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(859) 236-9644
About Boonesboro Trail Senior Living
Seniors can rely on Boonesboro Trail for quality of life and care. We have a friendly environment that provides a sense of health and well-being. Our residents enjoy all the local activities and entertainment that Winchester has to offer. Our community is positioned perfectly for residents to take advantage of local events.
Our community is dedicated to providing our residents compassion and kindness. We are on a mission to enrich the lives who live and work with us. We respond to each of their unique needs and the desire to maintain their dignity and respect. Each resident comes with their own set of needs and we are mindful of that. For some seniors, that need is as simple as friends and companionship, a full and active social life. Assistance with daily activities and tasks might be what others need. Some of our residents need more intensive and specialized care like therapy and rehabilitation services.
Boonesboro Trail Senior Living and Care Available
Assisted Living
Boonesboro Trail Assisted Living offers independence with support, tailored for seniors seeking a safe, comfortable lifestyle in Winchester. Services include help with everyday activities, access to common areas, and availability of professionally trained staff. With Boonesboro Trail Assisted Living, you and your family can enjoy peace of mind knowing care is always available.
Memory Care
For compassionate Alzheimer's and dementia care, Boonesboro Trail Memory Care in Winchester delivers specialized support tailored to each resident's needs. With unique and personalized wellness programs, a secured building, and mentally-engaging activities help residents thrive. You'll find comfort as Boonesboro Trail Memory Care enriches your relative's life, managing their dementia and reassuring you of their well-being.
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Boonesboro Trail Amenities & Services
We offer seniors the latest amenities in comfort that they would enjoy in the comfort of their own homes. Comprehensive Amenities are available for all residents. The staff here are fully trained, friendly and accessible. They will help your residents enjoy their stay with us.
We know that seniors need varying degrees of help as they get older, but still want to feel independent. Our facility has Ample Services and other assistance. We try to make sure that each resident is able to maintain a full life while staying with us.
Residents enjoy of a full schedule of social, educational and entertaining activities. Our structured program helps all residents maintain a high quality of life. Many of our activities encourage members to socialize and develop friendships with other residents. We make sure the activities are fun and entertaining.
If you are ready to see all that senior living has to offer, come by for a tour of our beautiful facility or call (800) 755-1458.
Boonesboro Trail Senior Living Location
Boonesboro Trail Senior Living
2101 Old Boonesboro Rd, Winchester, KY 40391
Pricing & Availability
(800) 755-1458Available Living Options
- Assisted Living
- Memory Care
Contact Us to Get Pricing & Schedule Tours
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Prefer to speak to a live person? Talk to a local senior living advisor today
(800) 755-1458
Boonesboro Trail Senior Living Frequently Asked Questions
What does Boonesboro Trail Senior Living cost?
The cost of care at Boonesboro Trail is determined by the care type, level of supervision, staffing, and support required for assisted living or memory care. Pricing may also be influenced by optional services like transportation, meals, and personalized care. Call (800) 755-1458 for customized quotes and tailored pricing.
Does Boonesboro Trail Senior Living take Medicare or Medicaid?
Assisted living is not funded by Medicare, as it focuses on non-medical needs. Medicare does not include memory care in its benefits, although certain medical services may qualify. Medicaid may help with the cost of assisted living or memory care for those who qualify based on income and need. Contact a senior advisor at (800) 755-1458 to get personalized assistance.
What care and living options does Boonesboro Trail Senior Living provide?
Boonesboro Trail offers assisted living and memory care programs tailored to each resident’s needs. Assisted living fosters independence, and memory care provides compassionate support for cognitive challenges.
Does Boonesboro Trail Senior Living have immediate openings?
Available units at Boonesboro Trail may vary often. Call (800) 755-1458 to speak with a senior living professional for current openings. A waiting list exists for times when units are fully occupied.
Are tours available at Boonesboro Trail Senior Living?
Yes, Boonesboro Trail offers tours for interested individuals. Contact the team by phone or through the contact form to arrange a convenient time to visit the community.
How do people rate their experience at Boonesboro Trail Senior Living?
Boonesboro Trail holds a strong 5.0 rating, emphasizing very positive feedback. Customers appreciated the assisted living and memory care services, praising the care, facility, and thoughtfully designed amenities.
Reviews Boonesboro Trail Senior Living
July 2026
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.
July 2026
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
April 2026
Beautiful facility, the inside is beautiful and the outside is gorgeous.
April 2026
Beautiful Place.. Clean Friendly and caring Staff!! Food is also Fantastic Beautiful home cooked meals
January 2026
Some of the staff are genuinely good people, but it often feels like most are just there for the paycheck. I find it very difficult to get responses from office staff through email (except for the head of nursing - she has been great via email). I prefer using email because at least sometimes, I’ll get a reply — whereas when I leave a voicemail, I almost never get a return call.
January 2026
So impressed with Boonesboro Trail. The staff is wonderful; friendly, professional, and seems to deeply care about the wellbeing of their residents. If you or a loved one is looking for a place to not just receive care but thrive as you age, I highly recommend.
