7 days in Maryland Itinerary

7 days in Maryland Itinerary

Created using Inspirock Maryland trip itinerary planner

Make it your trip
St. Michaels
— 2 nights
Ocean City
— 2 nights
— 1 night
— 1 night


St. Michaels

— 2 nights
You'll discover tucked-away gems like Lyon Rum Distillery and Saint Michaels Winery. Step out of the city life by going to Terrapin Nature Park and Boat Tours & Water Sports. Step out of St. Michaels with an excursion to Blackwater National Wildlife Refuge in Cambridge--about 52 minutes away.

To find ratings, other places to visit, reviews, and tourist information, read St. Michaels vacation maker.

Buffalo to St. Michaels is an approximately 3-hour flight. You can also drive; or do a combination of taxi, train, and bus. Traveling from Buffalo in September, things will get a bit warmer in St. Michaels: highs are around 80°F and lows about 62°F. Finish your sightseeing early on the 12th (Sun) to allow enough time to drive to Ocean City.

Things to do in St. Michaels

Breweries & Distilleries · Parks · Wildlife · Outdoors

Side Trips

Ocean City

— 2 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.
Start off your visit on the 13th (Mon): play a few rounds at Rum Pointe Seaside Golf Links and then admire the majestic nature at Assateague State Park. On your second day here, get outside with Outdoor Activities and then enjoy the sand and surf at Ocean City Beach.

To find other places to visit, reviews, ratings, and more tourist information, go to the Ocean City visit planner.

Drive from St. Michaels to Ocean City in 2 hours. Alternatively, you can do a combination of taxi and shuttle; or do a combination of taxi and bus. In September, daily temperatures in Ocean City can reach 78°F, while at night they dip to 64°F. Wrap up your sightseeing on the 14th (Tue) early enough to travel to Cumberland.

Things to do in Ocean City

Outdoors · Parks · Golf · Nature

Side Trip


— 1 night
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. Kick off your visit on the 15th (Wed): explore the landscape on two wheels at Great Allegheny Passage, sample the fine beverages at Charis Winery & Distillery, and then admire the majestic nature at Rocky Gap State Park.

For other places to visit, traveler tips, and other tourist information, read our Cumberland trip itinerary maker app.

Getting from Ocean City to Cumberland by car takes about 4.5 hours. Other options: do a combination of car and flight. Traveling from Ocean City in September, you can expect nighttime temperatures to be little chillier in Cumberland, with lows of 56°F. Wrap up your sightseeing on the 15th (Wed) to allow time to drive to Oakland.

Things to do in Cumberland

Parks · Breweries & Distilleries · Wineries · Trails


— 1 night
Oakland is a town in the west-central part of Garrett County, Maryland. Start off your visit on the 16th (Thu): contemplate the waterfront views at Deep Creek Lake State Park and then admire the majestic nature at Swallow Falls State Park.

For ratings, other places to visit, and more tourist information, read Oakland trip builder.

Traveling by car from Cumberland to Oakland takes 1.5 hours. Expect slightly colder weather when traveling from Cumberland in September: highs in Oakland hover around 68°F, while lows dip to 52°F. Cap off your sightseeing on the 16th (Thu) early enough to travel back home.

Things to do in Oakland

Parks · Nature

Maryland travel guide

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.