Wintergrass 2019 Performers-Sideline

Sideline is a pedigreed six-piece powerhouse whose style has set the pace in Bluegrass for over two decades. Founders Steve Dilling, Skip Cherryholmes and Jason Moore can all claim their own historical significance to the genre as members of highly awarded groups, multiple Grand Ole Opry appearances and years of national and international touring.
What started as a side project for the seasoned players soon moved to the front and center as the three were joined by talents of Bailey Coe; guitar, Troy Boone; mandolin, and Daniel Greeson; fiddle, and began to record and release albums in earnest.

To listen to Sideline reminds the fan of why so many people fall in love with Bluegrass in the first place; pulse-pounding drive, songs sung from the heart, perfected timing and dynamics as well as a visceral emotion in the rendering. A band that was started as an off-season fun experiment has become a full-time dream team of players and singers.

The band, recorded or live, move dynamically from well chosen, hard-hitting neo-traditional covers of classic songs to new material curated by a band with a perfect sense of who they are and what they have to say. Combine all this with their on-stage energy and finesse as well as their powerful and affecting harmonies, and you have the embodiment of the North Carolina Bluegrass sound. Sideline has released 3 national projects and currently records for the highly awarded Mountain Home Music Company based near Asheville, NC.


Steve Dilling  on banjo plays like he was born and raised in a crib where only Earl Scruggs and Tony Rice played on the twirling mobile above him. In love with the banjo at 10, playing by 12, starting The Bass Mountain Boys, then on to the Lonesome River Band, Steve’s career has had a solid, steady trajectory of success and respect. Of course we have to talk about his 20 plus years with Russell Moore and IIIrd Tyme Out. You know that Steve Dilling’s Carolina-awesome banjo playing and hilarious emcee work is one of the main reasons you always go see them when they’re in town. IIIrd Tyme Out has certainly brought his talent to the forefront of the bluegrass community. But his work with Sideline allows Steve to show audiences that he’s the real deal in any setting.

Jason Moore on bass is a long time veteran of the Bluegrass and Americana scene. He first started working in bluegrass with the legendary James King in 1993 and was there through 1999. While there he was on the award winning “Bed By The Window” project and several other King projects. Also during this time he was asked to be on two Michael Cleveland projects along with Mountain Heart. While in the group, they went from top notch Bluegrass band to Americana band, all the while, recording six band projects and numerous other projects as a session player. Jason was asked to help on such projects as “A Tribute to the King of Bluegrass, Jimmy Martin”, Tim Staffords “Endless Line” and several others. As a result of the work he has done in different bands and projects, Jason has been on three Grammy Nominated projects and been nominated for “Bass Player of the Year” at the International Bluegrass Music Awards four times to go with winning “Recorded Event of the Year” twice and “Gospel Event of the Year”. Jason’s latest ventures include starting the Bluegrass band “Sideline” and working with other nationally touring Bluegrass bands as well as studio session work and production. To date, Jason has been on close to 100 different projects and has produced two others with more in planning. every imaginable kind of bluegrass, and his timing and groove are unequaled, you’ll mostly want to tell him how amazing he is.

Skip Cherryholmes  on guitar started playing mandolin at age 9, but later switched to guitar when his family formed the “Cherryholmes” family band. Skip played with his family for almost 13 years until they decided to disband in 2011. In their time together, the Cherryholmes family won the 2005 IBMA Entertainer of the Year award, and have been nominated for numerous awards including 5 Grammy awards. He also played with bluegrass legend Lou Reid and his group “Lou Reid and Carolina”. Skip is now playing full time with Sideline and working as an engineer and producer at “Old Stage Recording Studio” in Raleigh, NC.

Troy Boone on mandolin has always had music surronding him. At a very young age, he decided to learn how to play banjo. After a few lessons, he stopped due to a lack of interest; however, his interest in music was still strong. Upon getting a Martin guitar for Christmas, Troy began learning guitar from his father. After learning the basics, he was desperate to obtain a higher knowledge of music and guitar playing. He began taking private guitar lessons from David Yates, a professional instructor out of Johnson City, Tennessee. After learning several tunes, he really began developing a deep love for bluegrass music. Each week David would teach him a new flat-picking tune. Years later, he found a mandolin which belonged to his older brother and began learning to play. Troy started to develop a strong passion for mandolin at this point, and upon graduating high school he decided to enroll in East Tennessee State University’s Bluegrass program. There Troy studied guitar, mandolin, banjo, along with taking several bluegrass education classes. Troy has been playing with his hometown band “Dreamcatcher” for the last 2 years.

Baily Coe on guitar was born raised in Four Oaks, North Carolina Bailey began playing mandolin at 11 years old. He later would switch over to guitar at the age of 18. Bailey spent two and half years with the GrassCats before coming to Sideline. Bailey is also a graduate of The University of North Carolina at Greensboro and will continue his education in Occupational Therapy. When Bailey is not on the road or playing music he enjoys spending time with his friends and loved ones, reading and playing with his two dogs Harvey and Molly. Music has always been a cornerstone of Bailey’s life and he looks forward to continuing that with Sideline.

Daniel Greeson on fiddle is from Jamestown, North Carolina, was always around music growing up and started playing fiddle when he was 6 years old. His interest in playing was sparked when his uncle found a fiddle in the trash and gave it to him. From there, Daniel began lessons with J.B. Prince. Through fiddlers conventions throughout North Carolina and Virginia, he was introduced to the JAM (Junior Appalachian Musicians) program where he met other musicians and began making connections. He has studied fiddle under J.B. Prince, Dewey Brown and Hunter Berry. Daniel is currently in the bluegrass program at East Tennessee State University. For the past 3 years, he has been traveling with the Bluegrass Gospel group, The Churchmen. He is excited to begin his new journey with Sideline.



