Turning 64? Here's Your 12-Month Medicare Planning Timeline

By Marc Gilman

📞 Call (800) 927-9326 or (603) 493-1394 | ✉️

If you’re turning 64 this year in Bedford, New Hampshire — or anywhere in Hillsborough County or New Hampshire or anywhere else actually — Medicare is closer than it feels. Twelve months goes faster than you’d expect, and the decisions you’ll face at 65 are significant enough that showing up prepared makes a real difference.

The good news: you don’t need to figure everything out today. But you do need to start. This timeline walks you through exactly what to do and when — month by month — so that by the time your Initial Enrollment Period opens, you’re making an informed decision rather than a rushed one.

Key Takeaways

Your Initial Enrollment Period (IEP) opens 3 months before your 65th birthday month. By the time it opens, you want your research done — not started.
If you’re contributing to an HSA, you may need to stop contributions 6 months before Medicare begins to avoid IRS tax penalties. This catches many people off guard.
Whether it’s safe to delay Part B depends entirely on your employer’s size — not just whether you have coverage.
New Hampshire has its own Medigap guaranteed-issue rules that differ from the federal standard. What’s true in Arizona or Florida may not apply here.
A local Bedford Medicare agent reviews all of this with you at no cost — and can tell you honestly whether your best option is something they can’t sell.

Your 12-Month Medicare Planning Timeline

12 Months Out — Understand the Landscape

What to do this month:

At 12 months out, your only job is to build a working understanding of how Medicare is structured. You don’t need to choose anything yet — but knowing the framework makes every conversation and decision that follows much cleaner.

Start here:

Understand the four parts. Part A covers hospital stays. Part B covers medical care (doctor visits, outpatient services). Part C (Medicare Advantage) bundles A and B into one private plan. Part D covers prescription drugs.
Know your two main coverage paths. You’ll eventually choose between Original Medicare (Parts A and B) plus a Medicare Supplement and Part D — or Medicare Advantage, which replaces Original Medicare with a private plan that usually includes drug coverage.
Find out if you’re automatically enrolled. If you’re already receiving Social Security benefits, you’ll be enrolled in Parts A and B automatically when you turn 65. If you’re not receiving Social Security, you’ll need to sign up actively.
Create your Medicare.gov account at medicare.gov. Your record of Medicare-covered earnings is there, and it’s useful to verify now.

9–10 Months Out — Understand Your Current Coverage

What to do this month:

Before you can make a smart Medicare decision, you need to know what you’re currently working with.

Review your current health insurance. Whether it’s employer coverage, a spouse’s plan, COBRA, union coverage, or a marketplace plan — understand what it covers and what it costs.
Ask your HR department whether your employer has 20 or more employees. This is the key rule for delaying Part B safely. If your employer has 20+ employees, Medicare becomes secondary to your employer plan and you can delay Part B without penalty. If your employer has fewer than 20 employees, Medicare becomes your primary coverage at 65 — whether you enroll or not. Getting this wrong is one of the most expensive Medicare mistakes we see.
Check your Social Security record at ssa.gov. Review your earnings history and estimated benefit amounts.
If you have an HSA (Health Savings Account): Note your 65th birthday carefully. <cite index=”33-1″>When you enroll in any form of Medicare, neither you nor your employer should continue contributing to your HSA.</cite> And because <cite index=”34-1″>when you sign up for Medicare after age 65, premium-free Part A is backdated up to six months — and any HSA contributions made during that retroactive period become excess contributions subject to tax penalties</cite> — you may need to stop HSA contributions 6 months before you plan to enroll, not just on the day coverage starts. Talk to your tax advisor or call us — the timing here matters.

7–8 Months Out — Build Your Personal Medicare Profile

What to do this month:

This is the research phase. The information you gather here drives every plan comparison you do later.

List every prescription medication you currently take — drug name, dosage, and how often you take it. This is your Part D comparison list.
List your current doctors and specialists — primary care, cardiologist, orthopedist, anyone you see regularly. You’ll use this list to check provider networks.
Identify your preferred hospitals and health systems in the Manchester–Bedford area. Elliot Health System, HCA Healthcare/CMC, and Dartmouth Health are the major regional systems — knowing which ones matter to you helps narrow plan choices significantly.
Check whether each of your doctors accepts Medicare. Most do, but it’s worth verifying before you assume.
Estimate your typical year in healthcare. How many specialist visits, procedures, or hospital stays have you had over the past few years? This helps frame the Medigap vs. Medicare Advantage decision honestly.

5–6 Months Out — Learn Your Coverage Options in Detail

What to do this month:

Now that you understand the basics and have your personal profile built, it’s time to go deeper on the actual choices you’ll face.

Medicare Advantage vs. Original Medicare + Medigap:

This is the biggest decision you’ll make at 65, and it’s worth understanding the real trade-offs rather than just the premiums.

Original Medicare + Medigap lets you see any provider in the country who accepts Medicare — no referrals, no network, no prior authorization. Medigap plans fill the gaps Original Medicare leaves, including the uncapped 20% Part B coinsurance. Premiums are generally higher, but costs are highly predictable. In New Hampshire, Medigap has its own guaranteed-issue rules that work differently from the federal standard — this is one area where a local NH agent genuinely matters.

Medicare Advantage plans replace Original Medicare with a private plan that usually has lower premiums, often $0, but comes with defined networks, prior authorization requirements, and plan-specific out-of-pocket maximums. Carrier availability in Hillsborough County shifted significantly in 2026 — several carriers pulled back or exited the NH market — which makes local plan-by-plan comparison more important than it’s been in years.

