16 days in Maryland Itinerary

16 days in Maryland Itinerary

Created using Inspirock Maryland trip planner
Make it your trip
Train
1
Baltimore
— 4 nights
Drive
2
Hagerstown
— 4 nights
Drive
3
Oakland
— 2 nights
Drive
4
Ocean City
— 5 nights
Drive

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Baltimore — 4 nights

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.
Change things up with these side-trips from Baltimore: Billy Goat Trail (in Potomac), Annapolis (Seasons Olive Oil and Vinegar Tap Room, Maryland State House, &more) and Silver Spring (Wat Thai of Washington, D.C. & Big Escape Rooms). There's still lots to do: admire the masterpieces at The Walters Art Museum, shop like a local with Fell's Point, view the masterpieces at Waverly Street Gallery, and don't miss a visit to National Katyn Memorial.

To see other places to visit, maps, reviews, and more tourist information, read our Baltimore itinerary planner.

Philadelphia to Baltimore is an approximately 2-hour train ride. You can also drive; or take a bus. In December in Baltimore, expect temperatures between 50°F during the day and 37°F at night. Finish your sightseeing early on the 26th (Sat) to allow enough time to drive to Hagerstown.
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Parks · Neighborhoods · Zoos & Aquariums · Historic Sites
Side Trips

Hagerstown — 4 nights

Hagerstown is a city in Washington County, Maryland, United States. Get out of town with these interesting Hagerstown side-trips: Emmitsburg (National Shrine of St. Elizabeth Ann Seton & National Shrine Grotto of Lourdes), Surreybrooke Gardens (in Middletown) and Frederick (Roads and Rails Museum, Historic Downtown Frederick, &more). There's much more to do: explore the world behind art at Washington County Museum of Fine Arts, take some stellar pictures from High Rock Overlook, take in the history at Antietam National Battlefield, and take in the pleasant sights at The Hagerstown Cultural Trail.

You can plan Hagerstown trip in no time by asking Inspirock to help create your itinerary.

Getting from Baltimore to Hagerstown by car takes about 1.5 hours. Traveling from Baltimore in December, expect slightly colder with lows of 32°F in Hagerstown. Finish up your sightseeing early on the 30th (Wed) so you can go by car to Oakland.
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Historic Sites · Parks · Nature · Museums
Side Trips

Oakland — 2 nights

Oakland is a town in the west-central part of Garrett County, Maryland. Kick off your visit on the 31st (Thu): revel in the low prices at Simon Pearce Factory Outlet and Glassblowing, then stop by Schoolhouse Earth, then stroll through Wisp Resort, and finally explore the activities along Deep Creek Lake State Park. Get ready for a full day of sightseeing on the next day: examine the collection at Garrett County Historical Museum, then see the interesting displays at Garrett County Museum of Transportation, then examine the collection at The Oakland B&O Railroad Museum, and finally admire the majestic nature at Swallow Falls State Park.

To find photos, reviews, more things to do, and more tourist information, you can read our Oakland route planner.

Traveling by car from Hagerstown to Oakland takes 2.5 hours. Traveling from Hagerstown in December, expect Oakland to be a bit cooler, temps between 38°F and 26°F. Finish your sightseeing early on the 1st (Fri) so you can drive to Ocean City.
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Parks · Museums · Nature · Shopping
Side Trips

Ocean City — 5 nights

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.
Venture out of the city with trips to Snow Hill (Bishop's Stock Fine Art, Craft & Wine & Julia A. Purnell Museum), Pocomoke City (Delmarva Discovery Museum & Chesapeake Bay Farms) and Crisfield Heritage Foundation (in Crisfield). There's still lots to do: walk around Northside Park, see the interesting displays at Ocean City Life-Saving Station Museum, take a leisurely stroll along Ocean City Boardwalk, and relax and rejuvenate at OC Massage.

For more things to do, ratings, other places to visit, and tourist information, refer to the Ocean City trip planner.

You can drive from Oakland to Ocean City in 5.5 hours. Traveling from Oakland in January, expect Ocean City to be somewhat warmer, temps between 43°F and 27°F. Finish up your sightseeing early on the 6th (Wed) so you can go by car back home.
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Museums · Parks · Outdoors · Fun & Games
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.
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