14 days in Maryland Itinerary

14 days in Maryland Itinerary

Created using Inspirock Maryland trip planner

Make it your trip
Train
1
Baltimore
— 3 nights
Drive
2
Oakland
— 1 night
Drive
3
Cumberland
— 1 night
Drive
4
Hagerstown
— 1 night
Drive
5
Frederick
— 1 night
Drive
6
Silver Spring
— 1 night
Drive
7
Chesapeake Beach
— 1 night
Drive
8
Annapolis
— 1 night
Drive
9
St. Michaels
— 1 night
Drive
10
Ocean City
— 2 nights
Drive

S M T W T F S
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Baltimore

— 3 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.
You'll find plenty of places to visit near Baltimore: Washington DC (National World War II Memorial, National Air and Space Museum, &more). There's more to do: try your luck at Horseshoe Casino.

For other places to visit, traveler tips, more things to do, and more tourist information, you can read our Baltimore road trip planning tool.

Philadelphia to Baltimore is an approximately 2-hour train ride. You can also drive; or take a bus. August in Baltimore sees daily highs of 86°F and lows of 71°F at night. Wrap up your sightseeing on the 4th (Wed) to allow time to travel to Oakland.

Things to do in Baltimore

Museums · Parks · Zoos & Aquariums · Fun & Games

Side Trip

Oakland

— 1 night
Oakland is a town in the west-central part of Garrett County, Maryland. Start off your visit on the 5th (Thu): immerse yourself in nature at Herrington Manor State Park, then admire the majestic nature at Swallow Falls State Park, and then contemplate the waterfront views at Deep Creek Lake State Park.

To see traveler tips, maps, more things to do, and tourist information, read our Oakland road trip app.

Getting from Baltimore to Oakland by car takes about 3.5 hours. Traveling from Baltimore in August, things will get little chillier in Oakland: highs are around 72°F and lows about 57°F. Cap off your sightseeing on the 5th (Thu) early enough to go by car to Cumberland.

Things to do in Oakland

Nature · Parks

Cumberland

— 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 6th (Fri): brush up on your knowledge of spirits at Charis Winery & Distillery and then explore the landscape on two wheels at Great Allegheny Passage.

To see traveler tips, maps, photos, and more tourist information, refer to the Cumberland trip itinerary website.

Drive from Oakland to Cumberland in 1.5 hours. Expect somewhat warmer weather when traveling from Oakland in August: highs in Cumberland hover around 84°F, while lows dip to 62°F. Finish your sightseeing early on the 6th (Fri) so you can drive to Hagerstown.

Things to do in Cumberland

Trails · Parks · Outdoors · Breweries & Distilleries

Hagerstown

— 1 night
Hagerstown is a city in Washington County, Maryland, United States. Kick off your visit on the 7th (Sat): explore the wealth of natural beauty at C&O Canal Trust and then get a taste of the local shopping with Just LOOKIN' Gallery.

To see more things to do, where to stay, and tourist information, refer to the Hagerstown trip itinerary maker app.

You can drive from Cumberland to Hagerstown in 1.5 hours. In August, daily temperatures in Hagerstown can reach 84°F, while at night they dip to 65°F. Finish your sightseeing early on the 7th (Sat) to allow enough time to drive to Frederick.

Things to do in Hagerstown

Nature · Parks · Museums · Shopping

Frederick

— 1 night
Frederick is a city and the county seat of Frederick County in the U.S. state of Maryland. On the 8th (Sun), take in the history at Monocacy National Battlefield, sample the fine beverages at Dragon Distillery, LLC, stroll around Carroll Creek Linear Park, then sample the fine beverages at McClintock Distilling, and finally make a trip to Community Bridge Mural.

To find more things to do, photos, traveler tips, and tourist information, read our Frederick road trip planning tool.

Traveling by car from Hagerstown to Frederick takes an hour. In August in Frederick, expect temperatures between 84°F during the day and 63°F at night. Finish your sightseeing early on the 8th (Sun) so you can drive to Silver Spring.

