Jessica Singerman

What I Love:

Painting, drawing, riding bikes with friends, running, hiking, yoga, basically anything outside in nature… adventuring!

Riding with TT Since:


Trek Travel Role:

Guide | Trip Design Coordinator

My Favorite Ride:

In Tuscany, the loop from Pienza to Bagno Vignoni and Montalcino is awesome. On this ride, you can soak your feet in the thermal waters at Bagno Vignoni, see the monks chanting at the Abbazzia di Sant'Antimo, have a slice (or 2) of great pizza in Montalcino, and wash it down with a Brunello while you're at it. It's a hilly, challenging ride, with fast sweeping descents, and gorgeous views of the countryside dotted with villages. What more could you want?

My Rides:

Trek Domane, Trek Boone, Trek Superfly, Trek FX, Badger Custom Road, Salsa Chili con Crosso, Gary Fisher Excalibur converted to SS (yes, it’s an embarrassingly long list of bikes!)




MFA - Painting, University of Delaware BA - Studio Art, College of William and Mary RYT-500 - Yoga Teacher, YogaLife Institute

Current Home:

Winston-Salem, NC


French, Italian and Spanish

In My Previous Life:

Artist, Art Instructor and Creativity Coach, Yoga Teacher, Graphic Designer, Trip Design Coordinator…