Trusted accounting. Thoughtful advice. Local expertise.
Serving individuals, small businesses, and nonprofits on Maryland’s Upper Eastern Shore.
Anthony Judge and Ware is a full‑service accounting firm based in Chestertown, Maryland, providing tax, accounting, and advisory services with clarity, care, and decades of experience. We work closely with individuals, business owners, and nonprofit organizations to deliver practical solutions that support sound financial decisions—today and for the long term.
A steady partner for complex financial needs
For generations, clients have relied on Anthony Judge and Ware for accurate work, responsive service, and straightforward guidance. Our approach is personal and proactive: we take time to understand your goals, anticipate challenges, and tailor our services to fit your situation—not the other way around.
Licensed in Maryland, our team offers a broad range of services backed by deep technical knowledge and a strong commitment to client relationships.
Comprehensive Financial Services
Tax preparation and planning
Tax preparation for individuals, businesses, estates, trusts, private foundations, and nonprofits, paired with proactive planning to reduce tax liability and identify opportunities.
Business advisory services
Flexible support for small and growing organizations, including payroll, data processing, general ledger reconciliation, internal financial statements, budgeting, and financial analysis.
Accounting and bookkeeping
Accounting support with deep expertise in QuickBooks Desktop and QuickBooks Online, ensuring accurate records and clear financial insight.
Estate and Trust Planning
Estate and trust planning and tax preparation focused on asset protection, wealth preservation, and minimizing tax burdens for you and your heirs.
Payroll services
Live and after-the-fact payroll services, including federal and state tax deposits and all required monthly, quarterly, and annual filings.
Additional Services
Preparation of 1099s and Heavy Highway Vehicle Use Tax Returns (Form 2290).
Our clients can expect expertise informed by decades of tax practice and a tailored, client‑focused service. We believe effective accounting starts with listening. By understanding your priorities and challenges, we deliver guidance that is practical, compliant, and aligned with your goals.
We proudly serve:
Individuals and families
Small and mid‑sized businesses
Nonprofit organizations
Who we serve
Our Team
James Judge, CPA
Arraminta Ware, CPA
Michelle Pepper, EA
Ryan Ramsey, CPA
Catherine Gattens, staff accountant
Jessica Anthony, staff accountant
Molly Judge, payroll specialist
Laura Cruz, office manager
Our Location
Visit us at our office, located just off of Route 213 in Chestertown: 925 Gateway Drive, Chestertown Maryland, 21620