4/26/26 – Round Robin with February Sky

“Rain, Shine and Re-Emergence,” an online round robin concert with the wonderful eclectic folk duo Ashley & Simpson, 5:00 p.m. Eastern Time, 4:00 p.m. Central, 3:00 p.m. Mountain, 2:00 p.m. […]
5/17/26 – Tunes & Tales at Two Way Street Coffee House

Tunes & Tales is a new songwriter-in-the-round series at the Two Way Street Coffee House, hosted by Ashley & Simpson—directors of the venue and a songwriting folk duo. Each session […]
7/19/26 – Ashley & Simpson at Woodstock Folk Festival

The 41st Annual Woodstock Folk Festival will be held on Sunday, July 19 from Noon to 6 pm on the historic Square in Woodstock, Illinois. It will include local and […]
4/12/26 – Heritage Matinee Series

Welcome to the second season of the Heritage Matinee Series at the Two Way Street Coffee House! We are thrilled to announce the continuation of this successful concert series at […]
4/12/26 – Open Mic at Two Way Street

We are always closing out the night at the Two Way Street Open Mic! Come join in the fun! More info at www.twowaystreet.org
3/24/26 – Live on Folk Festival 90.9 WDCB

We’re making a live appearance on Lilli Kuzma’s Folk Festival on 90.9 WDCB in support of their pledge drive! Be sure to tune in!
2/8/26 – Tunes & Tales

Tunes & Tales is a new songwriter-in-the-round series at the Two Way Street Coffee House, hosted by Ashley & Simpson—directors of the venue and a songwriting folk duo. Each session […]
1/25/26 – Friendly Music Community

Good music doesn’t just happen at night. Chicagoland’s phenomenal duo, Ashley & Simpson will be joining Miguel and I as our next musical guests, possibly along with some other surprise […]
1/20/26 – Fitzgerald’s Side Bar

FITZGERALDS SONGWRITER CIRCLE: w/ Host Jenny Bienemann and guests Ashley & Simpson and Paige Hargrove FREE SHOW! Click “Book Now” to make a reservation Grab dinner before the show at BABYGOLD […]
12/26/25 – Two Way Street Coffee House

Two Way Street Coffee House is Chicagoland’s most beloved folk and acoustic music venue, presenting weekly concerts and community events for over 50 years! The show starts at 8pm (CT) […]