Two insurance windows land on Talbot County this fall, six weeks apart, and they are easy to mix up. This sheet is a calendar and a price note, not a plan recommendation.

Medicare Open Enrollment runs Oct. 15 through Dec. 7. That is the period to join, switch, or drop a Medicare Advantage or Part D plan, with coverage starting Jan. 1.

Maryland Health Connection open enrollment runs Nov. 1 through Jan. 15. Enroll by Dec. 31 for coverage that begins Jan. 1. That is the marketplace — a different program, different rules, different deadline.

Prices are moving again. Maryland carriers requested an average individual-market increase of 13.7 percent for 2027, ranging from 12 to 14.6 percent. Small-group requests averaged 13.1 percent. Insurance Commissioner Marie Grant linked the increases, for the second consecutive year, to the loss of enhanced federal tax credits that Congress did not extend. The Maryland Insurance Administration held a hearing in July and expects to issue decisions in September. Until that order lands, 13.7 percent is a request, not an approved rate.

Why the county feels it. Talbot skews older and self-employed — watermen, farmers, trades, hospitality. That is the population buying unsubsidized individual coverage, and a double-digit increase is not abstract for households writing the full premium.

Free help, on the record. The State Health Insurance Assistance Program serves Talbot through Upper Shore Aging. Christina Kinnamon is program coordinator at 410-822-2869. SHIP counseling is free and unbiased. It covers Parts A through D, Medigap, claims and appeals, and referrals to Medicare Savings Programs and the Part D Low Income Subsidy. SHIP is not seniors-only: it serves Medicare beneficiaries of any age, including people under 65 who qualify through disability.

The Talbot County Health Department also offers health-insurance application assistance and a free adult vaccine program for uninsured and underinsured residents at 410-819-5673.

Book before the first week of October if you want a counselor rather than a mailbox full of advertising. This is a dated health sheet, not a diagnosis.