Wayne County Kentucky Sleeping in the Woods Songwriter Festival
At Hidden Ridge Camping, the trees, the lake air and the quiet between sets do the talking. The Sleeping in the Woods Songwriter Festival brings more than twenty singer-songwriters to a wooded campground on the shore of Lake Cumberland near Monticello, where the audience camps within earshot of the stage. It is a small gathering by design, and its four documented editions from May 2023 through May 2026 show a festival that found its shape early. The organiser’s own layers print the sheet’s exact name; the shorter forms beside it — “Sleeping In The Woods Festival” in a country-music news layer and “Sleeping in the Woods” in a music-publication review layer — are recorded here unmerged.
About the Festival
The Sleeping in the Woods Songwriter Festival is a weekend of songwriter rounds, traditional sets, workshops and camping at Hidden Ridge Camping, also styled Hidden Ridge Campground, near Monticello in Wayne County. Monticello is the county seat of Wayne County, and the campground sits in forest along Lake Cumberland. Songwriter Nicholas Jamerson curates and hosts the festival, and the organising body trades under the festival’s own name, “Sleeping in the Woods Festival”. The material read gives no incorporated organiser name.
Songwriter rounds put writers shoulder to shoulder on stage, trading verses and the stories behind them, while traditional sets let one performer hold the room on its own. An interactive songwriter workshop runs on the Saturday morning of the most recent edition, and the 2025 review layer adds a yoga session and family activities, including a kids’ set and a drum circle. Camping and glamping on site keep the audience in the woods overnight. The event is ticketed: the organiser’s own newsletter layer for 2026 announces daily tickets on sale, but no ticket price is printed in the layers read, and none is stated here. The Cornbread Festival, the Wayne County Fair and the Lake Cumberland Fall Fest are different Monticello events.
Quick Facts
| Detail | Information |
| Festival name | Sleeping in the Woods Songwriter Festival |
| Host town | Monticello, Wayne County |
| County seat | Monticello is the county seat of Wayne County |
| Venue | Hidden Ridge Camping, also styled Hidden Ridge Campground, near Monticello on Lake Cumberland |
| Curator and host | Songwriter Nicholas Jamerson |
| First edition | May 2023, billed as the inaugural edition |
| Most recent edition documented | May 15–16, 2026, billed the 4th annual |
| Format | Songwriter rounds, traditional sets, workshop, camping and glamping |
| Admission | Ticketed; daily tickets on sale for 2026, no price printed in the layers read |
| Name origin | Named after one of Jamerson’s most popular songs, “Sleeping in the Woods” |
History
The festival began in May 2023, when a music magazine preview layer published on May 16, 2023 announced the inaugural edition in Monticello, hosted by Nicholas Jamerson, with Jim Lauderdale, Bella White, Lucas Wayne and Rachel Baiman scheduled, and Jamerson’s album release the same weekend on May 19. The preview layer states the festival was named after one of Jamerson’s most popular songs, “Sleeping in the Woods”, and calls it “Kentucky’s newest music festival” at its 2023 inaugural. The song gave the festival its title, and the title gave it its setting.
The second annual edition followed on May 17–19, 2024, billed the second annual by a music-publication dispatch layer. A country-music news layer gives the same dates and the Hidden Ridge venue, with more than twenty songwriters including Cristina Vane, Darrell Scott and Hunter Flynn, and a songwriter workshop hosted by Rachel Baiman.
For a useful comparison, see the Wayne County Kentucky Lake Cumberland Fall Fest Festival for another county festival.
The third iteration arrived in May 2025 and tested the festival’s nerve. A review layer documents that Friday’s slate was wiped out by severe storms and tornadoes nearby, and the festival ran Saturday and Sunday, May 17–18, 2025, with Aaron Raitiere, Ben Sollee, Emily Jamerson and others, plus a yoga session, a workshop and a kids’ set and drum circle. The lost Friday did not end the gathering: the Saturday and Sunday that followed carried the music, the workshop and the family programme as planned.
The fourth edition, May 15–16, 2026, was billed the “4th annual” by the organiser’s own newsletter layer. A state magazine events layer lists Friday gates at 11 a.m. with music from 3 p.m. to 11 p.m., and Saturday from 10 a.m. to 11 p.m., while an event-listing layer describes over twenty songwriters and an interactive songwriter workshop on Saturday morning. The billings — second annual in 2024, third iteration in 2025, 4th annual in 2026 — are recorded as printed and are consistent with the documented 2023 launch.
