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). The adventure continues: immerse yourself in nature at Swallow Falls State Park, contemplate the waterfront views at Deep Creek Lake State Park, tee off at Lodestone Golf Course, and walk around Herrington Manor State Park.

To see ratings, where to stay, photos, and more tourist information, go to the Oakland trip planner.

Atlanta to Oakland is an approximately 6.5-hour combination of flight and car. You can also drive. Expect slightly colder temperatures when traveling from Atlanta in May; daily highs in Oakland reach 63°F and lows reach 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: Renfrew Museum and Park (in Waynesboro), Mount Airy (Loew vinyards & Black Ankle Vineyards) and Penn National Golf Course (in Fayetteville). 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 take in the views from Roddy Road Covered Bridge.

To find other places to visit, ratings, and tourist information, read our Emmitsburg online journey builder.

Traveling by car from Oakland to Emmitsburg takes 3 hours. Prepare for somewhat warmer weather when traveling from Oakland in May: high temperatures in Emmitsburg hover around 71°F and lows are around 53°F. Wrap up your sightseeing on the 10th (Mon) early enough 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 nature. Your trip includes some of its best attractions: walk around Watkins Regional Park, do a tasting at Robin Hill Farm and Vineyards, take an in-depth tour of Surratt House Museum, and tour the pleasant surroundings at Jug Bay Wetlands Sanctuary.

For ratings, reviews, more things to do, and more tourist information, read our Upper Marlboro day trip site.

You can drive from Sandy Spring to Upper Marlboro in an hour. In May, daytime highs in Upper Marlboro are 73°F, while nighttime lows are 55°F. Wrap up your sightseeing on the 16th (Sun) early enough to drive to Annapolis.

Things to do in Upper Marlboro

Parks · Nature · Wildlife · 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: Six Flags America (in Bowie), Historical Society of Kent County (in Chestertown) 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 identify plant and animal life 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: Salisbury (Ben's Red Swings Community Playground, Salisbury Zoo, &more), Layton's Chance Vineyard and Winery (in Vienna) and Blackwater National Wildlife Refuge (in Cambridge). Next up on the itinerary: see the interesting displays at Chesapeake Bay Maritime Museum, sample the tasty concoctions at Eastern Shore Brewing, admire the masterpieces at Academy Art Museum, and learn about winemaking at Saint Michaels Winery.

For more things to do, other places to visit, maps, and tourist information, read Easton road trip website.

Getting from Stevensville to Easton by car takes about an hour. Expect a daytime high around 75°F in May, and nighttime lows around 57°F. Wrap up your sightseeing on the 2nd (Wed) early enough to travel to Assateague Island.

Things to do in Easton

Museums · Parks · Historic Sites · Fun & Games

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

Nature · Parks · Wildlife
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: Menokin (in Warsaw), Leonardtown (Leonardtown Wharf Park, Port of Leonardtown Winery, &more) and Hague (General's Ridge Vineyard and Winery & The Hague Winery). Next up on the itinerary: don't miss a visit to Historic St. Mary's City, steep yourself in history at The Dr. Samuel Mudd House & Museum, learn about winemaking at Good Luck Cellars, and go for a stroll along the water at Bayside Marina.

To see other places to visit, ratings, and tourist information, read our Prince Frederick trip planner.

Explore your travel options from Assateague Island to Prince Frederick with the Route module. June in Prince Frederick sees daily highs of 81°F and lows of 64°F at night. Finish up your sightseeing early on the 10th (Thu) so you can travel back home.

Things to do in Prince Frederick

Wineries · Historic Sites · Parks · Museums

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.

Montgomery County travel guide

4.5
Theme Parks · Theaters · Parks