60 days in Maryland Itinerary

60 days in Maryland Itinerary

Created using Inspirock Maryland holiday planner

Plan created by another user. Make it yours
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

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11
nights
Baltimore

City of Firsts

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 Patuxent Branch Trail (in Columbia), Annapolis (Quiet Waters Park, U.S. Naval Academy, &more) and Sandy Spring (The Adventure Park at Sandy Spring & Underground Railroad Experience Trail Hikes). There's still lots to do: try to win big at Horseshoe Casino, observe the fascinating underwater world at National Aquarium, take in the waterfront activity at Inner Harbor, and get your game on at Urban Axes Baltimore.

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 fly. 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.

Things to do in Baltimore

Parks · Historic Sites · Museums · Outdoors

Side Trips

7
nights
Thurmont

Thurmont is a town in Frederick County, Maryland, United States. Get out of town with these interesting Thurmont side-trips: C&O Canal Hike at Point of Rocks Boat Ramp (in Point of Rocks), Rose Hill Cemetery (in Hagerstown) and Knoxville (Maryland Heights Trail & Frog Eye Farm). There's much more to do: take in the history at Antietam National Battlefield, pause for some photo ops at National Shrine Grotto of Lourdes, contemplate in the serene atmosphere at National Shrine of St. Elizabeth Ann Seton, and walk around Penn Mar Park.

To find photos, other places to visit, maps, and other tourist information, use the Thurmont journey planning app.

You can drive from Baltimore to Thurmont in 1.5 hours. In September, Thurmont is slightly colder than Baltimore - with highs of 72°F and lows of 56°F. Wrap up your sightseeing on the 28th (Sat) to allow time to travel to Cumberland.

Things to do in Thurmont

Parks · Historic Sites · Outdoors · Trails

Side Trips

8
nights
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. Get out of town with these interesting Cumberland side-trips: Big Pool (Fort Frederick State Park & Western Maryland Rail Trail), Green Ridge State Forest (in Flintstone) and Grantsville (House of Yoder & New Germany State Park). There's still lots to do: explore the landscape on two wheels at Great Allegheny Passage, don't miss a visit to Allegany Fairgrounds, see the interesting displays at Allegany Museum, and do a tasting at Charis Winery.

To find other places to visit, more things to do, ratings, and tourist information, read our Cumberland trip itinerary site.

You can drive from Thurmont to Cumberland in 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) to allow enough time to drive to Oakland.

Things to do in Cumberland

Parks · Nature · Outdoors · Trails

Side Trips

6
nights
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: explore the activities along Deep Creek Lake State Park, see the interesting displays at Garrett County Historical Museum, trot along with a tour on horseback, and admire the majestic nature at Swallow Falls State Park.

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 travel to Solomons.

Things to do in Oakland

Parks · Outdoors · Nature · Fun & Games

Side Trips

8
nights
Solomons

Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. Change things up with these side-trips from Solomons: Cambridge (Blackwater National Wildlife Refuge & Harriet Tubman Birthplace Marker), Prince Frederick (American Chestnut Land Trust & Edward T Hall Aquatic Center) and Scorpion Brewing (in Owings). The adventure continues: take in the waterfront activity at Spring Cove Marina, explore the galleries of Jefferson Patterson Park & Museum, take an in-depth tour of Historic St. Mary's City, and relax in the rural setting at Forrest Hall Farm & Orchard.

To see reviews, more things to do, and tourist information, go to the Solomons itinerary app.

Drive from Oakland to Solomons in 4.5 hours. Plan for a bit warmer temperatures traveling from Oakland in October, with highs in Solomons at 70°F and lows at 53°F. Finish up your sightseeing early on the 20th (Sun) so you can go by car to St. Michaels.

Things to do in Solomons

Parks · Museums · Outdoors · Wildlife

Side Trips

8
nights
St. Michaels

Explore St. Michaels' surroundings by going to Patuxent River Park (in Upper Marlboro), Neild Museum and Herb Garden (in Cambridge) and Stevensville (Lead Dog Charters & Matapeake Clubhouse and Beach).

For where to stay, more things to do, reviews, and other tourist information, you can read our St. Michaels online itinerary builder.

Drive from Solomons to St. Michaels in 2.5 hours. Expect a daytime high around 70°F in October, and nighttime lows around 53°F. Wrap up your sightseeing on the 28th (Mon) to allow time to drive to Ocean City.

Things to do in St. Michaels

Parks · Wildlife · Outdoors · Museums

Side Trips

11
nights
Ocean City

The White Marlin Capital of the World

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: Snow Hill (Bishop's Stock Fine Art, Craft & Wine & Julia A. Purnell Museum), Boxwood Gardens (in Princess Anne) and Salisbury (Salisbury Zoo, Ben's Red Swings Community Playground, &more). And it doesn't end there: take in the waterfront at Ocean City Boardwalk, play a few rounds at Rum Pointe Seaside Golf Links, take in the exciting artwork at Art League of Ocean City, and walk around Northside Park.

To find photos, more things to do, ratings, and tourist information, read our Ocean City travel route planner.

Traveling by car from St. Michaels to Ocean City takes 2 hours. Alternatively, you can do a combination of taxi and shuttle; or do a combination of taxi and bus. October in Ocean City sees daily highs of 69°F and lows of 53°F at night. You'll set off for home on the 8th (Fri).

Things to do in Ocean City

Outdoors · Parks · Theme Parks · Museums

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.