60 days in Maryland Itinerary
Created using Inspirock Maryland holiday planner
Start: New York City
Train
1
Baltimore
— 11 nights
Drive
2
Thurmont
— 7 nights
Drive
3
Cumberland
— 8 nights
Drive
4
Oakland
— 6 nights
Drive
5
Solomons
— 8 nights
Drive
6
St. Michaels
— 8 nights
Drive
7
Ocean City
— 11 nights
Drive
End: New York City
Tue, Sep 10 - Fri, Nov 8
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View full calendar
Baltimore — 11 nights
©
City of Firsts
Venture out of the city with trips to Sandy Spring (The Adventure Park at Sandy Spring & Underground Railroad Experience Trail Hikes), Annapolis (Quiet Waters Park, U.S. Naval Academy, &more) and Patuxent Branch Trail (in Columbia). There's still lots to do: try to win big at Horseshoe Casino, observe the fascinating underwater world at National Aquarium, explore the world behind art at The Walters Art Museum, and wander the streets of Fell's Point.
To see other places to visit, where to stay, maps, and more tourist information, go to the Baltimore route maker website.
New York City to Baltimore is an approximately 3-hour train ride. You can also drive; or take a bus. In September, daily temperatures in Baltimore can reach 81°F, while at night they dip to 66°F. Finish your sightseeing early on the 21st (Sat) so you can drive to Thurmont.
more
To see other places to visit, where to stay, maps, and more tourist information, go to the Baltimore route maker website.
New York City to Baltimore is an approximately 3-hour train ride. You can also drive; or take a bus. In September, daily temperatures in Baltimore can reach 81°F, while at night they dip to 66°F. Finish your sightseeing early on the 21st (Sat) so you can drive to Thurmont.
Side Trips
Highlights from your trip
Thurmont — 7 nights
©
Get out of town with these interesting Thurmont side-trips: Rose Hill Cemetery (in Hagerstown), C&O Canal Hike at Point of Rocks Boat Ramp (in Point of Rocks) and Knoxville (Maryland Heights Trail & Frog Eye Farm).
For more things to do, maps, ratings, and more tourist information, refer to the Thurmont itinerary planner.
Getting from Baltimore to Thurmont by car takes about 1.5 hours. In September, Thurmont is a bit cooler than Baltimore - with highs of 72°F and lows of 56°F. Cap off your sightseeing on the 28th (Sat) early enough to go by car to Cumberland.
more
For more things to do, maps, ratings, and more tourist information, refer to the Thurmont itinerary planner.
Getting from Baltimore to Thurmont by car takes about 1.5 hours. In September, Thurmont is a bit cooler than Baltimore - with highs of 72°F and lows of 56°F. Cap off your sightseeing on the 28th (Sat) early enough to go by car to Cumberland.
Side Trips
Highlights from your trip
Cumberland — 8 nights
©
Get out of town with these interesting Cumberland side-trips: Big Pool (Fort Frederick State Park & Western Maryland Rail Trail) and Grantsville (House of Yoder & New Germany State Park).
To see maps, ratings, photos, and other tourist information, read our Cumberland trip itinerary planning tool.
Getting from Thurmont to Cumberland by car takes about 2 hours. When traveling from Thurmont in September, plan for somewhat warmer days and about the same nights in Cumberland: temperatures range from 80°F by day to 56°F at night. Finish your sightseeing early on the 6th (Sun) so you can drive to Oakland.
more
To see maps, ratings, photos, and other tourist information, read our Cumberland trip itinerary planning tool.
Getting from Thurmont to Cumberland by car takes about 2 hours. When traveling from Thurmont in September, plan for somewhat warmer days and about the same nights in Cumberland: temperatures range from 80°F by day to 56°F at night. Finish your sightseeing early on the 6th (Sun) so you can drive to Oakland.
