1976 - Roadside scripts, produces, and begins touring regionally and nationally Red Fox/Second Hangin’, its first full length play. Red Fox premieres in Whitesburg, KY, and off-Broadway in New York City. Written from oral history and archival research, it dramatizes the coming of the first coal and timber industrialists to the mountains. Their arrival in 1891 on the Appalachian frontier was to be the watershed moment in the 20th century history of the region.
- Red Fox/Second Hangin’ establishes the company’s authenticity and artistic reputation in its home community, and draws the attention of the national press to its work.
1980 - Roadside scripts, produces, and tours Pretty Polly, its first musical theater work. Roadside’s original musical compositions and harmony singing will become hallmarks of the ensemble’s performances. Pretty Polly is the first of the "Pine Mountain Trilogy," a trio of plays that dramatize the history of six generations of an Appalachian family, 1840 to 1969.
- With the development of the Trilogy, Roadside builds a permanent ensemble of artists and managers.
- Touring the Trilogy helps Roadside build new, working class and economically poor theater audiences nationally, and brings the company recognition in the U.S. arts field as one of the nation’s few professional ensemble theaters.
- Roadside is the only rural theater selected by the National Endowment for the Arts for its Ongoing Ensembles award.
- In 1989, Roadside performs its "Pine Mountain Trilogy" at the London International Festival of Theatre, followed by a tour to the coalmining valleys of Wales.
- The Wales tour attracts international media attention as a result of the bitter strike then occurring in the Appalachian coalfields and the privatization of the Welsh mines.
- In 1993, Roadside is invited to perform Leaving Egypt in the Czech Republic and meets President (and playwright) Vaclav Havel, who attends a performance.
- In 1994, Roadside presents Junebug/Jack and RoadBug at the South Bank Centre’s "Festival of the American South" in London.
1988 - In order to broaden and deepen interaction with working class and poor communities regionally and nationally, the company decides to risk its economically successful one and two day touring engagements by replacing them with long-term, often multi-year community residencies. The theater forms partnerships with diverse audiences and local organizations to uncover and celebrate the local life of the host community and to use this celebration as a basis to address their issues; to produce original, community-created plays; and to found new theaters.
- Based on six years of tracking by an independent research firm, Roadside’s national audience comes to look strikingly different from the typical upper-middle class professional theater audience: 73 percent earn less than $50,000 annually and 30 percent of those earn $20,000 or less annually. Forty-five percent are college graduates.
- Roadside’s new residency model builds the skills of the ensemble and increases new play production.
1990 - Roadside expands its efforts to focus attention on the rich history of grassroots theater in the United States by teaching in colleges and universities.
- A three-year (1990-1993) residency at Cornell University includes the design and teaching of a course, "Issues in Community Based Art," a national symposium on the grassroots theater movement from historical and contemporary perspectives, and a retrospective of Roadside's plays.
- Over the next ten years, Roadside hones its higher education methodology through teaching residencies at The College of William and Mary, Arizona State University, New York University's Tisch School of the Arts, Mountain Empire Community College, The University of Virginia at Wise, and The University of Akron.
1991 - Roadside begins creating intercultural plays with other culturally specific, professional theaters.
- As the result of a 10-year cultural exchange and sharing of the stage with Junebug Productions, the New Orleans based African American theater company, Roadside and Junebug co-create and tour two musical plays, Junebug/Jack and RoadBug. The plays bring together working class black and white audiences to talk about their differences and celebrate what they hold in common.
- In 1996, Roadside celebrates the 11th year of a projected 20-year cultural exchange with traditional Native American artists of Pueblo Zuni in New Mexico with the co-creation and touring of the bi-lingual play, Corn Mountain/Pine Mountain: Following the Seasons. The success of the play leads to the founding of Idiwanan An Chawe, the first Zuni language theater.
- In 1998-2002, Teatro Pregones from the Bronx joins Roadside and Junebug to create and tour nationally a musical, Promise of a Love Song, which has a cast of six plus a six-member band.
- Interracial choirs assembled from different churches in the host community are incorporated into Junebug/Jack performances.
- The company works with a women’s shelter to create Voices from the Battlefront, a play with music that addresses abuse in Appalachia. The cast of Voices includes survivors of domestic violence, shelter staff, and Roadside actors.
- A cancer prevention program partners with Roadside to teach community groups to write and perform plays from their personal stories about cancer. Roadside’s professional actors participate in several of these productions.
- Roadside creates and tours New Ground Revival, a musical play written and performed with the Mullins Family Singers, three generations of Appalachian gospel singers who represent a 150-year family tradition of harmony singing.
- New Ground performances are part of a three-year exchange with the farming and ranching community of Choteau, Montana. A Choteau community theater also creates two plays from their traditions, one of which tours to Appalachian audiences.
- These collaborations and others like them deepen Roadside’s exploration of its Appalachian musical traditions. Two compact discs, "Wings to Fly" and "Journeys Home," feature the theater’s original music and the talent of its collaborators in Zuni and Appalachia.
- The company releases the music CD "Wings To Fly" (Copper Creek Records) and the book/spoken word CD set, "Journeys Home: Revealing a Zuni/Appalachia Collaboration" (Zuni A:shiwi Press) and premieres its original musical, Music From Home.
