26 days in Maryland Itinerary

26 days in Maryland Itinerary

Created using Inspirock Maryland trip planner

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Make it your trip
Drive
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
Drive

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Oakland

— 2 nights
Oakland is a town in the west-central part of Garrett County, Maryland. Visiting Swallow Falls State Park and Deep Creek Lake State Park will get you outdoors. You'll explore the less-touristy side of things at Great Allegheny Passage and Rocky Gap State Park. Take a break from Oakland with a short trip to Spruce Forest Artisan Village in Grantsville, about 42 minutes away. There's still lots to do: look for gifts at FireFly Farms Market.

To find other places to visit, ratings, photos, and more tourist information, read our Oakland trip planner.

Washington to Oakland is an approximately 2.5-hour car ride. Plan for slightly colder temperatures traveling from Washington in September, with highs in Oakland at 68°F and lows at 52°F. Wrap up your sightseeing on the 3rd (Fri) early enough to travel to Frederick.

Things to do in Oakland

Parks · Nature · Historic Sites · Outdoors

Side Trips

Frederick

— 5 nights
Frederick is a city and the county seat of Frederick County in the U.S. state of Maryland. Museum-lovers will appreciate National Museum of Civil War Medicine and Washington County Museum of Fine Arts. Popular historic sites such as Historic Downtown Frederick and Antietam National Cemetery are in your itinerary. You'll find plenty of places to visit near Frederick: RIO Washingtonian Center (in Gaithersburg), Chesapeake & Ohio Canal National Historical Park (in Williamsport) and Big Cork Vineyards (in Rohrersville). There's lots more to do: view the masterpieces at Weinberg Center for the Arts, take in the history at Monocacy National Battlefield, take an in-depth tour of National Shrine of St. Elizabeth Ann Seton, and hunt for treasures at Pennsylvania Dutch Market.

For maps, reviews, and tourist information, use the Frederick trip builder website.

Getting from Oakland to Frederick by car takes about 2.5 hours. Traveling from Oakland in September, you will find days in Frederick are somewhat warmer (80°F), and nights are about the same (57°F). Wrap up your sightseeing on the 8th (Wed) 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.
Visiting Quiet Waters Park and B&A Trail will get you outdoors. Do some cultural sightseeing at Maryland State House and The Kunta Kinte - Alex Haley Memorial. Explore the numerous day-trip ideas around Annapolis: Dutch Country Farmers Market (in Laurel) and Vino 301 Wine Concierge - Tours (in Bowie). And it doesn't end there: take in nature's colorful creations at William Paca House & Garden, take in the spiritual surroundings of St. Anne's Church, get a new perspective on things with Boat Tours & Water Sports, and steep yourself in history at Hammond-Harwood House.

To find traveler tips, ratings, where to stay, and tourist information, read Annapolis driving holiday site.

Traveling by car from Frederick to Annapolis takes 1.5 hours. Alternatively, you can take a bus; or take a bus. Plan for somewhat warmer nights when traveling from Frederick in September since evenings lows in Annapolis dip to 66°F. Finish your sightseeing early on the 13th (Mon) so you can drive to St. Michaels.

Things to do in Annapolis

Historic Sites · Outdoors · Parks · Tours

Side Trips

St. Michaels

— 4 nights
Get some cultural insight at Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center. Eschew the tourist crowds and head to Boat Tours & Water Sports and Saint Michaels Winery. Step out of St. Michaels to go to Stevensville and see Terrapin Nature Park, which is approximately 46 minutes away.

To find more things to do, maps, photos, and tourist information, refer to the St. Michaels trip planner.

You can drive from Annapolis to St. Michaels in 1.5 hours. Expect a daytime high around 80°F in September, and nighttime lows around 62°F. Finish your sightseeing early on the 17th (Fri) so you can drive to Ocean City.

Things to do in St. Michaels

Museums · Breweries & Distilleries · Outdoors · Spas

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.
Step out of the city life by going to Assateague State Park and Rum Pointe Seaside Golf Links. Do some cultural sightseeing at Ocean City Life-Saving Station Museum and Main Street Berlin. Venture out of the city with trips to Salisbury (Ward Museum of Wildfowl Art & Salisbury Zoo). There's lots more to do: take a leisurely stroll along Oceanic Fishing Pier, play a few rounds at Lost Treasure Golf, cast your line with a fishing tour, and walk around Northside Park.

To find photos, maps, traveler tips, and tourist information, use the Ocean City trip planner.

Traveling by car from St. Michaels to Ocean City takes 2 hours. Alternatively, you can do a combination of taxi and shuttle; or do a combination of taxi and bus. In September, plan for daily highs up to 78°F, and evening lows to 64°F. Finish your sightseeing early on the 23rd (Thu) to allow enough time to travel to Solomons.

Things to do in Ocean City

Outdoors · Parks · Wildlife · Tours

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. You'll explore and learn at Calvert Marine Museum and Drum Point Lighthouse and Patuxent River Naval Air Museum. Get a sense of the local culture at Annmarie Garden and Historic St. Mary's City. Explore the numerous day-trip ideas around Solomons: Blackwater National Wildlife Refuge (in Cambridge) and Janes Island State Park (in Crisfield).

To see maps, reviews, traveler tips, and other tourist information, you can read our Solomons online visit planner.

Getting from Ocean City to Solomons by car takes about 3.5 hours. In September, daily temperatures in Solomons can reach 79°F, while at night they dip to 63°F. Finish up your sightseeing early on the 26th (Sun) so you can travel back home.

Things to do in Solomons

Museums · Parks · Historic Sites · 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.