Wintergrass 2019 Lineup!

The Wintergrass Lineup for 2019 Feb 21-24
Ben Hunter & Joe Seamons (Sat) Orchestra

Bill & the Belles(Fri/Sat)

Billy Strings (Fri) Billy Strings

Blue Highway (Sat/Sun)


Cathy Fink & Marcy Marxer(Sat)

Della Mae(Th/Fri)

Don Vappie (Sat/Sun) Orchestra

Ellis Dyson & the Shambles (Th/Fri)

Fireside Collective (Th/Fri)


Highway Home (Sun)

The Hillbenders (Fri/Sat)

Hills to Hollers (Fri/Sun) Orchestra

Jayme Stone’s Folklife (Sat/Sun)

Joe Craven & the Sometimers (Sat)

Jonathan Byrd & the Pickup Cowboys(Fri/Sat)

La Famille Léger (Th/Fri)

Molsky’s Mountain Drifters (Sat)

Old Growth Quartet (Th/Fri)

The Rolling Blackouts (Sat)

Peter Rowan Bluegrass Band (Sat/Sun) Orchestra

Phil Leadbetter All-Stars of Bluegrass
with Claire Lynch, Steve Gulley, Alan Bibey,
& Jason Burleson (Fri/Sat)

Po’ Ramblin’ Boys (Th/Fri)

The River Feale Band(Fri/Sat)

Sideline (Th)

Sons of the Pioneers (Th/Fri)

Sugar & the Mint (Th/Fri)

Steep Canyon Rangers (Fri/Sat) Rangers-St-Pete-2018-Hi-Res-8








Vivian Leva & Riley Calcagno (Fri/Sat)


Wintergrass 2019 Tickets and Room Reservations

2019 Wintergrass Tickets

Pricing good February 27, 2018 to March 31, 2018
Ticket prices include all processing fees and handling charges.


Buy tickets online for Wintergrass 2019 using our Secure Web Ticket Site.

Due to the overwhelming demand for rooms at the Hyatt Regency, Wintergrass and the hotel have teamed up to create the first ever ticket/room package. Rooms at the Hyatt for the 2018 festival sold out less than a week after the 2017 festival causing a fair amount of anxiety for those who purchased tickets in hopes of snagging one of those rooms.

This year, there are TWO Early Bird options:
We will be selling a limited number of Ticket and Room Packages. These packages will include one festival pass and one room. Please see details below.
Our standard, deeply discounted 2019 Weekend Passes which will be available through March 31st. These passes do not come with or guarantee a room at the Hyatt.
Please ensure that you choose the option that you want at check-out!
Super Early Bird Ticket and Room Package:

This Package will guarantee a reservation at the Hyatt Regency for all (3) nights of the Festival – Thu 2/21/19, Fri 2/22/19, and Sat 2/23/19.

A few things to note prior to purchasing a Wintergrass 2019 Ticket and Room Package:
A three-night minimum stay is required, to include Thu, Fri, Sat nights
Room type must be selected at the time of purchase. Available room types are: Standard King Room, Standard Double Room, Deluxe King Room, Deluxe Double Room. (Deluxe rooms are all located on higher floors.)
Preference of Quiet or Jamming floor must also be noted.
Packages are non-refundable. Exceptions will only be made in cases of medical or family emergencies.
A one-night deposit for the selected room type will be collected at the time of purchase. The remaining portion of your hotel bill will be due at the time of check in.

The Ticket and Room Package includes one weekend pass. Additional weekend passes may be purchased without the package. For example, a couple may choose a standard king room package, which includes one ticket, and then purchase a weekend pass – no need to buy two packages to get two tickets.

Prices for the one night deposit PLUS the Super Early Bird Weekend Pass are as follows and are available through March 31, 2018 (while rooms last!):

Standard King or Double room package – $279
Deluxe King or Double room package – $309

Volunteers who wish to secure a room may purchase an Intent to Volunteer package:

Volunteer Standard King or Deluxe room package – $154
Volunteer Deluxe King or Double room package – $184

The room rate for volunteers who secure a room but do not fulfill their 12-hour obligation will revert to the standard room rate (but, we know, you wouldn’t do that!).

The Super Early Bird Ticket/Room Packages and Weekend Passes will be available beginning Tuesday, February 27, 2018 online at

Remember, if you buy the package – you have a room. The Hyatt will contact all Wintergrass 2019 Package buyers on April 10, 2018 with room confirmation numbers.

Super Early Bird Ticket Only:

A Super Early Bird Weekend Pass (without a room) costs $125. There are no further discounts at this price level. Super Early Bird Weekend Pass rate is available through March 31, 2018.

Super Early Bird Weekend Passes will be available beginning Tuesday, February 27, 2018 online at

Please Note: Wintergrass does not issue paper tickets. All orders are entered into a secure database. All tickets purchased through will be marked as ‘Processing’ until you check in at the festival. At that time, they are marked at ‘Completed’.

You should receive an emailed ticket confirmation at the time of your purchase. A little over a week before the festival begins we will start sending out final ticket confirmations. These confirmations contain a barcode, which you will use to check in at Festival Registration located on the mezzanine level of the Wintergarden lobby at the Hyatt Regency in Bellevue. Check in takes seconds.

Wintergrass Refund Policy

Wintergrass does not issue refunds. Exceptions, of course, are made for medical or family emergencies.

No refund requests of any kind will be processed, responded to or otherwise acknowledged from the third week in February through the second week in March. We simply do not have the bandwidth during this time period to work on refunds. Please respect this.