- Roadside facilitates a year-long storytelling/playmaking residency with community members in Patapsco, Maryland. The residency results in the creation of a community theater and the premieres of five original performances: Weaving the Thread of Community, Varying the Pattern, A Winter's Feast, Inside the Memory Box, and A Completely Different World.
- Roadside's Dudley Cocke co-creates and co-directs Why the Cowboy Sings, which previews at the 18th National Cowboy Poetry Gathering in Elko, NV, and premieres at the 2002 Winter Olympics in Salt Lake City.
- Roadside, with the East Bay Center as its organizational partner, works with Mien, Laotian, African American, and Mexican American communities in the Iron Triangle area outside of San Francisco, CA to create Stranger at the Table, which is presented to full houses in each community.
- Roadside, Junebug Productions, and Pregones Theater present Promise of a Love Song and facilitate storytelling workshops and music jams as a part of the cross-cultural Tamejavi Festival in Fresno, California.
- Roadside teaches its grassroots theater course at the University of Akron in Ohio, which results in a student production, Circle Stories.
- Roadside produces "Cumberland Mountain Memories," a six-part radio series based on the company's first original play, Red Fox/Second Hangin'. The show originally aired in November 2002 on WMMT-FM, Community Radio, which broadcasts across eastern Kentucky, southwestern Virginia, eastern Tennessee, western North Carolina, and southern West Virginia and streams live on the internet.
2003 - Roadside and Idiwanan An Chawe premiere Zuni Meets Appalachia, a performance for children and families, at the National Museum of the American Indian in New York City and at the National Museum of American History in Washington, DC. Roadside and Idiwanan's book, Journeys Home: Revealing a Zuni--Appalachia Collaboration is awarded the Silver Addy for Excellence by the American Advertising Federation.
2004-2005 - Roadside collaborates with national and local partners to create two new plays.
- Nashville Jazz Workshop presents a workshop peformance of Betsy, a collaboration between Roadside and jazz pianist Beegie Adair. Betsy explores the intersection of jazz and bluegrass music and how the two musical traditions continue to shape our American identity.
- Roadside receives the Paul Green New Play Award for Betsy.
- Roadside playwright/composer Ron Short collaborates with community members, students, and faculty at the University of Virginia's College at Wise to compose the score for Miners and Millhands, a musical; a part of the Continental Harmonies project.
2008-2014 - Thousand Kites develops into a national criminal justice campaign project.
- Roadside collaborates with Pregones Theater to rewrite and produce Betsy in New York with three performers and a five-piece Latin jazz ensemble.
- A collaboration with “Affrilachian” poet Frank X Walker, Baltimore poet Dwayne Betts, and Connecticut poet Randall Horton results in a new play, The People's Poet, based on prisoner poet Etheridge Knight’s life and award-winning poems.
- Roadside receives the Otto Rene Castillo Award for Political Theater.
- Thousand Kites develops a partnership with an organization in the Virgin Islands protesting relocation of Virgin Island prisoners to super-maximum facilities in Roadside's home county. Kites helps them produce the Thousand Kites play and start a radio program, resulting in 125 prisoners returned to the Islands from Virginia prisons. Thousand Kites trains artists, grassroots activists, and oridinary citizens on the use of its web platform (kitescampaigns.org) and the Kites Narrative Campaign Model at five national gatherings. National criminal justice campaigns are mounted by partners in five states.
- Roadside’s Director, Dudley Cocke, participates in two meetings at the White House to discuss arts and culture policy.
- Roadside works with the Daniel Boone Wilderness Assoc. and Natural Tunnel State Park, Duffield, Virginia to create a new play, Stronger than Blood, which is the beginning of a new style of theater that combines historical reenactments, local history, and outdoor drama.
2015-2019 - Roadside collaborates with Pregones Theater to premiere and run a newly scripted production of Betsy! at the Puerto Rican Traveling Theater in NYC.
- Imagining America works with Roadside to form a Circle of Scholars, who integrate the play and related materials into their pedagogy, classroom experience, and 2015 syllibi and bring students to performances.
- Roadside partners with Appalshop's Appalachian Media Institute and Zuni, New Mexico's Zuni language theater company, Idiwanan An Chawe, to conduct a cultural exchange and collaboration between Appalachian and Zuni youth, resulting in the youth-created production The Lonely Thing.
- Roadside works with West Baltimore partners, and an oral history documenting the role culture is playing in addressing West Baltimore's issues, to create Something to Behold. The play is performed in West Baltimore's Arch Social Club and at national conferences.
- BETSY! the Concert is scripted and performed at the Appalshop Theater in Whitesburg, KY.
- Roadside works with a team of economists and students from Lafayette College's Economic Empowerment and Global learning Project and with humanities scholars from Cornell University and Imagining America to explore how artists and culture workers can join with higher education to support, enhance, and drive place-based community development. Thirteen teams of artists, scholars, and community leaders from across the US come to Appalshop to explore questions of economic development through the lens of community cultural assets.
- Roadside works with residents of multiple ages and points of view to create and perform a new play, The Future of Letcher County. Subsequent readings of the play, followed by story circles with the audience, are used by County residents as a way to address economic issues in Letcher County, Kentucky.