16 days in Maryland Itinerary

16 days in Maryland Itinerary

Created using Inspirock Maryland attractions planner

Make it your trip
Train
1
Baltimore
— 4 nights
Drive
2
Oakland
— 2 nights
Drive
3
Hagerstown
— 3 nights
Drive
4
St. Michaels
— 2 nights
Drive
5
Ocean City
— 4 nights
Fly

S M T W T F S
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31
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Baltimore

— 4 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.
Venture out of the city with trips to Annapolis (Annapolis Historic District, Susan Campbell Park, &more). Next up on the itinerary: try to win big at Horseshoe Casino, sample the fine beverages at Sagamore Spirit Distillery, admire nature's wide array of creatures at Inner Harbor, and soothe aching muscles at ROAM Fitness.

For photos, ratings, reviews, and more tourist information, refer to the Baltimore trip planner.

Philadelphia to Baltimore is an approximately 2-hour train ride. You can also drive; or take a bus. December in Baltimore sees daily highs of 50°F and lows of 37°F at night. Cap off your sightseeing on the 26th (Sat) early enough to travel to Oakland.

Things to do in Baltimore

Parks · Neighborhoods · Zoos & Aquariums · 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 27th (Sun): explore the activities along Deep Creek Lake State Park, stop by FireFly Farms, then hit the slopes at Wisp Resort, and finally admire the majestic nature at Swallow Falls State Park. Here are some ideas for day two: examine the collection at Garrett County Historical Museum, then have fun and explore at The Discovery Center, and then contemplate the long history of Spruce Forest Artisan Village.

Plan my trip to Oakland with suggested itineraries provided by Inspirock.

Drive from Baltimore to Oakland in 3.5 hours. Traveling from Baltimore in December, expect Oakland to be little chillier, temps between 38°F and 26°F. Finish up your sightseeing early on the 28th (Mon) so you can travel to Hagerstown.

Things to do in Oakland

Parks · Museums · Nature · Winter Sports

Side Trips

Hagerstown

— 3 nights
Hagerstown is a city in Washington County, Maryland, United States. You'll find plenty of places to visit near Hagerstown: National Shrine Grotto of Lourdes (in Emmitsburg) and Frederick (Historic Downtown Frederick & Escape This Frederick). The adventure continues: admire the masterpieces at Washington County Museum of Fine Arts, take in the history at Antietam National Battlefield, and don't miss a visit to The Hagerstown Cultural Trail.

For traveler tips, other places to visit, photos, and tourist information, refer to the Hagerstown sightseeing app.

Drive from Oakland to Hagerstown in 2.5 hours. Plan for a bit warmer temperatures traveling from Oakland in December, with highs in Hagerstown at 46°F and lows at 32°F. Cap off your sightseeing on the 31st (Thu) early enough to travel to St. Michaels.

Things to do in Hagerstown

Historic Sites · Nature · Parks · Museums

Side Trips

St. Michaels

— 2 nights
On the 1st (Fri), see the interesting displays at The Oxford Museum, take in nature's colorful creations at Neild Museum and Herb Garden, then steep yourself in history at The Third Haven Friends Meeting House, and finally examine the collection at Tuckahoe Steam and Gas Association. Get ready for a full day of sightseeing on the next day: see the interesting displays at Tilghman Watermans Museum, stop by The Amish Market, then relax and rejuvenate at some of the top local wellness centers, and finally sample the fine beverages at Lyon Rum Distillery.

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

Traveling by car from Hagerstown to St. Michaels takes 2.5 hours. In December, daily temperatures in St. Michaels can reach 50°F, while at night they dip to 36°F. Finish your sightseeing early on the 2nd (Sat) to allow enough time to drive to Ocean City.

Things to do in St. Michaels

Museums · Shopping · Parks · Historic Sites

Side Trips

Ocean City

— 4 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.
Venture out of the city with trips to Salisbury (Ward Museum of Wildfowl Art, Eastern Shore Baseball Hall of Fame Museum, &more), Delmarva Discovery Museum (in Pocomoke City) and Chesapeake Ghost Walks (in Marion Station). Next up on the itinerary: walk around Northside Park, enjoy the sand and surf at Ocean City Beach, see the interesting displays at Ocean City Life-Saving Station Museum, and indulge in some personalized pampering at OC Massage.

To see traveler tips and more tourist information, use the Ocean City trip itinerary builder website.

You can 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 January in Ocean City, expect temperatures between 43°F during the day and 27°F at night. Wrap up your sightseeing on the 6th (Wed) early enough to fly back home.

Things to do in Ocean City

Museums · Parks · Beaches · Outdoors

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.