At the null of Chestnut Mountain sits a small piece of heaven. 

Historically known as the Medford Farm, Chestnut Ridge Venue is surrounded by a family homestead on a 150 acre farm. As previous tobacco farmers, Chestnut Ridge is still a successful working farm full of homegrown sugar cane for old fashioned, vatted molasses and grazing livestock.



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the greggs

meet the founders

Taylor and Preston are college sweethearts (Go Wolfpack!!) and love all things that have to do with the Mountains they call home. Chestnut Ridge owners, Preston and Taylor Gregg, were married on this raw land over 8 years ago and from that day forward began to dream of sharing their love for this land with couples just like you. As if weddings don’t keep them busy enough, Taylor and Preston have three precious little blessings (3 boys under the age of 4!!) and 1 four-legged fur baby who they spend every ounce of their down time with. Originally from this land, Preston always knew that this would be his forever home and the place he’d one day raise his family. Taylor’s first experience outside of her hometown of Charlotte was eye opening to say the least; she literally couldn’t think of a more beautiful spot to marry the love of her life and begin her dream life as an entrepreneur.

taylor and preston

college sweethearts
parents to three boys
dog people
married at Chestnut Ridge

we'd love to have you

come and visit with us

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our philosophy

Chestnut Ridge believes in the lasting experience. This is where we transcend the expected by offering breath-taking views, meaningful amenities, and the freedom to dream. Chestnut Ridge is where you’ll truly meet your memories. From weddings, conferences, luncheons, and business events, we look forward to sharing our piece of home with you.

She loves all things southern, sweet tea and chocolate (although not together!!), and homemade pound cake with her coffee (yes….always together!!). She is humbled that she is able to run her dream business from her home base and thankful that she can share this blessing of home with all of her couples, their families and guests. As the Founder of Chestnut Ridge, Taylor credits her history in wedding planning since 2013 to her success in the industry. She did extensive research working for other venues in Asheville, and planning weddings all around North Carolina (from the triad to the mountains!). She has seen almost every possible set up, situation, and dealt with all the things at Chestnut Ridge. She built and designed Chestnut Ridge with her husband, and continues to style and design parties for corporate events, family gatherings, and weddings. Loving every minute of the chaos, Taylor is by day a total boss babe to a mega successful business where she’s a total girl’s girl and by night she is a full-time mommy to a wild crew of boys who keep her nothing but busy.

Meet Taylor

founder + owner

When you think of all things creative and ultra-organized…think Maloree! Maloree is a local to Western North Carolina, growing up just down the road in Waynesville. She graduated from East Tennessee State University with a Bachelors Degree in Marketing. She was the Social Events Coordinator for her Alpha Delta Pi sorority. Because of Maloree’s nurturing personality and go-getter spunk, she was given the “Most Dependable Award” by her sorority sisters because she always puts others before herself and wants the best for everyone. She is known for her dependability, attention to detail, and total girls’ girl! Wanting someone to take care of you on your wedding day? Maloree will be there through thick-and-thin to do just that! She will go above and beyond to make your big day extra special with her creative designing skills, special unique touches, and at home personable personality.

Connect with Maloree at

Meet Maloree

lead planner

Kayla considers herself blessed to begin working alongside not only the other wonderful ladies at CR, but all of our experienced and talented vendors.
Originally from Tampa, Florida, she moved here about 7 years ago and claims WNC as her hometown any day! She holds a B.S. Degree from Western Carolina University (GO CATS!), and cheered there for 4 years. She also met her sweetheart there of 1.5 years through a mutual friend, and they couldn't be any cuter together - it's okay, go ahead stalk Insta!😉
A girly girl on the surface, but a tough cookie at heart, Kayla brings a young and creative punch to our CR Planning Team, and she can Erin Condren any bride's chaos -- don't be scared to ask!
Some of her favorite things are Homegoods, dogs, and a good Lager and to her credit she claims her weakness is Chips & Guacamole -- I think we'll forgive her.
Kayla thrives on being busy, staying organized and developing relationships with her couples so that she can truly serve their wedding day needs to the fullest throughout the planning process.
Connect with Kayla at

Meet Kayla


What would we do without you Tiff? We're so honored that this chick has chosen CR as her side hustle! The longest standing CR employee, Tiffany holds the medals to so many amazing things. She seriously witty, and is always up for a good dance party. Put this girl on the dance floor -- you won't regret it!
We love the energy that Tiffany brings to any event that she works. As our Sr. Event Sales Associate, Tiffany manages venue responsibilities on your big day greeting you with a warm smile  as soon as you get to the bridal suite on the day of your event. She can be doing anything from cleaning up a spill on the dance floor, welcoming guests, and even lighting all those beautiful candles!

She loves all things CR, and we love all things Tiff!

Meet Tiffany

Sr. Event Sales Associate

At CR, we love what we do and who we get to do it with. From the time we open our doors until we lay our heads down at night, each of us have a passion for doing weddings. Whether we're the person from whom you receive your first email, or the staff who takes you on your tour, even fast-forward to the day of your wedding and we're mixing you your drink-of-choice...we love taking care of Y O U in all that we do.
We hope you view us as not just your wedding day crew, but as a true family. We care about you, and we take great pride in our expertise. Serving you is our priority and we will each work tirelessly to go above and beyond the call of your duties on your wedding day and all the days leading up to it.
With that said, and on behalf of all of us here at CR, 

Meet the CR Crew

Welcome to the Family!

Event Staff & Bartending Team

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