A non-government entityMyMedicarePlans
Speak to a Licensed Insurance Agent
855-729-3240 TTY: 711
Monday – Friday: 7am – 9pm CST
HomeMedicare 2026North CarolinaWinston SalemMedicare in Winston Salem: Two Structures, One Choice

Medicare 2026

Medicare in Winston Salem: Two Structures, One Choice

WINSTON-SALEM, N.C. — For people turning 65 in the Triad this fall, the choice between Original Medicare paired with a Medigap policy and a Medicare Advantage plan often comes down to something less glamorous than benefits: the calendar. Miss the right window, and the door to one of those two paths can quietly narrow — sometimes for good.

See Medicare options in your area

Compare Medicare options near you

Answer 3 quick questions to see Medicare listings from licensed insurance partners.

✓ Free  ·  ✓ Takes 20 seconds  ·  ✓ No name, phone, or email needed

What’s your ZIP code?

Plan availability is set by your county, so we start here.

How old are you?

This helps match you with options you’re eligible for.

Do you have Medicare Parts A & B?

This affects which Medicare options you can choose.

Medicare options in your area

These listings are provided by licensed insurance partners.

2027 PLAN ALERT

Medicare Advantage plans in your area are changing or leaving for 2027.

One call tells you whether your plan is on the list — before enrollment opens.

Available now — current wait: 0 min

A real person answers. No phone menu, ever.

Call 855-729-3240
Annual Enrollment: Oct 15 – Dec 7

Advertising disclosure: MyMedicarePlans.org may be compensated when you contact a partner or licensed agent. Listings are not ranked or endorsed by us, and we do not recommend specific plans. You can also contact Medicare.gov, 1-800-MEDICARE, or your local SHIP.

Speak to a Licensed Insurance Agent

Click to call 855-729-3240

TTY: 711
Monday - Friday 7am - 9pm CST

BEFORE YOU ENROLL

Found a plan you like online?

One free call confirms it's actually right for you — online directories are wrong more often than you'd think.

  • Your doctors — confirmed in-network for 2027
  • Your prescriptions — checked against the plan's 2027 drug tiers
Verify it in one call

855-729-3240 · free · about 5 minutes

Video: Celeste 2305 Video by Celeste 2305 on Pexels

Key takeaways

  • Your one-time Medigap Open Enrollment Period lasts six months, starts when you're 65 and enrolled in Part B, and is the only federally guaranteed window to buy any Medigap policy without medical underwriting.
  • Medicare's Annual Enrollment Period runs Oct. 15 through Dec. 7 each year, and it's when most people can join, switch, or drop a Medicare Advantage or Part D plan.
  • The Medicare Advantage Open Enrollment Period, Jan. 1 through March 31, lets people already in an Advantage plan make one change — it does not let you jump from Original Medicare into Advantage for the first time.
  • Part D has a $2,100 out-of-pocket cap and a maximum $615 deductible in 2026, and a $2,400 cap and $700 maximum deductible in 2027; the old coverage gap is gone.

The two structures are built differently, and so are the deadlines that govern them. Knowing which clock is ticking is often more important than knowing which path sounds better on paper.

Two structures, two very different clocks

Original Medicare is the federal program itself — Part A (hospital) and Part B (medical). A Medigap policy is sold by a private insurer and sits on top of Original Medicare to help pay the shares Medicare leaves behind. A stand-alone Part D plan handles prescriptions.

Medicare Advantage (Part C) is the alternative. A private plan, approved by Medicare, delivers your Part A and Part B benefits in one package and usually folds in Part D. It typically uses a network and requires you to follow plan rules for referrals and prior authorization.

Because Medigap is medically underwritten in most states after your initial window, and Medicare Advantage is not, the deadlines behind each path are not interchangeable. That's where Winston-Salem residents most often get tripped up.

The Medigap window that only opens once

Your Medigap Open Enrollment Period is a six-month stretch that starts the month you're 65 and enrolled in Part B. During those six months, insurers in North Carolina must sell you any Medigap policy they offer at their best available rate, regardless of your health history.

After that window closes, insurers can generally ask health questions and can decline you or charge more. There are limited "guaranteed issue" situations later — for example, if certain coverage ends involuntarily — but they're narrow. If you think you might ever want Medigap, the safest moment to buy it is inside that first six months.

The Advantage and Part D windows that repeat

Medicare Advantage and Part D have their own recurring calendar, published by CMS on Medicare.gov:

What happens if you miss a window

Missing Part B enrollment when you're first eligible can create a lifetime late-enrollment penalty tacked onto your Part B premium. Missing Part D — going 63 days or more without creditable drug coverage — creates a separate Part D late penalty that also lasts as long as you have drug coverage.

Missing your six-month Medigap window is different. There's no penalty; the risk is that you may not be able to get the Medigap policy you want later, or you may pay more based on health.

And missing AEP simply means waiting another year for most plan changes, unless a Special Enrollment Period applies.

