Medicare 2026

Medicare at 65: Burlington guide to signing up on time

BURLINGTON, Vt. — If a 65th birthday is on your horizon, Medicare has already set aside a specific stretch of time for you to sign up. It's called the Initial Enrollment Period, and knowing how it works can save you from late penalties, gaps in coverage, and a lot of second-guessing.

Aging into Medicare: the enrollment window you don't want to miss

Here's what Burlington-area readers should understand before that birthday arrives.

What the Initial Enrollment Period actually is

Your Initial Enrollment Period (IEP) is a seven-month window built around the month you turn 65. It starts three months before your birthday month, includes your birthday month, and continues for three months after.

For example, if you turn 65 in June, your IEP runs from March 1 through September 30. During this window, you can enroll in Medicare Part A (hospital), Part B (medical), a Part D prescription drug plan, or a Medicare Advantage plan.

A helpful tip from CMS: if you sign up in the three months before your birthday month, your coverage typically starts on the first day of your birthday month. Sign up later in the window, and coverage begins the month after you enroll. That timing matters if you're planning around another insurance ending.

First steps to take before you turn 65

You don't have to figure this out in one sitting. A few practical starting points:

• Check whether you'll be auto-enrolled. If you're already receiving Social Security benefits, you'll usually be enrolled in Parts A and B automatically. If not, you'll need to sign up yourself through the Social Security Administration.
• Look at your current coverage. Do you have employer insurance, retiree coverage, VA benefits, or a spouse's plan? Some coverage works well alongside Medicare; other coverage should be replaced by it. This decision affects whether you should take Part B right away.
• Make a list of your prescriptions and preferred doctors. You'll want this handy when comparing Part D or Medicare Advantage options later.
• Understand the two main paths. After enrolling in Parts A and B (Original Medicare), most people either add a standalone Part D drug plan (often with a Medigap supplement) or choose a Medicare Advantage plan that bundles coverage. Each path has trade-offs.

What's available in the Burlington area

Burlington is in Chittenden County, where residents can compare the Medicare Advantage and Part D plans offered locally on Medicare.gov's Plan Finder. Plan availability, networks, and formularies are set at the county level, so what's offered in Chittenden County may differ from neighboring counties.

Rather than trying to memorize plan details, use the Plan Finder tool to enter your ZIP code, your medications, and your preferred pharmacies. It will show you what's available in your area without any sales pressure.

2026 and 2027 program facts worth knowing now

Even before you pick a specific plan, some Medicare rules apply across the board. Here's what to know for 2026 and 2027:

• Part D has a $2,100 out-of-pocket cap on covered prescription drugs. Once you hit it, you pay $0 for the rest of the calendar year on covered drugs.
• The Part D maximum deductible is $615 in 2026 and $700 in 2027 (plans may set it lower).
• The old "donut hole" coverage gap was eliminated in 2025. Part D now has three phases: deductible, initial coverage, and catastrophic.
• The Medicare Prescription Payment Plan lets you spread drug costs into monthly payments rather than paying a large amount at the pharmacy counter. It's optional and free to opt into.
• IRMAA surcharges — higher Part B and Part D premiums for higher-income enrollees — start above $109,000 in income for a single filer in 2026.

Missing the window: why it matters

If you don't sign up during your IEP and don't qualify for a Special Enrollment Period (for example, because you had qualifying job-based coverage), you may face:

• A Part B late enrollment penalty that gets added to your premium for as long as you have Medicare.
• A Part D late enrollment penalty if you go 63 days or more without creditable drug coverage.
• A wait until the General Enrollment Period (January 1 – March 31) to sign up, with coverage beginning the month after enrollment.

These penalties are permanent, which is why the seven-month window gets so much attention.

Other enrollment periods to keep on your radar

Once you're in Medicare, two other windows come up each year:

• Annual Enrollment Period: October 15 – December 7. This is when anyone with Medicare can review and change their Part D or Medicare Advantage coverage for the following year.
• Medicare Advantage Open Enrollment: January 1 – March 31. If you're already in a Medicare Advantage plan, you get one chance during this window to switch to a different Advantage plan or return to Original Medicare.