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Boonesboro Trail Senior Living

2101 Old Boonesboro Road

4.7(21 ratings)

Part of Trilogy Health Services · all operators · 161 communities · 4.2★ average

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Boonesboro Trail Senior Living, photo 11 / 5

Quick Facts

Boonesboro Trail Senior Living is a senior living community in Winchester, Kentucky offering Assisted Living and Memory Care. Families rate it 4.7 out of 5 across 21 reviews.

About Boonesboro Trail Senior Living

Boonesboro Trail Senior Living in Winchester, Kentucky is an assisted living and memory care community operated by Trilogy Health Services. The community offers multiple levels of care to support seniors at different stages of independence, from independent living to assisted living and memory care services.

Assisted living services support residents who seek additional help with daily tasks, allowing them to focus on enjoying their time rather than managing appointments, medications, and chores. For residents navigating memory loss, the community employs the Best Friends Approach, which pairs residents with companions who understand their life stories. Memory care programming includes Daily Rhythms activities that provide consistent engagement throughout the day, along with fulfilling activities designed to stimulate the mind and encourage socialization.

The community features rich lifestyle programming including fitness classes, arts experiences, enrichment clubs, games, live music, and themed events. Residents are invited to participate in scheduled outings, family visits, and community events that emphasize social connection. Campus amenities include large gathering spaces, cozy nooks, libraries, community rooms, outdoor walking paths, activity areas, fitness spaces, beauty and barber services, and landscaped courtyards.

Chef-prepared meals are included as part of the everyday lifestyle experience, with menus crafted to be nutritious and accommodating of various dietary needs including heart-healthy, diabetic-friendly, and texture-modified options. Most apartments are largely unfurnished, allowing residents to bring their own furniture and belongings to personalize their spaces. Laundry and housekeeping services are included as part of most care levels.

The community is located near Clark Regional Medical Center and nearby churches including Methodist, Baptist, and Catholic congregations. Safety is supported through clinical-grade alert systems and monitoring technology available in most care levels to ensure residents can quickly receive assistance when needed.

Most Trilogy communities including this one are pet-friendly, allowing residents to bring well-behaved pets that meet community guidelines, though policies vary by location and skilled nursing areas may have exceptions. Respite care is available for short-term stays ranging from a few days to several weeks, as well as adult day services during daytime hours.

Types of Care at Boonesboro Trail Senior Living

Assisted LivingMemory Care

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Reviews of Boonesboro Trail Senior Living

4.7overall · 21 ratings combined

4.7★ on Google (21)

julia haven

Sep 2026

via Google ↗ · Report

The property is quite nice and taken care of. Great views. But this place sucks hot dogs. Whoever runs this facility treats their employees like crap and because of that alone, the employees don’t give enough attention to the sweet residents. Yes, it’s a nice place to look but there is a circus going on inside so no I wouldn’t recommend “Barnum & Baileys” senior living center to anyone.

Sandy Baker

Jul 2026

via Google ↗ · Report

My Mom has been a resident at Boonesboro Trail for 15 months and she made it home within the first three days transitioning beautifully. I observe the residence go out of their way to welcome new friends inviting them to social activities . The care givers seem to think of the residence as family . I feel so at home visiting and truly feel what a blessing to have this nice a facility in our home town of Winchester, Ky. The apartments are roomy with beautiful views of the landscaped garden. One particular thing I observed two weeks ago was the facility bought overstuffed fluffy cushions for the outdoor porch chairs much to the delight of the residence! I have always thought of the nursing staff as attentive and caring . The social activities planned amaze me including out of town travels on their nice bus. The frequent family gatherings at the table sharing a meal with other families is something I look forward to ! The eye appealing home cooked meals are delicious. The music played in the facility adds to the welcoming atmosphere . I often find myself singing along 😉. Say yes and let Boonesboro Trail Senior Living SPOIL your loved one. I have never felt alone in this journey and appreciate the support of the staff at Boonesboro Trail Senior Living . Sandy Baker

Animated_ K9_

Jul 2026

via Google ↗ · Report

We got my Dad settled into his apartment and we love it! The staff is really welcoming and helpful and we all feel really good about this decision, with all the amenities and nursing staff and delicious looking food. Hannah in particular was the best at walking us through everything from the start.

donna kosch

Apr 2026

via Google ↗ · Report

Beautiful facility, the inside is beautiful and the outside is gorgeous.

Linda Yostpile

Apr 2026

via Google ↗ · Report

Beautiful Place.. Clean Friendly and caring Staff!! Food is also Fantastic Beautiful home cooked meals

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Frequently Asked Questions

What types of care does Boonesboro Trail Senior Living offer?

Boonesboro Trail Senior Living offers Assisted Living and Memory Care.

Where is Boonesboro Trail Senior Living located?

Boonesboro Trail Senior Living is located at 2101 Old Boonesboro Road in Winchester, Kentucky.

What do families say about Boonesboro Trail Senior Living?

Boonesboro Trail Senior Living carries a 4.7 out of 5 rating from 21 Google reviews. Reviews on MyLivingChoice come from families who confirmed a connection to the community and appear with the reviewer's first name and last initial.

How can families visit Boonesboro Trail Senior Living?

Submit the Request Information form on this page, or contact Boonesboro Trail Senior Living directly, to arrange a tour. Sharing your timeline and care needs up front helps the community prepare for your visit.

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