How the dates interact in real life

A common Forsyth County scenario: someone joins a Medicare Advantage plan at 65, uses it for a few years, then wants to move to Original Medicare plus Medigap. The Advantage exit is easy — AEP or MA-OEP handles it. The Medigap purchase is the hard part, because the one-time guaranteed-issue window has usually closed.

Another scenario: someone picks Original Medicare and a Medigap policy at 65, then wants to try Advantage later. That switch is generally allowed during AEP. Coming back to Medigap later, though, runs into the same underwriting question.

The point isn't that one path is better. It's that the two paths are not equally reversible, and the calendar is the reason.

2027 program updates worth knowing

Whichever path you choose, the drug side of Medicare keeps shifting. Part D has a hard annual out-of-pocket cap on covered drugs of $2,100 in 2026 and $2,400 in 2027, and a maximum deductible of $615 in 2026 and $700 in 2027. The old "donut hole" coverage gap is gone, replaced by a simpler three-phase design. The Medicare Prescription Payment Plan lets you spread your drug costs across the year in monthly installments instead of paying large amounts at the pharmacy counter.

Higher-income beneficiaries also face IRMAA surcharges on Part B and Part D premiums, which in 2026 begin above $109,000 in income for a single filer, based on tax returns from two years earlier.

Where Winston-Salem readers can get personal help

Plan availability in Forsyth County changes each year, and comparing options against your own doctors, medications, and budget is not something to guess at.

By the numbers

Medicare Part B premium, 2006–2026

The standard monthly Part B premium has climbed from $88.50 in 2006 to $202.90 in 2026. Hover any point for that year’s premium.

$0$50$100$150$200200820122016202020242026

Source: CMS. Standard premium shown; in some hold-harmless years many existing enrollees paid less. Confirm at Medicare.gov.

Compare with a licensed agent

See Medicare options serving Winston Salem & speak with a licensed agent

Provided by licensed insurance partners; MyMedicarePlans.org may be compensated. Not a ranking or endorsement of any plan.

Explore

When can you enroll? An interactive year

JFMAMJJASOND
October 15 – December 7 — anyone with Medicare can join, switch, or drop a Medicare Advantage or Part D plan. Changes take effect January 1.

Enrollment windows are federal and the same nationwide. Confirm your personal dates at Medicare.gov or 1-800-MEDICARE.

Explore

The parts of Medicare

Part A covers inpatient hospital stays, skilled nursing facility care, hospice, and some home health care. Most people pay no premium for Part A.

Good to know

Frequently asked questions

When does my six-month Medigap Open Enrollment Period start?
It starts the first month you are both 65 or older and enrolled in Medicare Part B, and it runs for six months. During that time, insurers in North Carolina cannot use your health history to deny you a Medigap policy or charge you more. Once it ends, that protection generally does not come back.
Can I switch from Medicare Advantage to Original Medicare during the Jan. 1–March 31 window?
Yes. The Medicare Advantage Open Enrollment Period lets people already in an Advantage plan switch to a different Advantage plan or return to Original Medicare and add a Part D plan. However, moving back to Original Medicare does not automatically guarantee you a Medigap policy — that depends on your situation and state rules.
What if I miss the Oct. 15–Dec. 7 Annual Enrollment Period?
For most people, you'll have to wait until the next AEP to join, drop, or change a Medicare Advantage or Part D plan. The exceptions are the MA-OEP for people already in Advantage plans and Special Enrollment Periods triggered by qualifying life events, such as moving or losing other coverage.
Is there a penalty for delaying Medigap?
There's no federal late-enrollment penalty for Medigap the way there is for Part B or Part D. The consequence is different: after your six-month window, insurers can typically use medical underwriting, which may affect whether you qualify or what you pay. ## The bottom line Both paths are legitimate ways to get Medicare coverage in Winston-Salem, and both are used by thousands of people across Forsyth County. The structural difference matters most on the day you sign up — and on the day you try to change your mind. For personalized guidance, start at Medicare.gov, call 1-800-MEDICARE, or reach out to North Carolina's SHIIP counselors before your next deadline arrives.
Sources & further reading
  • CMS — Medicare basics (medicare.gov)

For personalized answers, contact Medicare.gov, 1-800-MEDICARE, or your local SHIP.

Also for Winston Salem

Content Integrity Standards

  • No invented figures. Program-level numbers come from CMS / Medicare.gov; we never use placeholder data.
  • No plan rankings or recommendations. This is educational content. We don't rank, score, or recommend specific plans.
  • AI-assisted, human-reviewed. Articles are produced with AI-assisted tools and reviewed by the responsible desk before publishing.
  • Inline sourcing. Facts and figures are cited to primary sources — CMS, SSA, and Medicare.gov.
  • Correction transparency. We fix errors openly and note when a page was last updated.
  • Not a government site. MyMedicarePlans.org is privately owned and not affiliated with or endorsed by Medicare or any government agency.

This page was last updated: September 29, 2026.

Medicare plans in your area changing for 2027 — check yoursCall