Florida Big Bend High School Softball Players to Watch for in 2026

A trio of Chiles and Liberty County players headline this group of outstanding players to watch for this spring.

Chilles' Anna Kate Barber is a Player to Watch for the upcoming Florida high school softball season. / Anna Kate Barber

With the high school softball season set to begin here in the Sunshine State in February, it is time to turn our attention to some of the key returning players in the Big Bend region of Florida.

Chiles and Liberty County each had terrific 2025 campaigns, and each team returns a nucleus of players that have proven to be some of the best in all of northern Florida. If each of these players can replicate what they did last season, Chiles and Liberty County should be in the thick of the race for the state championship.

Meanwhile, Wakulla returns one of the top catches in the state from a season ago, and when it is all said and done, she might be the MVP in terms of what she means to her team beyond the stats.

Madison County returns one of the top hitters in terms of batting average from last season, and they also bring back one of the top pitchers as well.

Along with Madison County, North Florida Christian and St. John Paul II also return their ace which will be pivotal this season.

Lastly, Leon returns a talented offensive player who is also looking to improve as a pitcher this season.

Here are the 12 players to watch for in 2026:

Mia Hemenway, Chiles

As a freshman, Hemenway proved herself to be one of the most prolific hitters in the entire Southeast. She belted 17 home runs which was the most in Florida and finished with a .594 batting average. Hemenway also totaled 41 hits, 11 doubles, one triple and 52 RBIs on the season. Defensively, Hemenway also proved to be reliable as she fielded .969 in 64 total chances. If she builds upon the success from last season, we can be looking up at her in May as the best all-around player in the state.

Anna Kate Barber, Chiles

Barber was another super talented freshman for the Timberwolves in 2025 that is poised to have a big year in 2026. With what she showed and brought to the table last season, you could argue she was the team's MVP. Offensively, she batted .413 in 75 at-bats. Barber finished with 31 total hits, two home runs, four doubles, 29 RBIs and 20 runs scored. What sets her apart from most players in the region is her superb pitching ability. She went 18-3 last year with an ERA of 1.88 and struck out 142 batters. Barber will look to get her walk total down from 43, but she only allowed 29 earned runs on the season.

Kaitlyn Fagan, Chiles

Last season, Fagan's batting average was near the top for the Timberwolves as she finished with a .386 batting average in 83 at-bats. She totaled 32 total hits, one home run, nine doubles, 24 RBIs and 27 runs scored. When she got on base, Fagan made the defense pay as she stole 11 bases in as many attempts. Lastly, while in the field, her fielding percentage finished at .978 with 46 total chances.

Cha'miya Williams, Liberty County

Along with Hemenway, Williams was one of the top hitters in the region last year as she finished with a .516 batting average. She totaled 47 hits, eight home runs, five triples, 21 doubles, 47 RBIs and scored 47 runs. Williams was also dangerous on the base paths as she stole 22 bases last season. Lastly, her pitching prowess was also one of the best in the Big Bend. She finished with a 15-3 record and an ERA of 1.19. She finished with 144 strikeouts and only surrended 20 earned runs.

Taylor Kincaid, Liberty County

As we enter 2026, Kincaid will look to further build upon her .459 batting average from last season. She finished with 39 total hits, five home runs, 10 doubles, 27 RBIs and 28 runs scored in 85 at-bats. Like Williams, Kincaid was also always looking to steal as she finished 2025 with 12 steals. In the field, she hopes to improve on her .900 fielding percentage from last season. However, you shouldn't let that fool you as four games skewed that average. For most of the season, she was consistent on defense as she had 15 perfect games defensively.

Mackenzie Walker, Liberty County

As she enters her senior season, Walker is looking to take that next step to improve upon herself as a leader and teammate. Offensively, she batted .432 with 35 total hits, five home runs, two triples, 10 doubles, 29 RBIs and 37 runs scored. One thing, that makes Liberty County dangerous this season is what they do once they get on base. Like Williams and Kincaid, Walker was prolific on the base paths last season as she tallied 13 stolen bases.

Cylie Long, Wakulla

In 2025, Long might have been the most important player to her team for any school in the Big Bend region. She batted .494 with 43 total hits, nine home runs, two triples, 10 doubles, 31 RBIs and 18 runs scored. She patient at the plate and only struck out seven times in 87 at-bats. Defensively, she fielded .985 with 191 putouts in 200 total chances.

Skylar Young, North Florida Christian

Young is another player that returns this season who is dangerous every time she steps up to the plate. Last season, Young batted .421 with 32 hits, five home runs, two triples, eight doubles, 30 RBIs and 33 runs scored. She also finished with 19 stolen bases in 2025. Young also returns as one of the top pitchers in the region this season. In 2025, she finished with a 10-3 record and an ERA of 2.18. Young struck out 79 batters, walked 21 batters and allowed 26 earned runs.

Anna-Kayte Smith, Madison County

Madison County is another team in the region that returns a handful of players to watch for this season, and Anna-Kayte Smith is one of those players. In 2025, she batted .435 with 30 hits, five home runs, three triples, seven doubles, 28 RBIs and 15 runs scored. Defensively, she finished with a .970 fielding percentage with 91 putouts in 100 total chances.

Alden Bass, Madison County

In 2025, Bass was a nightmare in the pitcher's circle for opposing offenses. She finished 15-1 with an ERA of 1.27, struck out 165 batters and allowed only 20 earned runs. Offensively, she batted .308 with 20 total hits, three home runs, one triple, six doubles, 15 RBIs and scored 22 runs. Bass also stole nine bases on the year.

Amanda Thompson, St. John Paul II

Last season, Thompson batted .397 with 23 hits, five home runs, two triples, six doubles, 18 RBIs and 23 runs scored. As a pitcher, she finished with an ERA of 3.13, struck out 211 batters and allowed 51 earned runs in 114 innings of work.

Taylor Winfield, Leon

Winfield is another player who returns this season that batted over .400 in 2025. She batted .429 with 24 hits, one home run, one triple, five doubles, 13 RBIs and 29 runs scored. Winfield also tallied 19 stolen bases in 2025. From the circle, she went 4-1 with a 5.01 ERA and 58 strikeouts.