Medicare Advantage

Wilmington Medicare 2027: Key Dates & AEP

WILMINGTON, Del. — If you live in Wilmington and are sorting through Medicare choices for 2027, the calendar matters as much as the plan list. New Castle County had 36 Medicare Advantage plans available for 2026, according to the CMS Medicare Plan Finder; the 2027 lineup is in each plan's Annual Notice of Change and on Medicare.gov's Plan Finder. Knowing which enrollment window you're in — and when it closes — is what keeps those options open to you.

Why the dates matter more than the plan count

Wilmington sits in New Castle County, where 36 Medicare Advantage plans from 8 carriers were on the 2026 landscape. The 2027 lineup is detailed in each plan's Annual Notice of Change and on Medicare.gov's Plan Finder. It's typically a wide field — but you can only act on it during the windows Medicare sets. Miss a window and, in most cases, your current coverage rides for another year.

That's why this guide walks through the deadlines first. The plan count is the "what." The calendar is the "when," and "when" is what most Wilmington readers get tripped up on.

The Annual Enrollment Period: Oct. 15 – Dec. 7

This is the big one. Between Oct. 15 and Dec. 7 each year, anyone with Medicare can:

• Switch from Original Medicare to a Medicare Advantage plan, or the other way around.
• Change from one Medicare Advantage plan to another.
• Join, drop, or switch a Part D prescription drug plan.

Any change you make during this window takes effect Jan. 1. If you do nothing, your current plan generally renews automatically — but the details (formulary, network, cost-sharing) can shift year to year. Every fall, your plan sends an Annual Notice of Change. Read it before Dec. 7, not after.

Note for New Castle County: Delaware has 10 stand-alone Part D plans for 2026, sold statewide, and residents of the county can join any of them. The 2027 lineup is on Medicare.gov's Plan Finder. If you rely on Original Medicare plus a stand-alone drug plan, double-check what's available on medicare.gov before the Dec. 7 deadline — the Plan Finder is the authoritative source.

The Medicare Advantage Open Enrollment Period: Jan. 1 – March 31

If you're enrolled in a Medicare Advantage plan on Jan. 1, you get one more shot. Between Jan. 1 and March 31, you can:

• Switch to a different Medicare Advantage plan.
• Drop your Advantage plan and go back to Original Medicare (and add a stand-alone Part D plan).

You can only use this window once, and it doesn't apply if you're in Original Medicare on Jan. 1. It's meant as a safety valve — a chance to correct a choice that isn't working — not a second full shopping period.

Turning 65 or new to Medicare? Your own window

If you're aging in, your Initial Enrollment Period is a seven-month window: the three months before your 65th birthday month, your birthday month, and the three months after. Signing up during the three months before your birthday month usually means coverage starts the month you turn 65.

Miss it, and you may face late-enrollment penalties for Part B and Part D that stick with you for as long as you have Medicare. That's the costliest deadline mistake in the whole system, so don't let it slip past.

Special Enrollment Periods: when life changes the calendar

Some life events open a Special Enrollment Period outside the normal windows — moving out of your plan's service area, losing employer coverage, qualifying for Extra Help or Medicaid, or moving into or out of a nursing facility, among others. The rules and timelines vary by event, so confirm with 1-800-MEDICARE or your local SHIP before you assume you qualify.

What 2027 changes mean for your timing

Two program-level updates are worth noting as you plan:

• The Part D out-of-pocket cap is $2,100 in 2026 and $2,400 in 2027. Once your drug spending hits that ceiling, you pay nothing for covered Part D drugs the rest of the year.
• The Medicare Prescription Payment Plan lets you spread Part D costs across the calendar year in monthly installments instead of paying at the pharmacy counter. You can opt in for 2027 — ask your drug plan how.

Neither of these changes the enrollment dates, but they may change the math on whether your current plan still fits.

How to decide, step by step

1. Pull out your Annual Notice of Change and read what's different for 2027. 2. List your prescriptions, your doctors, and any hospitals you want covered. 3. Go to medicare.gov and use the Plan Finder to compare New Castle County options side by side. 4. If you want free, unbiased help, call Delaware's SHIP (the Delaware Medicare Assistance Bureau, or DMAB) at 1-800-336-9500. 5. Make your choice before Dec. 7, 2026 for a Jan. 1, 2027 start.