What to Expect
On the Friday of the 2026 edition, gates open late in the morning, with music from the afternoon into the late evening, and Saturday runs from morning to night. Because the audience camps on site, the hours between sets belong to the campground itself — a walk through the trees, a meal at a campsite, a conversation with a neighbour.
The music comes in two forms that reward different kinds of listening. Songwriter rounds gather several writers on one stage, each taking a turn with a song and the story that sits behind it, so the audience hears a new voice every few minutes. Traditional sets give one performer the stage for a longer stretch, and the 2024 roster shows the range, from Cristina Vane and Darrell Scott to Nicholas Jamerson and The Morning Jays. The 2023 inaugural roster set the same pattern, with Jim Lauderdale, Bella White, Lucas Wayne and Rachel Baiman scheduled.
The interactive songwriter workshop on Saturday morning is the festival’s most practical offering. Rachel Baiman hosted it in 2024, and the 2026 edition carries one on Saturday morning, so the session recurs rather than appearing once. It is aimed at writers and at listeners who want to understand how a song moves from an idea to a finished verse. Families are part of the picture too: the 2025 review layer records a yoga session and a kids’ set and drum circle, and the 2026 event-listing layer describes family activities.
Planning Your Visit
The first decision is the ticket. The organiser’s own newsletter layer for 2026 states daily tickets are on sale, and no ticket price is printed in the layers read, so check the organiser’s own website for ticketing before travelling.
The second decision is the stay. Camping and glamping on site are part of the festival’s format, so the natural choice is to sleep in the woods the festival is named for: a tent or a glamping pitch keeps the walk to the stage short. Monticello, the county seat, sits nearby for supplies and fuel, and the town stands on the shore of Lake Cumberland.
Timing matters most on the Friday. The 2026 edition opens its gates at 11 a.m. on Friday, with music from 3 p.m. to 11 p.m., and Saturday runs from 10 a.m. to 11 p.m., so an early Friday arrival leaves time to set up camp before the first set. The 2025 edition is a reminder to watch the weather: Friday’s slate was wiped out by severe storms nearby, and the festival ran Saturday and Sunday instead. Packing follows the setting: layers for cool night air, sturdy shoes for uneven ground, rain gear and a torch, plus a chair or blanket, water and snacks, and ear protection for younger children. The Saturday morning workshop rewards a notebook and a pen for anyone who writes, or who wants to start.
A Sample Itinerary
A two-day visit built on the 2026 schedule begins on Friday morning, when gates open at 11 a.m. and the campground fills with arrivals setting up camp. The afternoon is for settling in — a walk through the trees, a meal at the campsite — before the music starts at 3 p.m. The Friday evening then belongs to the sets, running through to 11 p.m., with rounds and traditional sets alternating as the light fades.
Saturday opens with the interactive songwriter workshop in the morning, where writers and listeners sit together and talk about how songs are made — the best preparation for the afternoon, since the rounds that follow make more sense once the craft behind them has been named. From late morning the music runs through to 11 p.m., with more than twenty songwriters across the weekend and family activities filling the gaps between sets. A shorter visit can rest on Saturday alone, but the Friday arrival earns its keep: the campground settles on Friday, and Saturday begins with the site already feeling like a temporary village. Either way, the lake is worth an hour on the way out.
How It Compares
Among Monticello’s events, the songwriter festival occupies a distinct corner. The Lake Cumberland Fall Fest is a two-day country-music gathering at Monticello-Wayne County Memorial Park with food trucks, arts and crafts and a free concert billing; the songwriter festival is smaller, wooded, camped and ticketed, with its focus on the craft of writing rather than the scale of the crowd. The Cornbread Festival at Mill Springs Mill and the Wayne County Fair are different Monticello events again.
Set against the wider run of Kentucky songwriter gatherings, the festival’s defining features are its venue and its size. A campground on the shore of Lake Cumberland is not a downtown stage or a fairground grandstand, and a roster of more than twenty songwriters fills two days without becoming a sprawling multi-stage event. The workshop thread — Rachel Baiman hosting in 2024, an interactive session on Saturday morning in 2026 — gives it a working character. The 2025 edition adds a further point: a festival that loses its Friday to severe storms nearby and still delivers a full Saturday and Sunday has a resilient format.
Checklist
- Check the organiser’s own website for ticketing before travelling; no price is printed in the layers read
- Decide between camping and glamping on site, and book the pitch early
- Arrive on Friday morning, when gates open at 11 a.m., to set up camp before music starts at 3 p.m.
