60 days in Maryland Itinerary

60 days in Maryland Itinerary

Created using Inspirock Maryland trip planner

Make it your trip
Drive
1
Solomons
— 8 nights
Drive
2
Ocean City
— 10 nights
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3
Cambridge
— 9 nights
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4
Kennedyville
— 8 nights
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5
Baltimore
— 14 nights
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Sharpsburg
— 10 nights
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Solomons

— 8 nights
Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. Visiting Jefferson Patterson Park & Museum and Chesapeake Beach Railway Trail will get you outdoors. Deepen your sense of the past at sights like Calvert Marine Museum and Drum Point Lighthouse and The Dr. Samuel Mudd House & Museum. Venture out of the city with trips to Slack Winery (in Ridge), Newburg (Governor Harry W. Nice Memorial Bridge & Maryland Veterans Memorial Museum) and Port Tobacco (Thomas Stone National Historic Site & Historic Port Tobacco Village). The adventure continues: do a tasting at Port of Leonardtown Winery, head outdoors with American Chestnut Land Trust, stroll through Merkle Wildlife Sanctuary, and immerse yourself in nature at St. Clement's Island State Park.

For photos, other places to visit, maps, and tourist information, read our Solomons trip planner.

Washington DC to Solomons is an approximately 1.5-hour car ride. Expect a daytime high around 43°F in January, and nighttime lows around 28°F. Cap off your sightseeing on the 27th (Mon) early enough to travel to Ocean City.

Things to do in Solomons

Parks · Historic Sites · Museums · Outdoors

Side Trips

Ocean City

— 10 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.
Take a break from the city and head to Ocean City Beach and GlenRiddle Golf Club. Art League of Ocean City and Bishop's Stock Fine Art, Craft & Wine are good opportunities to explore the local culture. Explore Ocean City's surroundings by going to Snow Hill (Furnace Town Living Heritage Village, Julia A. Purnell Museum, &more), Pocomoke City (Delmarva Discovery Center & Sturgis One Room School Museum) and Salisbury (Eastern Shore Baseball Hall of Fame Museum, Poplar Hill Mansion, &more). The adventure continues: walk around Northside Park, see the interesting displays at Ocean City Life-Saving Station Museum, learn about winemaking at Costa Ventosa Vineyard & Winery, and indulge your thirst for a good beer at Burley Oak Brewing Company.

For more things to do, traveler tips, where to stay, and other tourist information, read Ocean City road trip planner.

You can drive from Solomons to Ocean City in 3.5 hours. In January, plan for daily highs up to 43°F, and evening lows to 27°F. Finish your sightseeing early on the 6th (Thu) to allow enough time to drive to Cambridge.

Things to do in Ocean City

Museums · Outdoors · Parks · Historic Sites

Side Trips

Cambridge

— 9 nights
Cambridge is a city in Dorchester County, Maryland, United States. Visit Old Wye Church and The Third Haven Friends Meeting House for their historical value. Step out of the city life by going to Blackwater National Wildlife Refuge and Martinak State Park. Get out of town with these interesting Cambridge side-trips: St. Michaels (Saint Michaels Winery, Lyon Rum Distillery, &more), Salisbury (Pemberton Historical Park, Ward Museum of Wildfowl Art, &more) and Wye Mills (Wye Oak State Park & Old Wye Grist Mill). There's much more to do: relax and rejuvenate at some of the top local wellness centers, do a tasting at Layton's Chance Vineyard and Winery, examine the collection at Crisfield Heritage Foundation, and explore the world behind art at Academy Art Museum.

To find ratings, more things to do, reviews, and more tourist information, read our Cambridge trip itinerary builder app.

Drive from Ocean City to Cambridge in 1.5 hours. Expect a daytime high around 46°F in February, and nighttime lows around 31°F. Cap off your sightseeing on the 15th (Sat) early enough to travel to Kennedyville.

Things to do in Cambridge

Museums · Parks · Historic Sites · Wineries

Side Trips

Kennedyville

— 8 nights
Take a break from the city and head to Elk Neck State Park and Painted Sky Alpaca Farm & Fiber Mill. Satisfy your inner culture vulture at Crow Farm and Vineyard and Winery and Dove Valley Winery. Venture out of the city with trips to Rock Hall (Ferry Park & Eastern Neck National Wildlife Refuge), Adkins Arboretum (in Ridgely) and C&D Canal Museum (in Chesapeake City).

To see traveler tips, photos, other places to visit, and more tourist information, read our Kennedyville trip planning tool.

Drive from Cambridge to Kennedyville in 1.5 hours. In February, plan for daily highs up to 44°F, and evening lows to 29°F. Cap off your sightseeing on the 23rd (Sun) early enough to travel to Baltimore.

Things to do in Kennedyville

Parks · Outdoors · Museums · Wineries

Side Trips

Baltimore

— 14 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.
Step out of the city life by going to Fort McHenry National Monument and Historic Shrine and Audubon Naturalist Society Woodend Sanctuary. Visit Fell's Point and Homewood Museum for their historical value. Explore Baltimore's surroundings by going to Columbia (Lake Kittamaqundi, Robinson Nature Center, &more), Annapolis (Annapolis Historic District, Wild Bird Center, &more) and Centennial Park (in Ellicott City). There's lots more to do: try to win big at Horseshoe Casino, brush up on your knowledge of spirits at Blackwater Distilling & Tavern, stop by Mount Vernon Cultural District, and explore the world behind art at The Walters Art Museum.

To see maps, traveler tips, photos, and more tourist information, refer to the Baltimore trip itinerary maker site.

You can drive from Kennedyville to Baltimore in 2 hours. In February in Baltimore, expect temperatures between 46°F during the day and 32°F at night. Cap off your sightseeing on the 8th (Sun) early enough to go by car to Sharpsburg.

Things to do in Baltimore

Parks · Wildlife · Historic Sites · Neighborhoods

Side Trips

Sharpsburg

— 10 nights
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Antietam National Battlefield and Antietam National Cemetery will appeal to history buffs. Get outdoors at Orchid Cellar Meadery and Winery and P.B. Dye Golf Club. Explore Sharpsburg's surroundings by going to National Shrine of St. Elizabeth Ann Seton (in Emmitsburg), Rocky Gap Casino Resort (in Flintstone) and Frederick (Historic Downtown Frederick, Clue IQ: An Escape Room Experience, &more). And it doesn't end there: contemplate the long history of Tolson's Chapel, learn about winemaking at Linganore Winecellars, play a few rounds at Worthington Manor Golf Club, and stroll the grounds of Rose Hill Cemetery.

For maps, other places to visit, ratings, and more tourist information, you can read our Sharpsburg online vacation planner.

You can drive from Baltimore to Sharpsburg in 1.5 hours. Plan for slightly colder nights when traveling from Baltimore in March since evenings lows in Sharpsburg dip to 31°F. On the 18th (Wed), wrap the sightseeing up by early afternoon so you can drive back home.

Things to do in Sharpsburg

Historic Sites · Parks · Wineries · Outdoors

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.