21 days in Maryland Itinerary

21 days in Maryland Itinerary

Created using Inspirock Maryland itinerary planner

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Route & dates

21 days in Maryland Itinerary

Start: Washington DC
Drive:  1​h
1
Annapolis
— 3 nights
Drive:  2​h 30​min
2
Ocean City
— 6 nights
Drive:  2​h 15​min
3
Solomons
— 3 nights
Drive:  4​h 30​min
4
Cumberland
— 3 nights
Drive:  2​h 15​min
5
Frederick
— 5 nights
Drive:  1​h
End: Washington DC

3
nights
Annapolis

Annapolis ©
Capital of the United States for one year from 1783 to 1784, Annapolis has played a vital role in U.S.
You'll explore the less-touristy side of things at Walking tours and Lyon Distilling Company. Get outdoors at Adkins Arboretum and Eastern Neck National Wildlife Refuge. You'll find plenty of places to visit near Annapolis: Wye Oak State Park (in Wye Mills) and Phillips Wharf Environmental Center (in Tilghman). The adventure continues: explore the activities along Susan Campbell Park, take in the architecture and atmosphere at St. Mary's Church, take in the views from Chesapeake Bay Bridge, and steep yourself in history at St. John's College.

To see where to stay, photos, traveler tips, and tourist information, you can read our Annapolis trip builder .

Washington DC to Annapolis is an approximately 1-hour car ride. You can also take a bus. In September, daytime highs in Annapolis are 78°F, while nighttime lows are 66°F. Wrap up your sightseeing on the 11th (Wed) early enough to drive to Ocean City.

Things to do in Annapolis

Parks Wildlife Historic Sites

Side Trips

Adkins Arboretum, Phillips Wharf Environmental Center, Wye Oak State Park, Lyon Distilling Company, Eastern Neck National Wildlife Refuge
Highlights from your plan
Phillips Wharf Environmental Center ©
Adkins Arboretum ©
Adkins Arboretum
Eastern Neck National Wildlife Refuge ©

6
nights
Ocean City

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.
Discover out-of-the-way places like Waterskiing & Jetskiing and Cape May Point State Park. Step out of the city life by going to Stand-Up Paddleboarding and Eagle's Landing Golf Course. Change things up with these side-trips from Ocean City: Junction and Breakwater Trail (in Rehoboth Beach), Bethany Beach Nature Center (in Bethany Beach) and Cape May Bird Observatory (in Cape May Point). Next up on the itinerary: admire the majestic nature at Fenwick Island State Park, see the interesting displays at Ripley's Believe it or Not! Ocean City, make a splash at West OC Watersports, and take in the waterfront at Oceanic Fishing Pier.

To see where to stay, photos, more things to do, and more tourist information, read our Ocean City journey planner.

You can drive from Annapolis to Ocean City in 2.5 hours. Alternatively, you can take a bus. In September, plan for daily highs up to 78°F, and evening lows to 64°F. Wrap up your sightseeing on the 17th (Tue) to allow time to travel to Solomons.

Things to do in Ocean City

Outdoors Parks Golf

Side Trips

Cape May Point, Bethany Beach Nature Center, Junction and Breakwater Trail, Fenwick Island State Park
Highlights from your plan
Stand-Up Paddleboarding
Fenwick Island State Park ©
Fenwick Island State Park
Waterskiing & Jetskiing

3
nights
Solomons

Solomons ©
Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. Take a break from the city and head to Janes Island State Park and Flag Ponds Nature Park. Discover out-of-the-way places like Westmoreland State Park and Spring Cove Marina. Change things up with these side-trips from Solomons: Choptank River Lighthouse (in Cambridge) and Hughlett Point Natural Area (in Reedville). It doesn't end there: shop like a local with Annmarie Garden.

To see photos, other places to visit, maps, and more tourist information, go to the Solomons road trip tool .

Drive from Ocean City to Solomons in 3.5 hours. In September, daily temperatures in Solomons can reach 79°F, while at night they dip to 63°F. Finish your sightseeing early on the 20th (Fri) so you can travel to Cumberland.

Things to do in Solomons

Parks Nature Wildlife

Side Trips

Flag Ponds Nature Park, Choptank River Lighthouse, Hughlett Point Natural Area, Janes Island State Park, Westmoreland State Park
Highlights from your plan
Janes Island State Park ©
Janes Island State Park
Flag Ponds Nature Park ©
Flag Ponds Nature Park
Westmoreland State Park ©
Westmoreland State Park

3
nights
Cumberland

Cumberland ©
Cumberland, officially the City of Cumberland, is a western gateway city and seat of Allegany County, Maryland, United States and the primary city of the Cumberland, MD-WV Metropolitan Statistical Area. You'll explore the less-touristy side of things at Great Allegheny Passage and Sideling Hill Welcome Center. Escape the urban bustle at Rocky Gap State Park and Linn Run State Park. Step out of Cumberland with an excursion to Laurel Hill State Park in Somerset--about 1h 05 min away. There's much more to do: examine the collection at Allegany Museum, learn about winemaking at Charis Winery, steep yourself in history at George Washington's Headquarters, and pick up some local products at Hill Top Fruit Market.

To see where to stay, ratings, photos, and tourist information, read Cumberland tour itinerary planning tool .

Drive from Solomons to Cumberland in 3.5 hours. Traveling from Solomons in September, you can expect nighttime temperatures to be slightly colder in Cumberland, with lows of 56°F. Finish your sightseeing early on the 23rd (Mon) to allow enough time to travel to Frederick.

Things to do in Cumberland

Parks Nature Outdoors

Side Trips

Hill Top Fruit Market, Laurel Hill State Park, Linn Run State Park
Highlights from your plan
Great Allegheny Passage ©
Great Allegheny Passage
Laurel Hill State Park ©
Laurel Hill State Park
Rocky Gap State Park ©
Rocky Gap State Park

5
nights
Frederick

Frederick ©
Frederick is a city and the county seat of Frederick County in the U.S. Get outdoors at East Coast Exotic Animal Rescue and Armory Canal Trail. Eschew the tourist crowds and head to Appalachian National Scenic Trail and Community Bridge Mural. You'll find plenty of places to visit near Frederick: St. Peter's Roman Catholic Church (in Harpers Ferry), National Sporting Library & Museum (in Middleburg) and St. Francis Xavier Catholic Church (in Gettysburg). There's lots more to do: explore the different monuments and memorials at Mount Olivet Cemetery, partake in some friendly competition at Surelocked In Escape Games, look for all kinds of wild species at Audubon Naturalist Society Rust Nature Sanctuary, and pause for some serene contemplation at Evangelical Lutheran Church.

For photos, traveler tips, maps, and other tourist information, read our Frederick trip planner .

You can drive from Cumberland to Frederick in 1.5 hours. In September in Frederick, expect temperatures between 80°F during the day and 57°F at night. Wrap up your sightseeing on the 28th (Sat) to allow time to drive back home.

Things to do in Frederick

Parks Wildlife Historic Sites

Side Trips

Harpers Ferry, Audubon Naturalist Society Rust Nature Sanctuary, Washington Monument State Park, National Sporting Library & Museum, East Coast Exotic Animal Rescue
Highlights from your plan
Appalachian National Scenic Trail ©
Appalachian National Scenic Trail
East Coast Exotic Animal Rescue ©
East Coast Exotic Animal Rescue
Washington Monument State Park ©
Washington Monument State Park

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