Side Trips
Highlights from your trip
Oakland — 6 nights
©
Oakland is known for nature, adventure, and museums. Your trip includes some of its best attractions: explore the activities along Deep Creek Lake State Park, immerse yourself in nature at Swallow Falls State Park, enjoy some diversion at Adventure Sports Center International, and examine the collection at Garrett County Historical Museum.
To see maps and tourist information, use the Oakland trip maker website.
You can drive from Cumberland to Oakland in 1.5 hours. Traveling from Cumberland in October, expect Oakland to be little chillier, temps between 57°F and 42°F. Wrap up your sightseeing on the 12th (Sat) to allow time to drive to Solomons.
more
To see maps and tourist information, use the Oakland trip maker website.
You can drive from Cumberland to Oakland in 1.5 hours. Traveling from Cumberland in October, expect Oakland to be little chillier, temps between 57°F and 42°F. Wrap up your sightseeing on the 12th (Sat) to allow time to drive to Solomons.
Side Trips
Highlights from your trip
Solomons — 8 nights
©
Explore Solomons' surroundings by going to Prince Frederick (American Chestnut Land Trust & Edward T Hall Aquatic Center), Scorpion Brewing (in Owings) and Cambridge (Blackwater National Wildlife Refuge & Harriet Tubman Birthplace Marker).
To find more things to do, photos, ratings, and other tourist information, read Solomons trip planner.
Drive from Oakland to Solomons in 4.5 hours. Traveling from Oakland in October, things will get somewhat warmer in Solomons: highs are around 70°F and lows about 53°F. Finish your sightseeing early on the 20th (Sun) so you can drive to St. Michaels.
more
To find more things to do, photos, ratings, and other tourist information, read Solomons trip planner.
Drive from Oakland to Solomons in 4.5 hours. Traveling from Oakland in October, things will get somewhat warmer in Solomons: highs are around 70°F and lows about 53°F. Finish your sightseeing early on the 20th (Sun) so you can drive to St. Michaels.
Side Trips
Highlights from your trip
St. Michaels — 8 nights
©
You'll find plenty of places to visit near St. Michaels: Stevensville (Lead Dog Charters & Matapeake Clubhouse and Beach), Neild Museum and Herb Garden (in Cambridge) and Patuxent River Park (in Upper Marlboro).
For maps, traveler tips, where to stay, and tourist information, go to the St. Michaels driving holiday planning site.
Traveling by car from Solomons to St. Michaels takes 2.5 hours. In October, daily temperatures in St. Michaels can reach 70°F, while at night they dip to 53°F. Wrap up your sightseeing on the 28th (Mon) to allow time to drive to Ocean City.
more
For maps, traveler tips, where to stay, and tourist information, go to the St. Michaels driving holiday planning site.
Traveling by car from Solomons to St. Michaels takes 2.5 hours. In October, daily temperatures in St. Michaels can reach 70°F, while at night they dip to 53°F. Wrap up your sightseeing on the 28th (Mon) to allow time to drive to Ocean City.
Side Trips
Highlights from your trip
Ocean City — 11 nights
©
The White Marlin Capital of the World
You'll find plenty of places to visit near Ocean City: Snow Hill (Bishop's Stock Fine Art, Craft & Wine & Julia A. Purnell Museum), Salisbury (Salisbury Zoo, Ben's Red Swings Community Playground, &more) and Boxwood Gardens (in Princess Anne). And it doesn't end there: take a leisurely stroll along Ocean City Boardwalk, play a few rounds at Eagle's Landing Golf Course, view the masterpieces at Art League of Ocean City, and see what you can catch with a fishing tour.
For where to stay, traveler tips, photos, and more tourist information, you can read our Ocean City trip app.
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 October, plan for daily highs up to 69°F, and evening lows to 53°F. You will leave for home on the 8th (Fri).
more
For where to stay, traveler tips, photos, and more tourist information, you can read our Ocean City trip app.
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 October, plan for daily highs up to 69°F, and evening lows to 53°F. You will leave for home on the 8th (Fri).
Side Trips
Highlights from your trip
Maryland travel guide
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.
