The player can travel and explore the 48 contiguous states of the United States of America, which was all of USA proper during the interwar period. Known areas include San Francisco, New York City, the Rockies/the American Southwest, the Midwest, and the Southeastern United States.
The game divides the continental United States into five regions, each containing cities and towns that act as concentrations of buildings for stories and act as stop points for riding the rails separated by farmland and wilderness.
Towns, like Portland, Maine, are spread across the map along the networks of roads and rails. Towns may act as an end-point for riding the rails but cannot be entered so they can only act as a start point if you hop the train.
Many stories in your inventory reference the nearest town to where you earned that story.
Cities, like Boston, MA, are also spread across the map along the network of roads and rails. Larger than towns, cities appear on your map screen and act as hubs for roads and railways. When you approach a city a prompt to enter that city appears above the city center. Entering the city brings you to that city's city screen and resets your spawn point to that city.
In each city you have four options:
- Explore will start a choose-your-own-adventure mini-game, at the end of which you will earn a story unique to that city. Each city can only be explored once.
- Earn Money will give you the option to look for work or panhandle as the first fork in another choose-your-own-adventure mini-game, at the end of which you may gain or lose money, health, or energy. You can earn money in each city only once.
- Train Station will give you a menu of destinations that you can spend money to safely travel to without using health or energy and saving quite a bit of time.
- Store will give you a menu of food and drinks that you can spend money on to restore health and energy. The first option in each city's store is themed for that city. Each food in each city can only be bought once.
Stories may reference a nearby city instead of town in your story inventory, and some of the city-specific stories reference the city or a landmark in that city by name.
State borders appear on the main map, but are more for visual reference than anything else. Many states are in more than one region.
Stories in your inventory may reference a state if no city or town was near the location you earned the story.
As you travel among the various regions the music, color palette, and country stories change to match the region's theme.
- States: Connecticut, Delaware, Maine, Maryland, Massachusetts, New Hampshire, New Jersey, New York, Pennsylvania, Rhode Island, Vermont, and parts of Ohio, Virginia, and West Virginia
- Towns: Portland, ME; Buffalo, NY; Philadelphia and Pittsburgh, PA; Richmond, VA; Burlington, VT
- States: Alabama, Arkansas, Florida, Georgia, Louisiana, Mississippi, North Carolina, South Carolina, Tennessee, and parts of Kentucky, Missouri, Oklahoma, Texas, Virginia, and West Virginia
- Cities: Miami, FL; Atlanta, GA; New Orleans, LA; Memphis and Nashville, TN
- Towns: Birmingham, Mobile, and Montgomery, AL; Jacksonville, St. Petersburg, and Tallahassee, FL; Savannah, GA; Jackson, MS; Charlotte, NC
- States: Illinois, Indiana, Iowa, Kansas, Michigan, Minnesota, Nebraska, North Dakota, South Dakota, Wisconsin, and parts of Colorado, Kentucky, Missouri, Montana, New Mexico, Ohio, Oklahoma, Texas, West Virginia, and Wyoming
- Cities: Denver, CO; Chicago, IL; Detroit, MI, Minneapolis, MN; St. Louis, MO
- Towns: Cedar Rapids and Des Moines, IA; Indianapolis, IN; Louisville, KY; Duluth, MN; Kansas City, MO; Bismark, ND; Cleveland and Columbus, OH; Oklahoma City, OK; Pierre, SD; Amarillo and Dallas, TX; Milwaukee, WI
- States: Arizona and parts of California, Colorado, Nevada, New Mexico, Oklahoma, Texas, and Utah
- Cities: Los Angeles, CA; Santa Fe, NM; Las Vegas, NV; El Paso and San Antonio, TX
- Towns: Phoenix, AZ; San Diego, CA; Shiprock, NM; Houston, TX; Salt Lake City, UT
- States: Idaho, Oregon, Washington, and parts of California, Montana, Nevada, Utah, and Wyoming
- Cities: San Francisco, CA; Boise, ID; Seattle, WA
- Towns: Billings and Helena, MT; Portland, OR; Spokane, WA
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