It's August on Maryland's Eastern Shore, and local high school football teams are out on the field preparing for the beginning of their new season in a few weeks. And the 2026 season looks to be another exciting one to keep an eye on in the Bayside South.
A lot happened on the gridiron in the Bayside South in 2025. Stephen Decatur won a third Bayside Conference Championship. Wi-Hi made it to the MPSSAA State Semifinals. Washington won their first regular season game since 2019 and their first playoff game in 22 years. And individual stars made big impressions throughout the year, like Parkside's Tavian Dashiell, who was named the Class 2A Player of the Year by Sports Illustrated.
For football fans looking ahead towards what's coming in 2026, they'll have their eyes on this season's calendar as they look for the biggest games to watch during this year. And if this season is anything like last year, there will be plenty of big games to keep an eye on when things kick off in September.
Here are some of the top Bayside South football games to watch this upcoming season:
Stephen Decatur at Wicomico
Sept. 11 | 4 p.m.
An early season matchup between the two best teams from last year in the Bayside South, Stephen Decatur is set to head to Salisbury to face Wi-Hi on Sept. 11.
Both teams will look back on the 2025 season as a success, as Decatur won their third consecutive Bayside title, while Wi-Hi made a trip to the MPSSAA 2A State Semifinals for the first time in two decades. And their matchup last season was a consequential one, as Wi-Hi became the first team in three years to defeat the Seahawks after they had embarked on two consecutive undefeated state championship seasons.
Some familiar faces and key contributors from both teams have moved on since last year, like Decatur's Johnny Hobgood, Wi-Hi's Kevin Thomas, and Decatur's head coach Jake Coleman. But this should still be a big early season games that is worth circling on the calendar for local high school football fans.
Parkside vs. James M. Bennett
Sept. 17 | 6 p.m.
A Bayside South staple throughout the local high school athletic year is the three-way rivalry between Salisbury high school's Parkside, James M. Bennett and Wicomico. As they battle it out for bragging rights and the right to call themselves City Champions, matchups between the three teams are always as fierce as you would expect from rivals that are in such close proximity to one another.
As usual, there will be three games between those three teams this season, and the first is set to take place during the third week of the season, as the Parkside Rams and Bennett Clippers go toe-to-toe at Wicomico County Stadium.
Recent matchups between these two teams have been down to the wire, with two of the last three decided by just one point. After losing in each of the previous two years, Parkside was able to get revenge last year with a victory. The Rams and Clippers seem to bring the best out of each other when they meet on the field, and fans of both teams will be hoping that remains the same when they meet on Sept. 17.
Snow Hill at Washington
Sept. 25 | 6 p.m.
Last year was a historic year for the Washington Jaguars. After multiple consecutive winless seasons, they won their first game since 2019 when they defeated North East in early September. And it did not stop there for the Jaguars, as they managed to finish the season with a winning record, culminating in their first playoff win in 22 years.
That playoff win came against their Bayside South rivals Snow Hill, the only other Class 1A team in the Bayside South alongside Washington. Matchups between these two are always important not just for bragging rights, but also for any potential postseason ramifications.
Last year's victory over Snow Hill was a major one for the Washington Jaguars, as they look to build on what they achieved in 2025. And for Snow Hill, they'll certainly be looking for revenge when these two face off in late September.
Easton at Stephen Decatur
Oct. 15 | 6 p.m.
A matchup between the defending conference champions, and one of the teams that can potentially take their crown this season, Stephen Decatur is set to host Easton in late season matchup this year.
In August, it is too far out to fully predict where things will be once the season is in full swing in the middle of October. But as the defending Bayside champions, Decatur will certainly hope to be one of the main teams in the mix at the top of the Bayside when this game comes up on the schedule. And their visiting opponents Easton will certainly hope to be there at the top as well. The Warriors went 8-3 last year, and have added some key transfers to their team to bolster their chances in 2026.
In back-to-back weeks, Easton will face Decatur and Wi-Hi, the two most successful Bayside Conference teams last season. Bayside fans will hope that these late season matchups provide tons of fireworks before the postseason begins.
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This article originally appeared on Salisbury Daily Times: Top Bayside South high school football games to watch in 2026