Working past 65 · Garfield County, Colorado · 2026

Working past 65 in Garfield County: your 2026 Medicare decision

If you're still working at 65 in Rifle, Glenwood Springs, Carbondale, or Parachute, you may be able to delay Medicare Part B without a penalty — or you may be one bad assumption away from paying most of a hospital bill yourself. The whole thing turns on a single number: how many people your employer has.

Bemis Insurance Data Desk

Reviewed by Trinity Bemis, Licensed Insurance Broker & Medicare Specialist (NPN 21424070) · Published 2026-08-12

The short answer

If you're 65 or older and covered by a group health plan through your own or your spouse's current job at an employer with 20 or more employees, that plan pays first, Medicare pays second, and you can generally wait to sign up for Part B until the job ends — with no late enrollment penalty. If the employer has fewer than 20 employees, Medicare pays first, and delaying Part B means the bill has no primary payer at all. Everything else in this article follows from that split. Two conditions have to hold: the coverage must come from current employment (not retiree coverage, not COBRA), and the headcount must clear 20. Get either wrong and the consequences are financial, permanent, and entirely avoidable. This is education, not advice — every rule below links to Medicare.gov, CMS, the IRS, or the Census Bureau.

Sources: Medicare.gov — Who pays first? · Medicare.gov — Working past 65.

Does my employer have 20 or more employees?

This is the question. Not "do I feel healthy," not "is my plan good," not "what does my neighbor do." Medicare's coordination-of-benefits rules — the Medicare Secondary Payer rules — hang almost entirely on employer size.

Medicare.gov's own decision tool asks it in exactly these words: "Does the employer providing your health insurance coverage have 20 or more employees (or is the employer part of a multi-employer group health plan where at least one company has 20 or more employees)?"

• Yes, 20 or more: "The group health plan pays first, and Medicare pays second." You can generally delay Part B without penalty while that coverage continues.
• No, fewer than 20: "Medicare pays first, and the group health plan pays second." You should enroll in Part A and Part B when you turn 65.

Three details that trip people up:

• Part-time employees count. The 20-employee test counts both full-time and part-time workers, not full-time equivalents.
• It's the employer, not the location. A four-person branch office of a 400-person company is a 400-employee employer for this purpose.
• Multi-employer plans can rescue you. If your small employer participates in a multi-employer or union plan where at least one participating company has 20 or more employees, the plan can still pay primary — though CMS allows those plans to request a small employer exception for their under-20 participants, which flips Medicare back to primary. That request is made by the plan, not by you, so you have to ask.

What this means practically: do not guess, and do not rely on what HR said to somebody else three years ago. Ask your benefits administrator two written questions — how many employees does the company have for Medicare Secondary Payer purposes, and does the plan pay primary or secondary for employees 65 and older? Medicare.gov's guidance is blunt about the stakes: "If you don't sign up for Part A and Part B, your job-based insurance might not cover the costs for services you get."

Sources: Medicare.gov — Who pays first? · CMS — Small Employer Exception (Medicare Secondary Payer) · Medicare.gov — Working past 65.

Why that question is a real problem in Garfield County

On a lot of Medicare websites the under-20 rule reads like a footnote. In Garfield County it's the main case.

The Census Bureau's County Business Patterns program counts business establishments and sorts them by how many people they employ. In 2022, Garfield County had 2,666 business establishments. Of those, 2,443 — about 92% — had fewer than 20 employees. More than that: 1,702 establishments, roughly 64% of the county's total, had fewer than five. Only 223 establishments in the entire county were in a size class of 20 or more.

Source: US Census Bureau — County Business Patterns — 2022 County Business Patterns, Garfield County, Colorado, all industries (NAICS 00), retrieved August 2026. The 250–499 size class is suppressed in the published county file for disclosure reasons, so the classes shown sum to slightly less than the 2,666 total.

One honest caveat, because it matters here. County Business Patterns counts establishments — physical locations — while Medicare's 20-employee test counts the employer's total workforce, across all its locations, using a rule based on employing 20 or more people on each working day in 20 or more calendar weeks of the current or preceding year. A small Glenwood Springs storefront belonging to a national chain is a big employer under Medicare's rules and a small establishment in this chart. So treat the figures above as what they are: a picture of how small the typical workplace is on this stretch of the I-70 corridor, not a headcount of your specific employer. That one you still have to ask about.