Part D drug coverage:

Whether you choose Original Medicare or Medicare Advantage, evaluate how your medications are covered. Compare formularies based on the medication list you built at 7–8 months out. A plan with a lower premium but a higher tier for one of your critical medications can easily cost you more over the year.

Other coverage to consider at 64:

At 64, you’re still insurable. By the time you’re enrolled in Medicare, some of these windows close or become significantly more expensive:

Life insurance — if you still have people depending on your income or have an estate planning need, 64 is a better year to act than 65 or 66.
Long-term care (LTC) coverage — the likelihood of needing some form of long-term care increases significantly with age, and LTC premiums rise sharply after 65. A policy or a life insurance policy with an LTC rider is far more accessible now than it will be at 70.
Hospital Indemnity Plan (HIP) and Cancer, Heart Attack & Stroke (CHAS) coverage — if you’re considering Medicare Advantage, these supplemental plans provide cash benefits that can offset the out-of-pocket exposure that comes with an Advantage plan.

3 Months Out — Your Initial Enrollment Period Opens

Your IEP opens 3 months before your birthday month. This is when you can take action.

By this point, your research should be done. The IEP phase is for deciding and enrolling — not starting from scratch.

Evaluate specific Medicare Advantage plans available in Hillsborough County based on your doctor list, medication list, and preferred hospitals.
Compare Medicare Supplement plans offered in New Hampshire across multiple carriers. Medigap plan benefits are standardized by letter (Plan G, Plan N, etc.), so the comparison is primarily on premium and carrier rating.
Compare Part D plans on Medicare.gov‘s Plan Finder, entering your specific medications for an apples-to-apples cost comparison.
Contact your HR department to notify them of your Medicare enrollment intent and understand how your employer plan coordinates with Medicare during the transition.
Decide whether to keep employer coverage, drop it, or coordinate both. In some cases, keeping employer coverage alongside Medicare Part A (while delaying Part B) makes financial sense. In others, Medicare is the better primary coverage from day one.
Set up automatic premium payment through your Social Security benefit or bank account to avoid gaps in coverage.

Your Birthday Month — Coverage Begins

Enrollment timing during the IEP affects your coverage effective date:

When You Enroll and Your Part B Effective Date

After Enrollment — Continue Reviewing

Medicare isn’t a set-it-and-forget-it decision.

September: Medicare Advantage and Part D plans send Annual Notices of Change (ANOC). Read yours. Premiums, formularies, and networks change every year — your plan may no longer be the right fit even if it was perfect when you enrolled.
October 15th–December 7th: Annual Enrollment Period. You can switch Medicare Advantage or Part D plans for the following year.
Any time: If you move, lose other coverage, or experience a qualifying life event, you may have a Special Enrollment Period.
Annually: Review your Part D plan against your current medication list. Drugs get moved between formulary tiers; a plan that was cost-effective one year may not be the next.

Why Starting at 64 Is the Right Move

The clients I’ve worked with who had the smoothest Medicare transitions at 65 started the conversation at 64. Not because the process is complicated — but because the decisions are interconnected. The HSA timing question affects your tax filing. The employer-size question affects whether you can delay Part B at all. The Medigap vs. Advantage decision affects your choices at every Annual Enrollment Period going forward. None of these questions should be answered under deadline pressure.

At Gilman Agency, a Medicare planning conversation at 64 costs you nothing. We’re not enrolling you in anything — we’re building your roadmap so that when your IEP opens, you’re ready to act.

Frequently Asked Questions

When should I start planning for Medicare if I live in Bedford, NH? Ideally at 64 — 12 months before your IEP opens. The research, coverage comparisons, and logistical steps (HSA timing, employer coordination, provider verification) all benefit from time. Waiting until your birthday month means making major decisions in a compressed window, often under pressure.

Do I have to enroll in Medicare at 65 if I still have employer coverage in Hillsborough County? Not necessarily — but it depends on your employer’s size. If your employer has 20 or more employees, you can typically delay Part B without penalty while your employer plan is active. If your employer has fewer than 20 employees, Medicare becomes your primary coverage at 65 whether you enroll or not, and delaying Part B creates gaps. This is a critical distinction that’s easy to get wrong.

Can I keep contributing to my HSA after I turn 65? Only if you haven’t enrolled in any part of Medicare. Once you enroll — including premium-free Part A — your HSA contribution eligibility ends. Because Part A can be applied retroactively up to six months when you enroll after 65, most people are advised to stop contributions six months before they plan to enroll to avoid IRS penalties on excess contributions. Talk to your tax advisor about your specific timeline.

Is a Medicare planning consultation free in Bedford, NH? Yes. Working with a licensed Medicare agent costs nothing. Whether you’re enrolling in a plan or just doing early research, there’s no charge to you.

Serving All of Hillsborough County and All of New Hampshire

Gilman Agency helps residents turning 64 and 65 throughout Hillsborough County plan and navigate their Medicare enrollment — including Bedford, Manchester, Nashua, Merrimack, Goffstown, Amherst, Milford, Hudson, Hollis, Litchfield, Pelham, Brookline, New Boston, Weare, Antrim, Bennington, Deering, Francestown, Greenfield, Greenville, Hancock, Hillsborough, Lyndeborough, Mason, Mont Vernon, New Ipswich, Peterborough, Sharon, Temple, Wilton, and Windsor.

If you’re turning 64 this year, now is the right time to start. Call (800) 927-9326 or (603) 493-1394, or email to schedule your no-cost Medicare planning conversation.

Turning 64? Here’s Your 12-Month Medicare Planning Timeline

Key Takeaways