June 2025
My mom has been a resident at Boonesboro Trail Senior Living Center for 2 years; I absolutely cannot imagine her living anywhere else. The entire staff, from top to bottom, are amazing! To a person, they treat each resident as if they were their own parents/grandparents. Boonesboro Trail has many internal activities each week and have special events for things like Mother's Day, Veterans Day, Easter, etc. They also, periodically, take the residents (they have a van/bus) to lunch at restaurants, drives in the country, etc. One thing some of the residents really enjoy is the gardening club in which they plant and take care of various flowers & vegetables in the courtyard ... they won the Trilogy Network prize for the best flower garden last year 🙂 I'm in Boonesboro Trail very frequently and have befriended many of the residents. I talk with as many of them as I can each time I'm there; I can honestly say that they're all happy and comfortable there. My mom is thriving at Boonesboro Trail Senior Living Center and very much enjoys living there! I'm REALLY glad we got my mom into the perfect place for her on the first go!
June 2025
I absolutely love this location. I’ve had the opportunity to spend time with residents at three Trilogy-owned properties in Lexington, and this one truly stands out. I confidently refer all of my clients here because of the outstanding care consistently provided. The staff genuinely cares about each resident, and it’s clear that the residents care deeply for one another as well. The assisted living campus is beautiful—extremely comfortable, thoughtfully designed, and the variety of floor plans available is simply amazing. When it comes to Memory Care, this is hands down the best place I’ve ever had the pleasure of being a part of. The compassion, professionalism, and sense of community here are unmatched.
January 2025
Boonesboro trail is always clean and beautifully decorated. The staff are all kind, caring and welcoming. The residents are all happy and well cared for and give high recommendations. I enjoy all the post of all the fun activities they hafts for their residents °
January 2025
This place is wonderful! Clean and spacious. They have a great place that cares about their employees. They cook real, authentic food for their patients. Whitney is a cook in the kitchen and she really takes pride in cooking for her residents!
October 2024
Great location and very caring staff!
October 2024
Beautiful campus! Wonderful staff!
September 2023
Definitely have to give Boonesboro Trail senior living a 10 the best place to live, food is amazing every meal, all the staff go above and beyond to help their residents feel like family. The facility inside and out is so warming you feel the welcome right away. Thank you for loving our mom
February 2023
The transition stage is never easy for a family but Boonesboro Trail has been a blessing! My mom moved in over a year ago and has been happier than I've seen her in a long time. She raves about the food, loves the staff, and has made many friends to socialize with. 10/10 recommend!!
September 2022
This is an awesome place. All the employees are very caring and they keep me up to date with what is going on with my mom. I am able to finally rest knowing my mother is being completely cared for.
August 2022
This is an extraordinary and beautiful facility that gives my mother a feeling of home away from home. The staff and chefs are excellent here, and their compassion and patience shows through their interaction with my mom and all the other residents. I would highly recommend Boonesboro Trail Senior Living to anyone that is looking to give their loved ones the care and comfort everyday when you’re not able to be with them. I feel comfort in knowing my mom is well taken care of. Thank you to each and every staff member for all you do, and know that you’re greatly appreciated.
June 2022
One of the most beautiful campuses I have ever seen! Everyone I have talked to raves about the team and delicious food at Boonesboro Trail. Would recommend to anyone!
July 2021
Excellent facility and caring staff make a wonderful living environment for my mom. The food is delicious and the location is perfect!
July 2021
Great staff and beautiful new facility. Highly recommend it.
May 2021
It's a beautiful place and it seams like the food is going to be delicious. I would love to be able to live there after I get to where I can't live without help and medical care.
Rate and Review Boonesboro Trail Senior Living
Community Details
Boonesboro Trail Amenities and Services
Amenities
- Comprehensive Amenities
Services
- Ample Services
Do you have questions? Speak to a local senior living advisor for free.
(800) 755-1458
Boonesboro Trail Housing and Staff
Living Types Available
Staff
Not sure what senior living is right for you or your loved ones? Call us today!
(800) 755-1458
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Assisted Living Center is not affiliated with Boonesboro Trail Senior Living and does not guarantee the completeness or accuracy of pricing, photos, living or care available, services or amenities. All phone calls and form submissions are handled by our trusted partner A Place for Mom. Any information regarding Medicare and Medicaid is for general informational purposes and is not a substitute for professional advice. Please visit Medicare.gov or Medicaid.gov for more information.
Families and their loved ones are encouraged to do the following before deciding on a community.
- Schedule a tour and visit the physical location to make sure community description is accurate.
- Confirm with community manager that living and services required for you or your loved one's unique needs and budget are met.
- Check with state government websites for additional provider licensing and information.
If there is any information that is inaccurate or needs to be updated, please contact Assisted Living Center.
Assisted Living Center uses the term "assisted living" or "personal care" to inform users that a community provides assistance with some Activities of Daily Living (ADL's). It may not meet your state's legal definition required for that level of care.