Even with that caveat, the direction is unmistakable. In a county built on contractors, ranch operations, restaurants, retail storefronts, professional practices, and self-employment, the odds that your employer clears 20 employees are meaningfully worse than they would be in a metro area — and the cost of assuming otherwise falls entirely on you.

And if you're self-employed? Medicare.gov puts self-employment in the "ask your insurance provider whether your coverage is employer group health plan coverage as defined by the IRS" bucket — and adds that if it isn't, you should sign up for Medicare when you turn 65 to avoid the Part B late enrollment penalty. An individual policy you bought yourself is not employer group coverage, no matter how good it is.

Sources: US Census Bureau — County Business Patterns · CMS — Small Employer Exception (Medicare Secondary Payer) · Medicare.gov — Working past 65.

Should I take Part A at 65 while I'm still working?

Usually yes — with one significant exception covered in the next section.

CMS reports that approximately 99% of Medicare beneficiaries pay no Part A premium, because they have at least 40 quarters of Medicare-covered employment as determined by Social Security. Medicare.gov's guidance follows from that: "Most people don't have to pay a premium for Part A (Hospital Insurance). So, you may want to sign up for Part A when you turn 65, even if you or your spouse are still working." Part A can sit alongside your employer plan and pick up hospital costs the group plan doesn't.

If you don't have 40 quarters, Part A is not free, and the arithmetic changes completely. In 2026:

• $311 a month if you (or your spouse) have 30 to 39 quarters of coverage — a $26 increase from 2025.
• $565 a month if you have fewer than 30 quarters — a $47 increase from 2025.

At those prices, buying Part A while you still have qualifying employer coverage is often the wrong move, and the Part A late enrollment penalty is unusually mild by Medicare standards — 10% for twice the number of years you delayed, not for life. For reference, the 2026 Part A inpatient hospital deductible is $1,736 per benefit period; we walk through how that interacts with observation status in our guide to hospital and rehab costs.

Sources: CMS — 2026 Medicare Parts A & B Premiums and Deductibles · Medicare.gov — When can I sign up for Medicare? · Medicare.gov — Avoid late enrollment penalties.

The Health Savings Account trap

If your employer plan is a high-deductible plan paired with a Health Savings Account, "just take the free Part A" becomes actively bad advice, and the reason is tax law rather than insurance law.

The IRS is unambiguous: beginning with the first month you are enrolled in Medicare, your HSA contribution limit is zero. That includes premium-free Part A. Contributions made during a month you were enrolled are excess contributions, subject to tax.

What makes this a trap rather than a simple rule is retroactivity. When you enroll in Medicare after 65 — or claim Social Security after 65, which enrolls you in Part A automatically — Part A can be backdated up to six months (never earlier than the month you turned 65). The IRS notes that people whose Medicare coverage is applied retroactively "cannot make contributions to the HSA for the period of retroactive coverage." You didn't feel enrolled during those months. The IRS says you were.

Hence Medicare.gov's plain instruction: "If you have a Health Savings Account (HSA), you and your employer should stop contributing to your HSA 6 months before you retire or apply for benefits from Social Security."

Three practical notes:

• You can keep spending HSA money after you enroll in Medicare, including on Medicare premiums and other qualified expenses. It's only new contributions that stop.
• Employer contributions count too — tell payroll, not just yourself.
• If you did over-contribute, the IRS allows you to withdraw the excess plus the earnings attributable to it, without penalty, if you do it by your return's due date including extensions. Talk to a tax professional; that part is outside what an insurance agency can advise on.

Sources: IRS — Publication 969, Health Savings Accounts and Other Tax-Favored Health Plans · Medicare.gov — Working past 65.

Who pays first, in one table

These are the published federal coordination-of-benefits rules. "Pays first" means the primary payer settles up to the limits of its coverage; the secondary payer only picks up costs the primary didn't cover.

Source: Medicare.gov — Who pays first?. One further warning from the same page worth repeating: if you're in an HMO or an employer PPO that pays first and you get services outside that plan's network, "it's possible that neither the plan nor Medicare will pay." In a service area where specialty care often means a drive to Grand Junction or Denver, call the plan before you go.

Sources: US Census Bureau — County Business Patterns · US Census Bureau — ACS 2019–2023, Table S2301 (Employment Status) · Medicare.gov — Working past 65 · Medicare.gov — Avoid late enrollment penalties.

