18 days in Maryland Itinerary

18 days in Maryland Itinerary

Created using Inspirock Maryland visit planner
Make it your trip
Drive
1
Ocean City
— 3 nights
Drive
2
St. Michaels
— 2 nights
Drive
3
Baltimore
— 6 nights
Drive
4
Sharpsburg
— 3 nights
Drive
5
Cumberland
— 3 nights
Drive

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Ocean City — 3 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.
Bring the kids along to Ocean City Beach and Ocean City Chamber of Commerce. Venture out of the city with trips to Salisbury (Pemberton Historical Park & Chesapeake Ghost Walks), Crisfield (Crisfield Heritage Foundation & Janes Island State Park) and Chesapeake Bay Farms (in Pocomoke City). The adventure continues: take in the waterfront at Ocean City Boardwalk, stroll around Northside Park, see the interesting displays at Ocean City Life-Saving Station Museum, and tee off at Eagle's Landing Golf Course.

Before you visit Ocean City, use our trip planner to discover what you can do and see there.

Washington DC to Ocean City is an approximately 3-hour car ride. You can also take a bus; or do a combination of train and bus. October in Ocean City sees daily highs of 69°F and lows of 53°F at night. Finish up your sightseeing early on the 31st (Sat) so you can go by car to St. Michaels.
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Parks · Outdoors · Nature · Tours
Side Trips

St. Michaels — 2 nights

On the 1st (Sun), stop by Simpatico Itay's Finest, relax and rejuvenate at some of the top local wellness centers, then experience rural life at Outstanding Dreams Farm, then admire the majestic nature at Martinak State Park, and finally don't miss a visit to Old Wye Church. Here are some ideas for day two: get a new perspective on things with Boat Tours & Water Sports, then see the interesting displays at Chesapeake Bay Maritime Museum, and then savor the flavors at Eastern Shore Food Tours - Eating Easton.

For photos, reviews, traveler tips, and tourist information, refer to the St. Michaels trip planner.

Getting from Ocean City to St. Michaels by car takes about 2 hours. Other options: do a combination of shuttle and taxi; or do a combination of bus and taxi. In October, daytime highs in St. Michaels are 70°F, while nighttime lows are 53°F. Finish up your sightseeing early on the 2nd (Mon) so you can go by car to Baltimore.
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Tours · Museums · Parks · Nature
Side Trips

Baltimore — 6 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.
You'll visit kid-friendly attractions like National Aquarium and The Adventure Park at Sandy Spring. You'll find plenty of places to visit near Baltimore: Annapolis (James Brice House & U.S. Naval Academy), Big Escape Rooms (in Silver Spring) and Green Meadows Petting Farm (in Ijamsville). There's lots more to do: admire the masterpieces at The Walters Art Museum, experience rural life at Knill's Farm Market, see the interesting displays at American Visionary Art Museum, and explore the striking landscape of Fort McHenry National Monument and Historic Shrine.

For traveler tips, more things to do, and more tourist information, read Baltimore holiday planner.

You can drive from St. Michaels to Baltimore in 2 hours. Another option is to do a combination of taxi and bus. November in Baltimore sees daily highs of 57°F and lows of 43°F at night. Finish your sightseeing early on the 8th (Sun) to allow enough time to drive to Sharpsburg.
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Parks · Historic Sites · Theme Parks · Nature
Side Trips

Sharpsburg — 3 nights

Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Step out of Sharpsburg with an excursion to C&O Canal Hike at Point of Rocks Boat Ramp in Point of Rocks--about 34 minutes away. There's lots more to do: witness the site of a historic battle at Antietam National Battlefield, immerse yourself in nature at Washington Monument State Park, take in the views from Burnside's Bridge, and explore the different monuments and memorials at Antietam National Cemetery.

To see maps, traveler tips, other places to visit, and more tourist information, go to the Sharpsburg online road trip planner.

You can drive from Baltimore to Sharpsburg in 1.5 hours. Traveling from Baltimore in November, Sharpsburg is a bit cooler at night with lows of 34°F. Finish up your sightseeing early on the 11th (Wed) so you can go by car to Cumberland.
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Historic Sites · Parks · Nature · Outdoors
Side Trips

Cumberland — 3 nights

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. Kids will appreciate attractions like Great Allegheny Passage and Swallow Falls State Park. Change things up with these side-trips from Cumberland: Deep Creek Lake State Park (in Oakland), New Germany State Park (in Grantsville) and Hagerstown (C&O Canal Trust & The Hagerstown Cultural Trail). There's more to do: steep yourself in history at Gordon-Roberts House.

To see traveler tips, where to stay, photos, and tourist information, go to the Cumberland day trip tool.

Getting from Sharpsburg to Cumberland by car takes about 1.5 hours. Expect a daytime high around 54°F in November, and nighttime lows around 34°F. Wrap up your sightseeing on the 14th (Sat) early enough to drive back home.
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Parks · Nature · Outdoors · Trails
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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