60 days in Maryland Itinerary

60 days in Maryland Itinerary

Created using Inspirock Maryland holiday planner

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Route & dates

60 days in Maryland Itinerary

Start: New York City
train:  2​h 45​min
1
Baltimore
— 11 nights
Drive:  1​h 15​min
2
Thurmont
— 7 nights
Drive:  2​h 15​min
3
Cumberland
— 8 nights
Drive:  1​h 15​min
4
Oakland
— 6 nights
Drive:  4​h 15​min
5
Solomons
— 8 nights
Drive:  2​h 15​min
6
St. Michaels
— 8 nights
Drive:  1​h 45​min
7
Ocean City
— 11 nights
Drive:  4​h 30​min
End: New York City

11
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.
Venture out of the city with trips to Annapolis (Quiet Waters Park, U.S. Naval Academy, & more), Patuxent Branch Trail (in Columbia) and Sandy Spring (The Adventure Park at Sandy Spring & Underground Railroad Experience Trail Hikes). There's much more to do: try to win big at Horseshoe Casino, observe the fascinating underwater world at National Aquarium, get your game on at Urban Axes Baltimore, and wander the streets of Fell's Point.

For maps, reviews, and more tourist information, read our Baltimore trip builder website .

New York City to Baltimore is an approximately 3-hour train ride. You can also drive; or fly. In September, plan for daily highs up to 81°F, and evening lows to 66°F. Wrap up your sightseeing on the 21st (Sat) early enough to drive to Thurmont.

Things to do in Baltimore

Parks Historic Sites Museums

Side Trips

Annapolis, Sandy Spring, Patuxent Branch Trail, Downs Park, Baltimore Sports & Novelty
Highlights from your plan
Urban Axes Baltimore ©
Urban Axes Baltimore
Horseshoe Casino ©
Horseshoe Casino
Sagamore Spirit Distillery ©
Sagamore Spirit Distillery

7
nights
Thurmont

Thurmont ©
Thurmont is a town in Frederick County, Maryland, United States. Explore Thurmont's surroundings by going to Knoxville (Maryland Heights Trail & Frog Eye Farm), Rose Hill Cemetery (in Hagerstown) and C&O Canal Hike at Point of Rocks Boat Ramp (in Point of Rocks). There's lots more to do: put a fun spin on your tour with Clue IQ: An Escape Room Experience, admire the natural beauty at Surreybrooke Gardens, make a trip to Community Bridge Mural, and walk around Carrol Creek Linear Park.

To find more things to do, photos, other places to visit, and tourist information, go to the Thurmont trip builder app .

Drive from Baltimore to Thurmont in 1.5 hours. Plan for a bit cooler temperatures traveling from Baltimore in September, with highs in Thurmont at 72°F and lows at 56°F. Finish your sightseeing early on the 28th (Sat) so you can travel to Cumberland.

Things to do in Thurmont

Parks Historic Sites Outdoors

Side Trips

Frederick, Sharpsburg, Emmitsburg, Knoxville, C&O Canal Hike at Point of Rocks Boat Ramp
Highlights from your plan
Clue IQ: An Escape Room Experience ©
Clue IQ: An Escape Room Experience
Antietam National Battlefield ©
Antietam National Battlefield
National Shrine Grotto of Lourdes ©
National Shrine Grotto of Lourdes

8
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. Explore Cumberland's surroundings by going to Green Ridge State Forest (in Flintstone), Grantsville (House of Yoder & New Germany State Park) and Big Pool (Fort Frederick State Park & Western Maryland Rail Trail). There's lots more to do: grab your bike and head to Great Allegheny Passage, make a trip to Allegany Fairgrounds, do a tasting at Charis Winery, and examine the collection at Allegany Museum.

To see more things to do, traveler tips, and tourist information, go to the Cumberland travel route planner .

Drive from Thurmont to Cumberland in 2 hours. When traveling from Thurmont in September, plan for a bit warmer days in Cumberland, with highs around 80°F, while nights are about the same with lows around 56°F. Finish up your sightseeing early on the 6th (Sun) so you can go by car to Oakland.