How the 8-month Special Enrollment Period works

When qualifying employer coverage ends, Medicare gives you a Special Enrollment Period — and the details of when it starts and when coverage begins are where people lose months.

The window. Medicare.gov: "Once you stop working (or lose your health insurance, if that happens first) you have an 8-month Special Enrollment Period (SEP) when you can sign up for Medicare (or add Part B to existing Part A coverage). The SEP starts when you stop working (or lose insurance), even if you choose COBRA or other coverage that's not Medicare."

Read that last clause twice. The clock starts at the job, not at the coverage.

The timing. If you want Medicare to start the day your job coverage ends, don't wait until it ends. Medicare.gov: "If you want Medicare coverage to start when your job-based health insurance ends, you need to sign up for Part B the month before you or your spouse plan to retire. Your coverage will start the month after Social Security (or the Railroad Retirement Board) gets your completed forms."

The paperwork. Signing up through this SEP takes two forms, not one: the Part B application itself, plus — in Medicare.gov's words — "an extra form showing you had job-based health coverage while you or your spouse were working." That second form has to be completed by your employer. Start asking for it early; a small business in Rifle whose HR function is one person who also does payroll may take a few weeks to turn it around. Social Security handles the enrollment.

If you miss it. You fall to the General Enrollment Period, January 1 through March 31. Coverage starts the month after you sign up, which means a gap — and a Part B late enrollment penalty that stays with you.

Sources: Medicare.gov — Working past 65 · Medicare.gov — When can I sign up for Medicare? · SSA — Sign up for Part B only · Medicare.gov — COBRA coverage.

COBRA and retiree coverage are not "still working"

This is the most expensive misunderstanding in the whole subject, and it's an easy one to fall into, because COBRA feels like a continuation of your job's insurance. To Medicare, it isn't.

COBRA is coverage based on former employment. That has two consequences, both bad if you weren't expecting them:

1. It doesn't buy you time. Medicare.gov: "Don't wait until your COBRA coverage ends to sign up for Part B — COBRA coverage doesn't extend your limited time to sign up for Medicare." You get 8 months from the day the job ended, "whether or not you choose COBRA." Take 18 months of COBRA at 65 and you will spend ten of them out of the window entirely.
2. It doesn't pay first. Once you're 65 and Medicare-eligible, Medicare pays first even if you never enrolled. Medicare.gov's warning: "If you have COBRA and you're eligible for Medicare but not enrolled, COBRA may only pay for a small portion of the health care services you get, and you may have to pay most of the costs yourself. Contact your COBRA plan and ask what percent they pay."

Retiree coverage from a former employer behaves the same way. Medicare pays first; the retiree plan pays second. And Medicare.gov adds a sharper caution: retiree coverage "might not pay your medical costs during any period when you were eligible for Medicare but didn't sign up for it." Many retiree plans are designed on the assumption that you enrolled in both Part A and Part B — and they price and pay accordingly.

One narrow piece of good news: if your COBRA includes creditable prescription drug coverage, you do get a Special Enrollment Period to join a Medicare drug plan without a Part D penalty when the COBRA ends. That protection covers Part D. It does not cover Part B.

Two footnotes worth knowing locally. COBRA itself generally only applies to employers with 20 or more employees — which, given the establishment sizes above, leaves a lot of Garfield County workers outside it in the first place. Some states run "mini-COBRA" continuation laws for smaller employers; the Colorado Division of Insurance can tell you what applies to your situation.

Sources: Medicare.gov — COBRA coverage · Medicare.gov — Who pays first? · Colorado Division of Insurance — Senior health care & Medicare (SHIP).

What getting it wrong costs in 2026

Medicare's late enrollment penalties are not late fees. They're permanent premium surcharges, and they are indexed — they grow every year the underlying premium grows.

Part B: an extra 10% for each full 12-month period you could have signed up but didn't. Medicare.gov's published 2026 example works like this: someone who waited two full years without qualifying for a Special Enrollment Period owes a 20% penalty. That's $40.58 on top of the $202.90 standard premium, for a total Part B premium of $243.50 a month in 2026 — and Medicare.gov states plainly that it's charged "for as long as you have that type of coverage (for most people, that's a lifetime penalty)." We break down the mechanics further in our Part B late enrollment penalty guide.

Part D: an extra 1% for each uncovered month — 12% a year — calculated against the 2026 national base beneficiary premium of $38.99, and triggered by going 63 days or more without creditable drug coverage. It's added to whatever your drug plan charges, for as long as you have Medicare drug coverage, even if you switch plans.

