57 days in United States Itinerary

57 days in United States Itinerary

Created using Inspirock United States holiday maker

Make it your trip
Fly
1
Chicago
— 11 nights
Fly to Washington Dulles International Airport, Drive to Cumberland
2
Cumberland
— 4 nights
Drive
3
Sharpsburg
— 4 nights
Drive
4
Baltimore
— 6 nights
Drive
5
Ocean City
— 3 nights
Drive
6
Cape May
— 6 nights
Drive
7
Asbury Park
— 5 nights
Drive
8
Princeton
— 6 nights
Drive
9
New York City
— 9 nights
Fly

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Chicago

— 11 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, don't miss a visit to Buckingham Fountain, get curious at Field Museum, and walk around Millennium Park.

To find reviews, other places to visit, traveler tips, and more tourist information, you can read our Chicago road trip app.

Sydney, Australia to Chicago is an approximately 23-hour flight. The time zone difference when traveling from Sydney to Chicago is minus 16 hours. Traveling from Sydney in July, things will get somewhat warmer in Chicago: highs are around 33°C and lows about 22°C. Wrap up your sightseeing on the 12th (Mon) to allow time to travel to Cumberland.

Things to do in Chicago

Parks · Museums · Historic Sites · Childrens Museums

Side Trips

Cumberland

— 4 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. Change things up with these side-trips from Cumberland: Schoolhouse Earth (in Friendsville), Herrington Manor State Park (in Oakland) and New Germany State Park (in Grantsville). There's still lots to do: hike along Great Allegheny Passage, stroll around Hagerstown City Park, brush up on your knowledge of spirits at Charis Winery & Distillery, and stroll through Green Ridge State Forest.

To see where to stay, more things to do, traveler tips, and other tourist information, use the Cumberland online trip itinerary builder.

Use the Route module to find suitable travel options from Chicago to Cumberland. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Cumberland. In July in Cumberland, expect temperatures between 35°C during the day and 21°C at night. Cap off your sightseeing on the 16th (Fri) early enough to go by car to Sharpsburg.

Things to do in Cumberland

Parks · Nature · Outdoors · Trails

Side Trips

Sharpsburg

— 4 nights
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Explore Sharpsburg's surroundings by going to Fort Frederick State Park (in Big Pool), Lockhouse 49 (in Clear Spring) and C&O Canal Hike at Point of Rocks Boat Ramp (in Point of Rocks). On the 17th (Sat), spend a day delving into the history of Antietam National Battlefield. There's lots more to do: steep yourself in history at Tolson's Chapel, take some stellar pictures from Annapolis Rock, relax in the rural setting at Frog Eye Farm, and do a tasting at Orchid Cellar Meadery and Winery.

For photos, other places to visit, ratings, and other tourist information, go to the Sharpsburg journey planning app.

Traveling by car from Cumberland to Sharpsburg takes 1.5 hours. In July, plan for daily highs up to 36°C, and evening lows to 22°C. Wrap up your sightseeing on the 20th (Tue) early enough to drive to Baltimore.

Things to do in Sharpsburg

Parks · Nature · Historic Sites · Wineries

Side Trips

Baltimore

— 6 nights

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.
Explore Baltimore's surroundings by going to Historic Downtown Frederick (in Frederick), National Fallen Firefighters Memorial (in Emmitsburg) and Roddy Road Covered Bridge (in Thurmont). Pack the 25th (Sun) with family-friendly diversions at The Adventure Park at Sandy Spring. There's still lots to do: sample the fine beverages at Sagamore Spirit Distillery, get curious at System Source Computer Museum, explore the world behind art at The Walters Art Museum, and brush up on your military savvy at Historic Ships in Baltimore.

For where to stay, reviews, other places to visit, and tourist information, read our Baltimore online driving holiday planner.

Drive from Sharpsburg to Baltimore in 1.5 hours. Plan for somewhat warmer nights when traveling from Sharpsburg in July since evenings lows in Baltimore dip to 27°C. Finish your sightseeing early on the 26th (Mon) so you can drive to Ocean City.

Things to do in Baltimore

Museums · Theme Parks · Historic Sites · Parks

Side Trips

Ocean City

— 3 nights

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.
Go for a jaunt from Ocean City to Salisbury to see Pemberton Historical Park about 52 minutes away. There's lots more to do: look for all kinds of wild species at Ayers Creek Adventures, admire the majestic nature at Assateague State Park, play a few rounds at Rum Pointe Seaside Golf Links, and walk around Northside Park.

To see traveler tips, photos, and more tourist information, you can read our Ocean City trip website.

Traveling by car from Baltimore to Ocean City takes 3 hours. Alternatively, you can take a bus. While traveling from Baltimore, expect little chillier days and about the same nights in Ocean City, ranging from highs of 34°C to lows of 24°C. Wrap up your sightseeing on the 29th (Thu) early enough to travel to Cape May.

