Despite producing four Hall of Famers and numerous other major league talents, very little is written about the Eastern Shore Baseball League (defunct since 1949). A quick Google search gets you only a few relevant hits, interspersed among a plethora of links for present-day little league and high school teams. Amazon.com boasts two books (one of which is in stock), while the Wikipedia page consists of a terse paragraph followed by a quick list of teams. In other words, you can't find much on the Eastern Shore League through the internet or books. If you want to learn about it, you need to go see it for yourself... or at least what remains. Once you're in the area, you can pretty much do it all in one very full day.
I'll start with a quick history lesson. The ESBL had three incarnations: 1922-1928, 1937-1941, and 1946-1949. Although it was known as a classy and competitive league, it was never able to achieve economic sustainability. The Class D league (now known as Rookie League) was represented by all three states of the Delmarva Peninsula. On any given season, the league had between six and eight teams, ranging from slightly larger towns such as Dover, Delaware to remote and sparsely populated communities like Parksley, Virginia and Pokomoke City, Maryland. While the segregated white teams played during the week, the Eastern Shore Negro League held their games over weekends and on holidays - when African-American fans were more able to come in from Baltimore and DC.
I'll start with a quick history lesson. The ESBL had three incarnations: 1922-1928, 1937-1941, and 1946-1949. Although it was known as a classy and competitive league, it was never able to achieve economic sustainability. The Class D league (now known as Rookie League) was represented by all three states of the Delmarva Peninsula. On any given season, the league had between six and eight teams, ranging from slightly larger towns such as Dover, Delaware to remote and sparsely populated communities like Parksley, Virginia and Pokomoke City, Maryland. While the segregated white teams played during the week, the Eastern Shore Negro League held their games over weekends and on holidays - when African-American fans were more able to come in from Baltimore and DC.
Enough background. Our ESBL day trip begins in sunny Sudlersville, Maryland - about 30 miles northeast of the Chesapeake Bay Bridge. This is the hometown of Hall of Famer Jimmie Foxx, nine-time all-star for the Philadelphia Athletics and Boston Red Sox in the 1920s and 30s. Prior to his major league debut at age 17, he batted .296 for the Easton Farmers. To honor the prolific home run hitter, Sudlersville erected a statue in the center of town. Not far from it, a small train depot was converted into a museum of the storied sluggers baseball career. Sadly, Foxx lost much of his hometown's goodwill after his playing days were over. Misinvested savings and health problems rendered the former great broke. He took up drinking and developed a reputation as a grouch. In 1952, he was hired as the manager of the Fort Wayne Daisies of the All-American Girls Professional League. Tom Hanks' character in A League of Their Own was partially based on Foxx.
Jimmie Foxx was discovered by another Hall of Famer, Eastern Shore native Frank "Home Run" Baker. Baker's formidable career as a player was wrapping up, while his young prodigy was just starting to make a name for himself at Sudlersville High School. In 1924, Baker returned home as player-manager of the Farmers. He invited Foxx to try out for the team and by the end of the season had sold the rising star's contract to his former employer, Connie Mack of the A's. Baker grew up in the nearby town of Trappe, 45 miles south of Sudlersville. His minor league years pre-dated the formation of the league, but he did do a couple of stints for semi-professional teams in Ridgley and Cambridge (both on the peninsula) - choosing to stay close to home until he was a little older. He is remembered in Trappe by a baseball park that bears his name. 
On the way down from Sudlersville to Trappe, you pass right through Easton - a town that fielded a team through 14 of the league's 16 seasons. There aren't any markers or memorials of the long-deceased league here, but their baseball spirit is still alive and well. For the past few decades, the focus has been on youth leagues. It was in Easton, in 1971, that former White Sox owner Bill Veeck caught his first glimpse of a 12 year old little league player named Harold Baines. Six years later, the White Sox drafted Baines in the first round. In his 20-year career, Baines put up stats considered just slightly shy of being Hall of Fame-worthy. His uniform number has since been retired by the White Sox, and there is a statue of his likeness at the White Sox' current stadium. In 1957, Harold Baines' father, Linwood Baines, played one town over for the Saint Michaels Red Sox of the Eastern Shore Negro League.
From Trappe, you are about 40 miles from Salisbury, Maryland - home of the Delmarva Shorebirds (Class A affiliate of the Orioles). The team's arrival in 1996 marked the return of minor league baseball to the Eastern Shore for the first time in 47 years. The Shorebirds play their home games at Perdue Stadium, which is also the location of the Eastern Shore League Hall of Fame and Museum (check website for hours). A visit to the museum will help you understand the regional baseball culture that produced great players like Foxx, Baker, and Baines, as well as other notable talent such as Mickey Cochrane, Red Ruffing, Mickey Vernon, and Don Zimmer, who all passed through on their way up the bigs. 
And we can't forget about Bill "Swish" Nicholson. He never played in the ESBL, but he grew up surrounded by it as a native of Chestertown, Maryland. In 1944 he became only the fourth player in MLB history to receive an intentional walk with the bases loaded. The fifth would not come until over 50 years later, in the person of Barry Bonds. It's said that Nicholson never watched a major league game until he played in one. The five-time all-star finished his MLB career with 235 home runs. There's a statue of Swish outside the visitors' center in Chestertown, which is about 15 miles west of Sudlersville.
All photos by Danial Orange, except 4 & 5: 1. signage in Sudlersville, MD alerts visitors to its most famous native son; 2. Jimmie Foxx statue in Sudlersville; 3. the sign at the entrance of Home Run Baker Park in Trappe, MD; 4. Baines' 1985 Topps card; 5. logo for the ESBL Hall of Fame and Museum; 6. Swish Nicholson statue in Chestertown, MD.
