Beyond the Primaries: The 2026 Maryland County Executive Races That Actually Matter
By Barry O’Connell | The Maryland Wire
In Maryland politics, there’s a persistent myth that once the June primary wraps up, the local general elections are just a victory lap. For large swaths of the state—like Montgomery County, where Will Jawando is effectively measuring the drapes, or Prince George's—that’s true. Winning the Democratic nomination is 95% of the battle.
But if you look across the rest of the map, a handful of County Executive races this fall aren't anywhere close to decided. Suburban pushback, administrative infighting, and local scandals have turned several key jurisdictions into genuine battlegrounds.
Here is a clear-eyed breakdown of where the general election fights actually stand and why you shouldn't write off November just yet.
Frederick County: Toss-Up
The Matchup: Jessica Fitzwater (D) vs. William "Will" Holtzinger (R)
If you talk to voters along the I-270 corridor, you get the sense that Frederick should be a comfortable "Lean Democratic" seat. But looking closely at the ground-level dynamics, this race is shaping up to be a true toss-up.
Jessica Fitzwater won the seat in 2022 by less than a thousand votes (50.4\% to 49.5\%). Since then, her tenure has run into significant friction, particularly over rapid growth, tax reassessments, and the sprawling data center developments pushing into the county. The data center issue in particular has severed standard party lines: Fitzwater is taking heat not just from conservative property owners, but from environmentalists and anti-growth Democrats who feel local resident concerns are being secondary to tech infrastructure projects.
Enter Will Holtzinger, the former long-serving Mayor of Frederick who comfortably won the GOP primary. Holtzinger isn't a nationalized firebrand; he’s a known quantity with cross-party appeal from his years in city hall. If Holtzinger can unite traditional Republicans while picking off disillusioned Democrats frustrated by data centers and fiscal pressure, Fitzwater is in for the fight of her political career.
Wicomico County: Lean Republican / Wildcard
The Matchup: Julie Giordano (R) vs. Ernest Davis (D)
Down on the Eastern Shore, Wicomico is structurally a Republican-leaning county, but local political dynamics are making this a volatile contest.
Incumbent Republican Julie Giordano beat Democrat Ernest Davis in 2022, but her time in office has been marked by persistent friction with the County Council, contentious budget spats, and personal controversies that keep local political circles humming. The chatter surrounding personal conduct and leaked photos might sound like high school drama to outside observers, but on the Eastern Shore—where local church networks and traditional social conservatism hold real weight—personal character issues can move votes.
Ernest Davis, a former county councilman, has a solid institutional base and a clear path if enough conservative voters decide to stay home out of fatigue. Under normal conditions, Wicomico stays red, but if conservative voters sour on the incumbent, this becomes a genuine upset candidate.
Anne Arundel County: Lean Democratic / Competitive
The Matchup: Allison Pickard (D) vs. Dave Crawford (R)
Anne Arundel remains Maryland’s classic bellwether county. With Democrat Steuart Pittman term-limited, County Councilmember Allison Pickard secured the nomination after winning a competitive multi-way primary.
Pickard enters the general election with a distinct fundraising advantage and strong name recognition. However, her Republican opponent, volunteer fire chief Dave Crawford, presents a direct, law-and-order, community-first message that resonates well in South County, Pasadena, and Severna Park.
While national and state trends give Democrats the edge here, Anne Arundel voters routinely split their tickets on local tax, education, and public safety issues. It is Pickard’s race to lose, but it is far from a non-competitive venue.
Baltimore County: Likely Democratic
The Matchup: Julian Jones (D) vs. Patrick Dyer (R)
With Johnny Olszewski stepping down, Councilman Julian Jones won the Democratic primary after fending off Councilman Izzy Patoka.
Jones, a former career firefighter and division chief, carries a strong resume on public safety and labor. Baltimore County’s voter registration advantage makes Jones a heavy favorite against Republican Patrick Dyer. Unless Jones makes a massive unforced error, the structural math overwhelmingly favors the Democrats here. Still, conservative pockets in Dundalk, Essex, and Northern Baltimore County mean the GOP candidate will test Jones's margins on crime and county spending.
The Big Picture
While statewide headlines naturally focus on federal or gubernatorial movement, local county executives control zoning, local tax rates, and school budgets. If you’re looking for where the real general election drama lies this fall, keep your eyes on the data center fights in Frederick and the voter turn
out dynamics in Wicomico.
Now give us the skinny on Calvert and the MAGA candidates Grasso and Scaggs…