Things to do in Ocean City

Parks · Outdoors · Shopping · Golf

Side Trips

Cape May

— 6 nights

The Nation's Oldest Seashore Resort

Cape May represents the other Jersey Shore--the one you don't see on TV--the one with a rich history and a refined, relaxed atmosphere.
Step out of Cape May to go to Sea Isle City and see Spas & Wellness, which is approximately 30 minutes away. And it doesn't end there: get interesting insight from Tours, head outdoors with EcoVentures, identify plant and animal life at South Cape May Meadows, and learn about wildlife with up-close encounters at Cape May County Park & Zoo.

To find other places to visit, maps, more things to do, and more tourist information, use the Cape May tour itinerary planner.

You can drive from Ocean City to Cape May in 3 hours. In July, plan for daily highs up to 33°C, and evening lows to 24°C. Finish your sightseeing early on the 4th (Wed) so you can drive to Asbury Park.

Things to do in Cape May

Parks · Outdoors · Beaches · Nature

Side Trips

Asbury Park

— 5 nights
Asbury Park is a city in Monmouth County, New Jersey, United States, located on the Jersey Shore and part of the New York City Metropolitan Area. Change things up with these side-trips from Asbury Park: Raritan Bay Waterfront Park (in South Amboy), Highlands (Hartshorne Woods Park, Twin Lights Historic Site, &more) and Henry Hudson Trail (in Marlboro). There's still lots to do: get your game on at Silverball Retro Arcade Asbury Park, admire the natural beauty at Deep Cut Gardens, stroll around Holmdel Park, and grab your bike and head to Bliss Price Arboretum and Wildlife Sanctuary.

To find where to stay, other places to visit, maps, and other tourist information, go to the Asbury Park holiday app.

You can drive from Cape May to Asbury Park in 2 hours. Alternatively, you can take a bus. In August, plan for daily highs up to 32°C, and evening lows to 21°C. Finish your sightseeing early on the 9th (Mon) so you can drive to Princeton.

Things to do in Asbury Park

Parks · Outdoors · Fun & Games · Beaches

Side Trips

Princeton

— 6 nights

College Town

Best known as the home of Princeton University, the town of Princeton centers around the Ivy League school and its stone, vine-covered buildings.
Change things up with these side-trips from Princeton: Far Hills (Leonard J. Buck Garden & Golf House Museum), Duke Island Park (in Bridgewater) and Bamboo Brook Outdoor Education Center (in Chester). Next up on the itinerary: gain insight at Princeton University, walk around Hamilton Veterans Park, admire the masterpieces at Princeton University Art Museum, and steep yourself in history at Washington Crossing Historic Park.

To see photos, traveler tips, maps, and other tourist information, read Princeton trip planner.

Drive from Asbury Park to Princeton in 1.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 33°C in August, and nighttime lows around 20°C. Finish your sightseeing early on the 15th (Sun) to allow enough time to drive to New York City.

Things to do in Princeton

Parks · Museums · Outdoors · Historic Sites

Side Trips

New York City

— 9 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Explore New York City's surroundings by going to Philadelphia (Todd House, Independence Hall, &more) and Bronx Zoo (in Bronx). The adventure continues: go for a walk through Central Park, make a trip to Times Square, enjoy breathtaking views from Empire State Building, and contemplate the long history of 9/11 Memorial.

To see ratings, where to stay, and more tourist information, read New York City online trip itinerary planner.

Drive from Princeton to New York City in 1.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Princeton in August, expect somewhat warmer with lows of 25°C in New York City. Wrap up your sightseeing on the 24th (Tue) to allow time to fly back home.

Things to do in New York City

Parks · Museums · Historic Sites · Zoos & Aquariums

Side Trips

United States travel guide

4.5
Specialty Museums · Beaches · Historic Sites
More than the country of car-packed streets seen in TV shows and movies, the United States of America is a complex and diverse home to over 300 million people living in a wide range of landscapes and climates. From its big-city skyscrapers to its sprawling natural parks, the country's ''melting pot'' combines many ethnic groups that share a strong sense of national identity despite their cultural differences. A country of road trips and big blue skies, the United States harbors orderly cities filled with restaurants, parks, museums, and innumerable sightseeing opportunities, as well as pristine natural areas perfect for a holiday in the great outdoors. To see as much as you can of this diverse land quickly, drive over some of the more than 6 million km (4 million mi) of highways leading through deserts, mountain peaks, fertile fields, and giant urban centers.

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.

New Jersey travel guide

3.9
Casinos · Shopping Malls · Beaches
The Garden State
Often overshadowed by its legendary neighbor, New York, New Jersey holds its own as a land of thriving industrial cities, sprawling farmland, and lively coastal towns. Called the Garden State, New Jersey is a hub of entertainment and cultural attractions for the east coast, from the famous sandy beaches and carnival-like atmosphere of the Jersey Shore to alluring Atlantic City, the Las Vegas of the east. New Jersey also boasts a wealth of historical places to visit, including battle sites and memorials, such as George Washington's Revolutionary War headquarters.