26 days in Maryland Itinerary

26 days in Maryland Itinerary

Created using Inspirock Maryland trip itinerary maker

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1
Oakland
— 2 nights
Drive
2
Frederick
— 5 nights
Drive
3
Annapolis
— 5 nights
Drive
4
St. Michaels
— 4 nights
Drive
5
Ocean City
— 6 nights
Drive
6
Solomons
— 3 nights
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Oakland

— 2 nights
Oakland is a town in the west-central part of Garrett County, Maryland. Take a break from the city and head to Swallow Falls State Park and Great Allegheny Passage. Eschew the tourist crowds and head to Deep Creek Lake State Park and Spruce Forest Artisan Village. Step out of Oakland with an excursion to Rocky Gap State Park in Cumberland--about 1h 20 min away. There's more to do: stop by FireFly Farms Market.

To find where to stay, traveler tips, maps, and tourist information, read Oakland itinerary builder tool.

Washington to Oakland is an approximately 2.5-hour car ride. In September, Oakland is little chillier than Washington - with highs of 68°F and lows of 52°F. Finish up your sightseeing early on the 6th (Mon) so you can travel to Frederick.

Things to do in Oakland

Parks · Nature · Shopping · Outdoors

Side Trips

Frederick

— 5 nights
Frederick is a city and the county seat of Frederick County in the U.S. state of Maryland. You'll explore the less-touristy side of things at Historic Downtown Frederick and Monocacy National Battlefield. Your cultural itinerary includes sights like National Museum of Civil War Medicine and Antietam National Cemetery. You'll find plenty of places to visit near Frederick: RIO Washingtonian Center (in Gaithersburg), Hagerstown (Washington County Museum of Fine Arts & Pennsylvania Dutch Market) and Chesapeake & Ohio Canal National Historical Park (in Williamsport). There's much more to do: view the masterpieces at Weinberg Center for the Arts, learn about winemaking at Big Cork Vineyards, and explore the galleries of National Shrine of St. Elizabeth Ann Seton.

Discover how to plan a Frederick trip in just a few steps with Inspirock's itinerary builder.

Traveling by car from Oakland to Frederick takes 2.5 hours. When traveling from Oakland in September, plan for a bit warmer days and about the same nights in Frederick: temperatures range from 80°F by day to 57°F at night. Wrap up your sightseeing on the 11th (Sat) to allow time to drive to Annapolis.

Things to do in Frederick

Museums · Historic Sites · Shopping · Wineries

Side Trips

Annapolis

— 5 nights
Capital of the United States for one year from 1783 to 1784, Annapolis has played a vital role in U.S. history.
Do some cultural sightseeing at Maryland State House and William Paca House & Garden. Get in touch with nature at Quiet Waters Park and B&A Trail. Get out of town with these interesting Annapolis side-trips: Vino 301 Wine Concierge - Tours (in Bowie) and Dutch Country Farmers Market (in Laurel). And it doesn't end there: take in the spiritual surroundings of St. Anne's Church, steep yourself in history at The Kunta Kinte - Alex Haley Memorial, and get a new perspective on things with Boat Tours & Water Sports.

To see ratings, other places to visit, where to stay, and tourist information, go to the Annapolis day trip planning website.

You can drive from Frederick to Annapolis in 1.5 hours. Alternatively, you can take a bus; or take a bus. Traveling from Frederick in September, Annapolis is somewhat warmer at night with lows of 66°F. Cap off your sightseeing on the 16th (Thu) early enough to go by car to St. Michaels.

Things to do in Annapolis

Historic Sites · Parks · Outdoors · Tours

Side Trips

St. Michaels

— 4 nights
Step out of the city life by going to Boat Tours & Water Sports and Terrapin Nature Park. Harriet Tubman Underground Railroad National Historical Park and Saint Michaels Winery are good opportunities to explore the local culture. Step out of St. Michaels to go to Cambridge and see Harriet Tubman Museum and Educational Center, which is approximately 36 minutes away.

To see where to stay, maps, traveler tips, and tourist information, read St. Michaels travel route builder app.

You can drive from Annapolis to St. Michaels in 1.5 hours. In September, daytime highs in St. Michaels are 80°F, while nighttime lows are 62°F. Finish your sightseeing early on the 20th (Mon) so you can drive to Ocean City.

Things to do in St. Michaels

Museums · Breweries & Distilleries · Outdoors · Parks

Side Trips

Ocean City

— 6 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.
Museum-lovers will get to explore Ocean City Life-Saving Station Museum and Ward Museum of Wildfowl Art. Step off the beaten path and head to Assateague State Park and Lost Treasure Golf. Go for a jaunt from Ocean City to Salisbury to see Salisbury Zoo about 40 minutes away. And it doesn't end there: tee off at Rum Pointe Seaside Golf Links, catch all the local highlights with Ayers Creek Adventures, take in the waterfront at Oceanic Fishing Pier, and sample the tasty concoctions at Burley Oak Brewing Company.

For maps, photos, other places to visit, and tourist information, use the Ocean City itinerary planner.

You can drive from St. Michaels to Ocean City in 2 hours. Other options are to do a combination of taxi and shuttle; or do a combination of taxi and bus. Expect a daytime high around 78°F in September, and nighttime lows around 64°F. Wrap up your sightseeing on the 26th (Sun) to allow time to travel to Solomons.

Things to do in Ocean City

Outdoors · Parks · Wildlife · Museums

Side Trips

Solomons

— 3 nights
Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. Appreciate the collections at Calvert Marine Museum and Drum Point Lighthouse and Patuxent River Naval Air Museum. Step off the beaten path and head to Annmarie Garden and Janes Island State Park. Step out of Solomons to go to Cambridge and see Blackwater National Wildlife Refuge, which is approximately 2 hours away. There's more to do: take an in-depth tour of Historic St. Mary's City.

To see more things to do, ratings, traveler tips, and other tourist information, read our Solomons trip builder website.

Traveling by car from Ocean City to Solomons takes 3.5 hours. In September, daytime highs in Solomons are 79°F, while nighttime lows are 63°F. Wrap up your sightseeing on the 29th (Wed) early enough to travel back home.

Things to do in Solomons

Museums · Parks · Shopping · 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.