65°F. Finish up your sightseeing early on the 3rd (Thu) so you can travel to Prince Frederick.

Things to do in Assateague Island

Wildlife · Nature · Parks
Highlights from your trip

Prince Frederick

— 7 nights
Prince Frederick is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. Explore the numerous day-trip ideas around Prince Frederick: Hague (General's Ridge Vineyard and Winery & The Hague Winery), Menokin (in Warsaw) and Leonardtown (Leonardtown Wharf Park, Port of Leonardtown Winery, &more). The adventure continues: admire the landmark architecture of Historic Christ Church, immerse yourself in nature at Westmoreland State Park, explore the galleries of Historic St. Mary's City, and learn about winemaking at Slack Winery.

To find photos, other places to visit, traveler tips, and tourist information, read Prince Frederick visit planner.

The Route module can help you plan travel from Assateague Island to Prince Frederick. June in Prince Frederick sees daily highs of 81°F and lows of 64°F at night. Wrap up your sightseeing on the 10th (Thu) to allow time to travel back home.

Things to do in Prince Frederick

Wineries · Historic Sites · Parks · Museums

Side Trips

Maryland travel guide

4.1
Casinos · Aquariums · Specialty Museums
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.

Montgomery County travel guide

4.5
Theaters · Theme Parks · Parks