Things to do in Cumberland

Parks Nature Trails

Side Trips

Grantsville, Big Pool, LaVale, Flintstone, Allegany County Library System - Frostburg Library
Highlights from your plan
New Germany State Park ©
New Germany State Park
Paw Paw Tunnel ©
Paw Paw Tunnel
Charis Winery ©
Charis Winery

6
nights
Oakland

Oakland ©
Oakland is a town in the west-central part of Garrett County, Maryland. Oakland is known for nature, museums, and golf. Your plan includes some of its best attractions: immerse yourself in nature at Swallow Falls State Park, see the interesting displays at Garrett County Historical Museum, tee off at Lodestone Golf Course, and take a pleasant ride with a tour on horseback.

For other places to visit, where to stay, ratings, and more tourist information, use the Oakland tour app .

Traveling by car from Cumberland to Oakland takes 1.5 hours. Traveling from Cumberland in October, things will get little chillier in Oakland: highs are around 57°F and lows about 42°F. Finish your sightseeing early on the 12th (Sat) to allow enough time to travel to Solomons.

Things to do in Oakland

Parks Outdoors Nature

Side Trips

McHenry, Simon Pearce Factory Outlet and Glassblowing, The Discovery Center, Schoolhouse Earth
Highlights from your plan
Swallow Falls State Park ©
Swallow Falls State Park
Deep Creek Lake State Park ©
Deep Creek Lake State Park
Garrett County Museum of Transportation ©

8
nights
Solomons

Solomons ©
Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. Venture out of the city with trips to Cambridge (Blackwater National Wildlife Refuge & Harriet Tubman Birthplace Marker), Scorpion Brewing (in Owings) and Prince Frederick (American Chestnut Land Trust & Edward T Hall Aquatic Center). There's lots more to do: enjoy the sea views from Calvert Marine Museum and Drum Point Lighthouse, get outside with Casey Michelle Charters, go for a stroll along the water at Spring Cove Marina, and walk around Greenwell State Park.

For where to stay, maps, other places to visit, and other tourist information, refer to the Solomons route builder app .

You can drive from Oakland to Solomons in 4.5 hours. In October, Solomons is a bit warmer than Oakland - with highs of 70°F and lows of 53°F. Finish your sightseeing early on the 20th (Sun) so you can drive to St. Michaels.

Things to do in Solomons

Parks Museums Outdoors

Side Trips

Leonardtown, Cambridge, Prince Frederick, Chesapeake Beach, Scorpion Brewing
Highlights from your plan
Blackwater National Wildlife Refuge ©
Spring Cove Marina ©
Spring Cove Marina

8
nights
St. Michaels

St. Michaels ©
Explore St. Michaels' surroundings by going to Neild Museum and Herb Garden (in Cambridge), Stevensville (Lead Dog Charters & Matapeake Clubhouse and Beach) and Jug Bay Wetlands Sanctuary (in Lothian).

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

You can drive from Solomons to St. Michaels in 2.5 hours. October in St. Michaels sees daily highs of 70°F and lows of 53°F at night. Finish up your sightseeing early on the 28th (Mon) so you can go by car to Ocean City.

Things to do in St. Michaels

Parks Wildlife Museums

Side Trips

Chestertown, Annapolis, Easton, Wye Mills, Stevensville
Highlights from your plan
Neild Museum and Herb Garden ©
Neild Museum and Herb Garden
Lyon Distilling Company ©
Lyon Distilling Company
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum

11
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.
You'll find plenty of places to visit near Ocean City: Salisbury (Salisbury Zoo, Ben's Red Swings Community Playground, & more), Snow Hill (Bishop's Stock Fine Art, Craft & Wine & Julia A. Purnell Museum) and Boxwood Gardens (in Princess Anne). There's still lots to do: kick back and relax at Ocean City Beach, glide through the air with a parasailing or paragliding tour, tee off at Eagle's Landing Golf Course, and browse the collection at Ocean City Branch Library.

To see more things to do, other places to visit, reviews, and more tourist information, refer to the Ocean City day trip planning tool .

Traveling by car from St. Michaels to Ocean City takes 2 hours. Alternatively, you can take a bus. October in Ocean City sees daily highs of 69°F and lows of 53°F at night. On the 8th (Fri), wrap the sightseeing up by early afternoon so you can drive back home.

Things to do in Ocean City

Outdoors Parks Theme Parks

Side Trips

Salisbury, Berlin, Crisfield, Snow Hill, Boxwood Gardens
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Ocean City Boardwalk ©
Ocean City Boardwalk
Stand-Up Paddleboarding

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