The gap is its own cost. Missing the SEP means waiting for January–March and starting coverage the month after you sign up. Depending on when your job ended, that can be months with no primary payer at all — and in 2026 the Part A hospital deductible alone is $1,736 per benefit period.

Neither penalty applies if you genuinely qualified for a Special Enrollment Period. Which is why the paperwork proving your employer coverage matters as much as the coverage did.

Sources: Medicare.gov — Avoid late enrollment penalties · Medicare.gov — How much does Medicare drug coverage cost? · CMS — 2026 Medicare Parts A & B Premiums and Deductibles.

What about my prescription coverage?

Part D runs on a separate track from Part B, with its own test: creditable coverage. Medicare.gov: "As long as you have creditable prescription drug coverage, you can wait to join a Medicare drug plan or a Medicare Advantage Plan with drug coverage."

Creditable means the drug coverage is expected to pay, on average, at least as much as standard Medicare drug coverage. Your plan is required to tell you whether yours qualifies, and to send you that notice every year — usually in the fall, usually in an envelope that looks like junk mail. Keep it. You may need it when you eventually join a Medicare drug plan, and it's the document that proves you weren't uncovered.

The rule to remember is the 63-day rule: you won't pay the Part D late enrollment penalty as long as you don't go more than 63 days without creditable drug coverage. Not 90 days, not "a couple of months." 63.

One more warning from Medicare.gov, and it's a real one for people still on an employer plan: "If you have employer or union coverage and get Medicare drug coverage, you may lose your employer or union health and drug coverage (for you and your dependents). If this happens, you may not be able to get your employer or union coverage back." Do not sign up for a standalone Part D plan on top of an active employer plan without calling your benefits administrator first.

When you do move to Part D, the 2026 rules are more generous than they used to be: no plan may have a deductible over $615, and your out-of-pocket spending on covered Part D drugs is capped at $2,100 for the year. We covered that cap in detail for Rifle and Glenwood Springs.

Sources: Medicare.gov — Working past 65 · Medicare.gov — Creditable prescription drug coverage · Medicare.gov — How much does Medicare drug coverage cost? · Medicare.gov — Who pays first?.

Who's actually still working out here at 65?

A lot of people — more than in most of Colorado, and far more than in the rest of the Western Slope.

According to the Census Bureau's American Community Survey 5-year estimates for 2019–2023, 40.2% of Garfield County residents aged 65 to 74 are in the labor force, against 29.4% statewide. The county's employment-to-population ratio for that age group is 38.9%, meaning nearly all of those people are actually working rather than looking for work. With 5,874 residents in the 65–74 bracket, that works out to roughly 2,360 people in Garfield County who are Medicare-age and still on the job. Another 6.5% of the county's 2,953 residents aged 75 and over are in the labor force too.

Source: US Census Bureau — ACS 2019–2023, Table S2301 (Employment Status) — labor force participation rate, population aged 65 to 74, American Community Survey 2019–2023 5-year estimates, retrieved August 2026. ACS figures are survey-based estimates with margins of error. The 2,360 figure is our own calculation from the two published values, not a separately published count.

The spread across the region is striking. In Ouray County, fewer than one in seven residents aged 65–74 is in the labor force. In Garfield County it's two in five, and in Pitkin County nearly one in two. That mirrors what the two economies look like: retirement-destination counties on one end, working counties with expensive housing and a long construction, energy, hospitality, and service payroll on the other.

The practical upshot for readers here is simply that this decision comes up far more often in Garfield County than the national Medicare literature assumes. Most Medicare guidance is written for people who retire at 65. Two in five of your neighbors in that age bracket don't.

Source: US Census Bureau — ACS 2019–2023, Table S2301 (Employment Status).

The Medigap clock you're also delaying

Here's a consequence of delaying Part B that almost nobody mentions, and it's worth understanding before you decide.

Your Medigap Open Enrollment Period — the one-time, six-month window when an insurance company cannot refuse to sell you a Medicare Supplement policy, cannot charge you more for pre-existing conditions, and cannot use medical underwriting — starts the first month you have Part B and are 65 or older. It does not start at 65 if you don't have Part B yet.

That's genuinely good news for someone delaying Part B while working: your Medigap window doesn't expire while you wait. It hasn't opened yet. When you finally enroll in Part B at 68 or 71, that's when your six months begin.

