15 days in Maryland Itinerary

15 days in Maryland Itinerary

Created using Inspirock Maryland trip planner

Plan created by another user. Make it yours

Route & dates

1
Baltimore
— 3 nights
2
Cumberland
— 3 nights
3
Hagerstown
— 3 nights
4
St. Michaels
— 2 nights
5
Ocean City
— 3 nights

3
nights
Baltimore

Baltimore ©
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.
Step out of Baltimore with an excursion to U.S. Naval Academy in Annapolis--about 40 minutes away. There's still lots to do: try your luck at Horseshoe Casino, admire the masterpieces at The Walters Art Museum, relax in the rural setting at Weber's Cider Mill Farm, and wander the streets of Fell's Point.

To see photos, traveler tips, more things to do, and more tourist information, read our Baltimore trip itinerary maker website.

New York City to Baltimore is an approximately 3-hour train ride. You can also drive; or fly. In October, plan for daily highs up to °F, and evening lows to °F. Finish your sightseeing early on the 7th (Wed) to allow enough time to travel to Cumberland.

Things to do in Baltimore

Parks Historic Sites Zoos & Aquariums

Side Trips

U.S. Naval Academy, Weber's Cider Mill Farm
Highlights from your plan
Sagamore Spirit Distillery ©
Sagamore Spirit Distillery
Horseshoe Casino ©
Horseshoe Casino
The Walters Art Museum ©
The Walters Art Museum

3
nights
Cumberland

Cumberland ©
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. Venture out of the city with trips to New Germany State Park (in Grantsville) and Oakland (Deep Creek Lake State Park & Swallow Falls State Park). And it doesn't end there: grab your bike and head to Great Allegheny Passage, get lost in a book at Allegany County Library System - LaVale Library, contemplate the long history of Paw Paw Tunnel, and admire the majestic nature at Rocky Gap State Park.

To see more things to do and tourist information, read Cumberland day trip planning site.

You can drive from Baltimore to Cumberland in 2.5 hours. Traveling from Baltimore in October, expect a bit cooler with lows of °F in Cumberland. Wrap up your sightseeing on the 10th (Sat) early enough to drive to Hagerstown.

Things to do in Cumberland

Parks Nature Trails

Side Trips

Oakland, Allegany County Library System - LaVale Library, New Germany State Park, Dans Rock Scenic Overlook
Highlights from your plan
Great Allegheny Passage ©
Great Allegheny Passage
Paw Paw Tunnel ©
Paw Paw Tunnel
Charis Winery ©
Charis Winery

3
nights
Hagerstown

Hagerstown ©
Hagerstown is a city in Washington County, Maryland, United States. Explore the numerous day-trip ideas around Hagerstown: Frederick (Clue IQ: An Escape Room Experience & National Museum of Civil War Medicine) and National Shrine Grotto of Lourdes (in Emmitsburg). Next up on the itinerary: explore the wealth of natural beauty at C&O Canal Trust, take in the views from Burnside's Bridge, walk around Penn Mar Park, and take in the history at Antietam National Battlefield.

To find more things to do, where to stay, maps, and more tourist information, use the Hagerstown road trip planner.

You can drive from Cumberland to Hagerstown in 1.5 hours. In October, daytime highs in Hagerstown are °F, while nighttime lows are °F. Cap off your sightseeing on the 13th (Tue) early enough to travel to St. Michaels.

Things to do in Hagerstown

Parks Nature Historic Sites

Side Trips

Frederick, Sharpsburg, Penn Mar Park, National Shrine Grotto of Lourdes
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
C&O Canal Trust ©
C&O Canal Trust
Clue IQ: An Escape Room Experience ©
Clue IQ: An Escape Room Experience

2
nights
St. Michaels

St. Michaels ©
Kick off your visit on the 14th (Wed): relax and rejuvenate at some of the top local wellness centers, see the interesting displays at Chesapeake Bay Maritime Museum, thenget a new perspective on things with Boat Tours & Water Sports, and finally brush up on your knowledge of spirits at Lyon Rum Distillery & Tasting Room. Keep things going the next day: take an in-depth tour of 1879 Hooper Strait Lighthouse, look for all kinds of wild species at Phillips Wharf Environmental Center, and then relax in the rural setting at P.A. Bowen Farmstead.

To find maps, other places to visit, photos, and more tourist information, read our St. Michaels online attractions planner.

Drive from Hagerstown to St. Michaels in 2.5 hours. In October in St. Michaels, expect temperatures between °F during the day and °F at night. Wrap up your sightseeing on the 15th (Thu) early enough to drive to Ocean City.

Things to do in St. Michaels

Museums Wildlife Spas

Side Trips

P.A. Bowen Farmstead, Spas & Wellness, Phillips Wharf Environmental Center
Highlights from your plan
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
Boat Tours & Water Sports
Lyon Rum Distillery & Tasting Room ©
Lyon Rum Distillery & Tasting Room

3
nights
Ocean City

Ocean City ©
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.
Explore the numerous day-trip ideas around Ocean City: Salisbury (Pemberton Historical Park, Ben's Red Swings Community Playground, &more). There's much more to do: enjoy the sand and surf at Ocean City Beach, tee off at Eagle's Landing Golf Course, admire the majestic nature at Assateague State Park, and stroll around Northside Park.

For maps, where to stay, ratings, and tourist information, go to the Ocean City day trip planning site.

Drive from St. Michaels to Ocean City in 2 hours. Alternatively, you can do a combination of taxi and bus. In October, plan for daily highs up to °F, and evening lows to °F. Finish up your sightseeing early on the 18th (Sun) so you can go by car back home.

Things to do in Ocean City

Parks Outdoors Museums

Side Trips

Salisbury, Berlin
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Ocean City Boardwalk ©
Ocean City Boardwalk
Eagle's Landing Golf Course ©
Eagle's Landing Golf Course

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