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
Drive

S M T W T F S
20
21
22
23
24
25
26
27
28
29
30
31
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9

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.
Venture out of the city with trips to Annapolis (Annapolis Historic District, Susan Campbell Park, &more). There's still lots to do: try your luck at Horseshoe Casino, sample the fine beverages at Sagamore Spirit Distillery, admire nature's wide array of creatures at Inner Harbor, and wander the streets of Fell's Point.

To find where to stay, maps, photos, and more tourist information, go to the Baltimore road trip site.

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. Wrap up your sightseeing on the 26th (Sat) to allow time to travel to Oakland.
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 Market, 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.
Parks · Nature · Museums · Outdoors
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: Frederick (Historic Downtown Frederick & Escape This Frederick) and National Shrine Grotto of Lourdes (in Emmitsburg). 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.
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.
Museums · Historic Sites · Shopping · Parks
Side Trips

Ocean City — 4 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 Salisbury (Ward Museum of Wildfowl Art, Eastern Shore Baseball Hall of Fame Museum, &more), Delmarva Discovery Museum (in Pocomoke City) and Crisfield Heritage Foundation (in Crisfield). There's much more to do: stroll around Northside Park, view the masterpieces at Bishop's Stock Fine Art, Craft & Wine, examine the collection at Julia A. Purnell Museum, and kick back and relax at Ocean City Beach.

To find more things to do, traveler tips, other places to visit, and tourist information, read our Ocean City trip planner.

You can drive from St. Michaels to Ocean City in 2 hours. Other options are to do a combination of taxi and shuttle; or do a combination of taxi and bus. In January, daily temperatures in Ocean City can reach 43°F, while at night they dip to 27°F. Finish up your sightseeing early on the 6th (Wed) so you can go by car back home.
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.