- Bring layers for cool night air, sturdy shoes for uneven wooded ground, rain gear and a torch
- Carry a chair or blanket, plus water and snacks
- Pack a notebook and pen for the Saturday morning songwriter workshop
- Bring ear protection for younger children at the evening sets
- Watch the weather forecast for the weekend, since the 2025 Friday was lost to severe storms nearby
- Plan a stop in Monticello for supplies, and allow an hour by Lake Cumberland
- Keep the Cornbread Festival, the Wayne County Fair and the Lake Cumberland Fall Fest separate; each is a different Monticello event
Beyond the Festival
Monticello rewards a longer stay. As the county seat of Wayne County, it stands on the shore of Lake Cumberland, and the lake is the natural extension of a festival weekend: a morning on the shore before the gates open, or an evening walk after the last set, is the quiet counterpart to a day of listening.
The wider county holds the other events this article fences out. The Lake Cumberland Fall Fest fills Monticello-Wayne County Memorial Park with country music in the autumn, the Cornbread Festival gathers at Mill Springs Mill, and the Wayne County Fair carries the county’s agricultural calendar. None of them shares the songwriter festival’s wooded campground format: Wayne County’s calendar has room for a park concert, a mill festival, a county fair and a weekend in the woods. For visitors who write, the workshop thread is the lasting thread: the morning names the tools, and the afternoon shows them in use.
Why It Matters
The festival matters because it gives songwriters a clearing where the song itself is the event. A music magazine preview layer called it “Kentucky’s newest music festival” at its 2023 inaugural, and the four editions that followed show why that label stuck: the festival did not grow by adding stages or spectacle, but by returning to the same wooded campground with the same shape, a roster of more than twenty writers, a workshop, and an audience that camps within earshot. The name, taken from one of Nicholas Jamerson’s most popular songs, is the festival’s programme in miniature.
It matters too because the record is unusually complete for a young festival. Four consecutive editions, 2023 through 2026, are documented with dates, lineups, venue and format, and the 2025 edition’s lost Friday is recorded as honestly as the editions that ran in full. A festival that can show its bad weather alongside its good weekends is a festival whose record can be trusted.
Frequently Asked Questions
What makes this festival different from other music weekends in Monticello?
The setting and the focus set it apart. The festival takes place at Hidden Ridge Camping, a wooded campground on the shore of Lake Cumberland, where the audience camps on site, and its programme centres on songwriter rounds, traditional sets and an interactive workshop. The Lake Cumberland Fall Fest, the Cornbread Festival and the Wayne County Fair are different Monticello events.
Who curates and hosts the festival?
Songwriter Nicholas Jamerson curates and hosts the festival, and the organising body trades under the festival’s own name, “Sleeping in the Woods Festival”. The material read gives no incorporated organiser name.
Is the festival ticketed, and what do tickets cost?
The event is ticketed. The organiser’s own newsletter layer for 2026 states daily tickets are on sale, but no ticket price is printed in the layers read, so no price is stated here. The organiser’s own website carries the ticketing routes.
What happened to the 2025 edition?
Friday’s slate was wiped out by severe storms and tornadoes nearby, and the festival ran Saturday and Sunday, May 17–18, 2025, with Aaron Raitiere, Ben Sollee, Emily Jamerson and others, plus a yoga session, a workshop and a kids’ set and drum circle, as a review layer documents.
What to Expect From the Next Wayne County Kentucky Sleeping in the Woods Songwriter Festival
How often is Wayne County Kentucky Sleeping in the Woods Songwriter Festival held?
The documented record shows an edition in each of four consecutive years, May 2023, May 2024, May 2025 and May 2026, with the 2024 edition billed the second annual and the 2026 edition billed the 4th annual. That pattern points to an annual May gathering.
When is the next Wayne County Kentucky Sleeping in the Woods Songwriter Festival?
The layers read carry no announcement of a following date. The most recent edition documented is May 15–16, 2026, and the pattern so far places the gathering in May, but no date for a following edition has been published in the material read.
Will the dates change?
The dates have moved within May from year to year: the inaugural edition fell in May 2023, the second annual ran May 17–19, 2024, the third iteration ran May 17–18, 2025, and the 2026 edition ran May 15–16. A future edition may again fall on a different May weekend, so check the organiser’s own newsletter and website before planning a trip.
The Sleeping in the Woods Songwriter Festival is a small, wooded, listening-first weekend that has held its shape across four May editions: more than twenty songwriters, a Saturday workshop, a campground that stays awake with the music, and a lake at the edge of the trees.
