41 days in Maryland Itinerary

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, examine the collection at Garrett County Museum of Transportation, tee off at Lodestone Golf Course, and take an in-depth tour of The Oakland B&O Railroad Museum.

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

Atlanta to Oakland is an approximately 7-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 drive to Emmitsburg.

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), Renfrew Museum and Park (in Waynesboro) and Penn National Golf Course (in Fayetteville). The adventure continues: take in the spiritual surroundings of National Shrine of St. Elizabeth Ann Seton, pause for some photo ops at Our Lady of the Mountain, take in the views from Loy's Station Covered Bridge, and walk around Penn Mar Park.

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

The Route module can help you plan travel from Oakland to Emmitsburg. 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 drive to Sandy Spring.

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.

Explore your travel options from Emmitsburg to Sandy Spring with the Route module. 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 go by car to Upper Marlboro.

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 trip includes some of its best attractions: walk around Watkins Regional Park, look for all kinds of wild species at Jug Bay Wetlands Sanctuary, admire the majestic nature at Patuxent River Park, and shop like a local with Dutch Village Farmers Market.

To find traveler tips, ratings, reviews, and more tourist information, read our Upper Marlboro tour planner.

Use the Route module to find suitable travel options from Sandy Spring to Upper Marlboro. In May, daily temperatures in Upper Marlboro can reach 73°F, while at night they dip to 55°F. Finish your sightseeing early on the 16th (Sun) to allow enough time to drive to Annapolis.

Capital of the United States for one year from 1783 to 1784, Annapolis has played a vital role in U.S. history.

Explore Annapolis' surroundings by going to Historical Society of Kent County (in Chestertown), Dover (Air Mobility Command Museum, John Dickinson Plantation, &more) and Six Flags America (in Bowie). The adventure continues: expand your understanding of the military at U.S. Naval Academy, indulge your thirst for a good beer at Dogfish Head Craft Brewery, 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.

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): cast your line with Lead Dog Charters, then get answers to all your questions at 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.

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). Next up on the itinerary: see the interesting displays at Chesapeake Bay Maritime Museum, admire the masterpieces at Academy Art Museum, do a tasting at Saint Michaels Winery, and indulge your thirst for a good beer at Eastern Shore Brewing.

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.

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.

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: Leonardtown (Leonardtown Wharf Park, Port of Leonardtown Winery, &more), Menokin (in Warsaw) and Hague (General's Ridge Vineyard and Winery & The Hague Winery). Next up on the itinerary: take an in-depth tour of Historic St. Mary's City, admire the majestic nature at Westmoreland State Park, learn about winemaking at Slack Winery, and contemplate the long history of The Dr. Samuel Mudd House & Museum.

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 go by car back home.