Things to do in Frederick

Historic Sites · Parks · Breweries & Distilleries

Silver Spring

— 1 night
Silver Spring is an unincorporated community and census-designated place (CDP) located inside the Capital Beltway in Montgomery County, Maryland, United States. Start off your visit on the 9th (Mon): contemplate in the serene atmosphere at Wat Thai of Washington, D.C., walk around Wheaton Regional Park, then pause for some serene contemplation at St Camillus Church, and finally take a stroll around Silver Spring Civic Center.

For photos, traveler tips, reviews, and more tourist information, read our Silver Spring trip app.

Traveling by car from Frederick to Silver Spring takes an hour. August in Silver Spring sees daily highs of 84°F and lows of 65°F at night. Finish your sightseeing early on the 9th (Mon) so you can travel to Chesapeake Beach.

Things to do in Silver Spring

Historic Sites · Parks · Shopping

Chesapeake Beach

— 1 night
Chesapeake Beach is a town in Calvert County, Maryland. Kick off your visit on the 10th (Tue): take a memorable tour with Katherines Charter Fishing, head outdoors with American Chestnut Land Trust, and then cool off at Edward T Hall Aquatic Center.

To find ratings, maps, and tourist information, read our Chesapeake Beach journey planning site.

You can drive from Silver Spring to Chesapeake Beach in an hour. Expect a daytime high around 84°F in August, and nighttime lows around 65°F. Cap off your sightseeing on the 10th (Tue) early enough to go by car to Annapolis.

Things to do in Chesapeake Beach

Outdoors · Wildlife · Theme Parks · Tours

Side Trip

Annapolis

— 1 night
Capital of the United States for one year from 1783 to 1784, Annapolis has played a vital role in U.S. history.
Start off your visit on the 11th (Wed): identify plant and animal life at Wild Bird Center, see what you can catch with Family Fishing Adventures, then explore the activities along Susan Campbell Park, and finally deepen your knowledge of military history at U.S. Naval Academy.

To see photos, reviews, more things to do, and other tourist information, go to the Annapolis road trip app.

Drive from Chesapeake Beach to Annapolis in an hour. In August, daily temperatures in Annapolis can reach 82°F, while at night they dip to 70°F. Finish your sightseeing early on the 11th (Wed) so you can drive to St. Michaels.

Things to do in Annapolis

Wildlife · Parks · Museums · Tours

St. Michaels

— 1 night
On the 12th (Thu), get outside with Chesapeake Bay Environmental Center, indulge your thirst for a good beer at Eastern Shore Brewing, then sample the fine beverages at Lyon Rum Distillery, and finally get a new perspective on things with Boat Tours & Water Sports.

To find photos, ratings, reviews, and other tourist information, read our St. Michaels travel planning website.

You can drive from Annapolis to St. Michaels in 1.5 hours. August in St. Michaels sees daily highs of 84°F and lows of 67°F at night. Finish your sightseeing early on the 12th (Thu) to allow enough time to drive to Ocean City.

Things to do in St. Michaels

Outdoors · Breweries & Distilleries · Tours

Side Trip

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.
On the 13th (Fri), admire the majestic nature at Assateague State Park, stop by A Little Bit Sheepish, then get a dose of the wild on Ayers Creek Adventures, and finally play a few rounds at Rum Pointe Seaside Golf Links. Get ready for a full day of sightseeing on the 14th (Sat): walk around Northside Park, then examine the collection at Ocean City Life-Saving Station Museum, then kick back and relax at Ocean City Beach, and finally take a leisurely stroll along Ocean City Boardwalk.

To find more things to do, maps, traveler tips, and other tourist information, you can read our Ocean City tour 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 August in Ocean City, expect temperatures between 82°F during the day and 67°F at night. Wrap up your sightseeing on the 14th (Sat) early enough to drive back home.

Things to do in Ocean City

Parks · Outdoors · Wildlife · Nature

Side Trip

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.