Book Review: Vertical: Passion and Pinot on the Oregon Wine Trail

Reviewer’s Note: Review copy of the book discussed here was provided to me at no cost in exchange for my honest opinion.

In Vertical, the sequel to his cult favorite wine novel Sideways, author Rex Pickett takes readers back on the road with best friends and habitual drinkers Miles and Jack. Set against the lush backdrop of Oregon Pinot Noir wine country, this road trip finds the duo heading from California to the International Pinot Noir festival, this time bringing Miles’s ailing mother along for the ride.

The book title functions as a fair description of the path Miles Raymond’s life has taken since the events of Sideways, back when he and Jack Cole were, respectively, a rudderless aspiring writer and a charismatic, though past-his-prime, actor. Now over 40, and having achieved a degree of writing success that he could never have expected, an ascendant Miles feels somewhat validated, but grapples with feeling deserving of that validation, and with the human aspects of his star having risen at last. In between the wine-soaked speaking engagements and meaningless trysts now filling his hours, this Miles has achieved a measure of clarity about self-defeating tendencies that still plague his opinion of himself and his dealings with the opposite sex.

Recognizing his foibles and taking active measures to alter them are two different things, however. Learning new tricks does not come easily to this aging dog, especially with his newfound wine world celebrity providing him a steady diet of experiences that speak directly to his vices, and his lifelong partner in debauchery, Jack—now divorced from the bride he wedded at the end of Sideways—in tow. Factor into that equation a frail souse of a mother and a relationship between her and her cannabis-smoking caretaker growing more strained with every mile put behind them, and circumstances come close to justifying some of Miles’ indulgences (if only as flailing stabs at sanity-mooring through fleeting escapism), making it impossible not to feel for him and want to protect him from himself.

This second book in the Sideways Trilogy leaves no emotional chord unstruck as the friends make the journey to deliver Miles’s mother from a dismal California nursing home to live with her sister in Sheboygan, Wisconsin. Pickett’s adroitness at shifting tone between hilarious and heartbreaking keeps the characters likeable even at their most misguided. The author’s ability to wring modicums of humor—black though it may be—from even the most harrowing scenes pulls readers close in almost conspiratorial fashion. It lends voice to the kind of impolitic thoughts we’ve all had during a stressful moment where we needed to find a reason to laugh in order to keep from screaming.

As for Miles and Jack, they remain much the same two guys we met in Sideways, and yet they’re different enough this time around—owed in large part to where the story finds each of them in life regarding success and relationships—to make this trip new and exciting, never feeling like a rehash of their Santa Ynez adventures. Jack is still incorrigible, yet protective of his buddy. Miles’ affinity for using complicated words still elicits eye rolls from those around him. The wines and the regions where they are found still get described with a poet’s reverent affection, in language that will have readers reaching to pour a glass of their favorite vintage as they share this oenophile’s holiday with familiar friends and get to know new ones.

Vertical is a delicious blend of comedy, drama, road trip tale, and enthusiastic paean to wine love. It is also a touching and personal portrait of a man coming to terms with a loneliness that wine and fame will never remedy. Readers who enjoyed their first outing with Miles and Jack will no doubt be glad to ride shotgun on this next adventure.

Learn more about Rex Pickett’s Vertical at

Paperback: 416 pages
Publisher: Loose Gravel Press
ISBN-10: 0997545909
ISBN-13: 978-0997545906

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