Full disclosure: I never played The Oregon Trail videogame. Not being much of a gamer (except for my Pac Man and Ms Pac Man obsession in the ‘80s), I actually never heard of the game. If you had asked me what was The Oregon Trail, I might have guessed something that fur traders used to get from the Midwest to the Pacific Ocean. So color me surprised that it turned out to be a pretty thoughtful, pretty funny show now onstage at the Alleyway Theatre.

Renee Landrigan is Jane, a typical ‘90s middle schooler who dramatically flops herself on the floor in embarrassment, dials up her mom on a flip phone with an antenna, and can’t quite keep up with big sister Mary Ann (Sue McCormack). Jane has a secret crush on class hunk Billy (Ben Caldwell) and another secret: a disc that sends her imagination back a century to The Oregon Trail where she can pretend she’s packing the covered wagon for a ride across the prairie, circa 1848. It’s all pretty harmless fun….until the day the computer talks back to her.

The stage action cleverly shifts between today Jane and 1848 Jane (maybe her great great grandmother, perhaps) with Elise Vullo in the vintage Jane role. Jane from the days of yore is struggling with her mother’s death and her father’s decision to go west. She adores her accomplished older sister Mary Ann (McCormack in a bonnet) who has stepped up into the caregiver’s role. But then Jane struggles with the rough, slow road and the threat of death by dysentery and other things. We time-hop forward and today Jane is an adult, of sorts. She is struggling to find her place in the world while big sister Mary Ann has a tiring but rewarding medical career. Jane manifests classic signs of depression, not caring for herself, devoted to screens (both computer and TV), unable to hold a job or find a career pathway. Tough love doesn’t seem to work. Even a chance meeting with ex-crush Billy isn’t shaking her out of her reverie. Mary Ann decides a wilderness day, some sage to burn, and some journaling might help Jane find her path.

Landrigan is a delight as Today Jane, both  young and grown up. She’s a great twitchy ‘tween and a lost soul 20-something. McCormack’s Mary Ann is equally solid: as today’s Mary Ann she’s both weary and wise and just wants her kid sister to find her way. Caldwell’s Billy is the middle school jerk who hasn’t grown up (we all know him). It’s John Profeta as Clancy, the 1848 dad and Nicholas Lama as the voice of the game who provide the wisdom of the Trail….actual and electronic. Profeta is determined that he’s made a good decision to ford the streams and hike the hills to a new life for his family. Lama’s resonant voice reminds us that outside forces can oddly, wickedly control you when you least expect it. It’s a clever device by playwright Bekah Brunstetter. Director Chris J Handley and Tim McGrath, scenic designer made good use of the stage that took use from classroom to wilderness to the gals’ apartment. Todd Warfield had some work cut out for him sourcing a full size-looking wagon and some ancient greige computers (memories of my vintage 286!) I loved some of Nicholas Quinn’s music choices for audio transitions, too.

All told, the earlier scenes and the waaay earlier flashback scenes were more satisfying than the ending. I would have liked to have seen a glimpse of Today Jane and Yesteryear Jane one more time, and maybe heard more creepy shout outs from the game himself to knit it all together.

The Oregon Trail is onstage to May 28. It runs a solid two hours+ with an intermission to enjoy Alleyway’s lovely lobby.  Get tickets and info at www.alleyway.com. Bring a mask. You’ll be OK.