The flip side is that once it does open, it's the only shot federal law guarantees you. Medicare.gov: "After this period, you may not be able to buy a Medigap policy, or it may cost more." Outside the window, insurers can deny you for health reasons except in specific guaranteed-issue situations. So the month your Part B starts is not a month to be casual about — it's a decision deadline that arrives whether you're paying attention or not. We walk through how that window and the guaranteed-issue exceptions work in our Medigap open enrollment guide.

One related item for higher earners: Part B premiums are income-adjusted, and Social Security uses your tax return from two years earlier. If you're still working, that lookback may put you in an IRMAA bracket built on your peak earning years rather than your retirement income. The 2026 surcharges begin above $109,000 in individual income and $218,000 filing jointly, and there's a form to appeal after a life-changing event like retirement — we cover it in our IRMAA guide for the Roaring Fork Valley.

Sources: Medicare.gov — Medigap: get ready to buy · CMS — 2026 Medicare Parts A & B Premiums and Deductibles.

Your checklist before you retire

An order of operations. Most of it is phone calls and paperwork, and most of it is free.

1. Get the headcount in writing. Ask your benefits administrator: how many employees does the company have for Medicare Secondary Payer purposes, and does the plan pay primary or secondary for employees 65 and older? Save the reply.
2. Decide about Part A at 65. Premium-free and no HSA? Usually take it. HSA in the picture? Read the next line first.
3. If you have an HSA, stop contributions six months out. Tell payroll as well as yourself — employer contributions count against the same limit.
4. Find your creditable-coverage notice. Your drug plan sends one every year. Put it somewhere you'll find it in three years.
5. Pick your retirement month, then work backward one month. Sign up for Part B the month before coverage ends so Medicare starts without a gap.
6. Request the employer form early. The SEP application needs a form your employer completes proving you had job-based coverage while working. Ask weeks ahead, not days.
7. Don't treat COBRA as a bridge. Your 8 months started when the job did.
8. Diarize the Medigap window. Six months from the first month you have Part B at 65 or older. That's your one guaranteed-issue shot.
9. Sort out drug coverage in the same motion, so you never cross 63 days without creditable coverage.
10. Get free, unbiased help if you want a second opinion. Colorado's State Health Insurance Assistance Program (SHIP), run through the Division of Insurance, offers one-on-one counseling at no cost and sells nothing.

Sources: Medicare.gov — Working past 65 · Medicare.gov — When can I sign up for Medicare? · Medicare.gov — Medigap: get ready to buy · Colorado Division of Insurance — Senior health care & Medicare (SHIP).

We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Assistance Program (SHIP) to get information on all of your options. Bemis Insurance is a licensed independent insurance agency. Not connected with or endorsed by the United States government or the federal Medicare program. This article is education, not advice — it is not tax advice, and HSA questions in particular should go to a qualified tax professional. Confirm your employer's size, your plan's primary/secondary status, your eligibility, and your costs with your benefits administrator, Social Security, and Medicare.gov. Figures above are published federal rules and amounts for plan year 2026, US Census Bureau County Business Patterns 2022 establishment counts, and American Community Survey 2019–2023 5-year estimates; each is linked to its source. Census figures are estimates subject to sampling and disclosure limitations and describe establishments and populations, not any individual employer.

Sources

• Medicare.gov — Working past 65
• Medicare.gov — Who pays first?
• Medicare.gov — COBRA coverage
• Medicare.gov — When can I sign up for Medicare?
• Medicare.gov — When does Medicare coverage start?
• Medicare.gov — Special Enrollment Periods
• Medicare.gov — Avoid late enrollment penalties
• Medicare.gov — How much does Medicare drug coverage cost?
• Medicare.gov — Creditable prescription drug coverage
• Medicare.gov — Medigap: get ready to buy
• Medicare.gov — Medicare costs
• CMS — 2026 Medicare Parts A & B Premiums and Deductibles
• CMS — Small Employer Exception (Medicare Secondary Payer)
• CMS — 5 things you need to know about signing up for Medicare
• IRS — Publication 969, Health Savings Accounts and Other Tax-Favored Health Plans
• SSA — Sign up for Part B only
• US Census Bureau — County Business Patterns
• US Census Bureau — ACS 2019–2023, Table S2301 (Employment Status)
• Colorado Division of Insurance — Senior health care & Medicare (SHIP)
• SHIP National Technical Assistance Center — find your local SHIP