Chicago

NYC to Vegas: Blues, BBQ, Cowboys & Neon

A 10-day treat-yourself run through Chicago blues clubs, Memphis BBQ, a real Montana ranch stay, and a Wyoming-to-Vegas grand finale

New York to Vegas: Chicago Jazz, Montana Wild, and the Wyoming-Utah Run

A slow-paced couple's road trip through Rust Belt diners, Chicago blues clubs, Montana dude ranches, and red-rock desert on the way to a Vegas finale

NY to Vegas the Long Way: Chicago Jazz, Montana Big Sky & Canyon Country

A slow-paced 10-day cross-country adventure — road tripping to Chicago, flying into Montana's dude ranch country, then cruising through Wyoming, Utah, and the desert to a Vegas finale

Plainfield to VOA: A Midwest Music & Eats Road Trip

5 Days from Chicagoland to West Chester, Ohio for the VOA Music Festival

Rialto to Kentwood: Route 66, the Greenwood District & the Great American Midwest

A 10-Day Solo History-Chaser's Road Trip from Southern California to West Michigan

New York to Las Vegas: The Great American Road Trip

NYC → Chicago → Memphis → Montana → Wyoming → Las Vegas — 10 Days of Music, Ranch Life & Real America

Shawshank to Acadia: A Fall Foliage Road Trip from Chicago to the Maine Coast

10 Days | Chicago → Mansfield OH → Bangor ME → Bar Harbor → Portland ME → Salem MA → Chicago

Chicago to Santa Monica: The Ultimate American Dream Loop

Grand Ole Opry · Disney World · Crab Island · Route 66 · The Pacific — 10 Days of Pure USA

Toronto to Terrace: The Great Cross-Continental Haul

5 Days · Toronto → Chicago → Twin Cities → Billings/Spokane → Surrey → Terrace, BC

Route 66: Chicago to Los Angeles — The Real American Road

15 Days of Diners, Honky Tonks, Open Highways & Genuine American Life in a Classic Convertible

Route 66: Chicago to Los Angeles — The Real American Road

10 Days, 2,400 Miles, One Legendary Highway — Two Europeans Go Full American

Toronto to Prince George: The Great American Heartland Haul

6 Days · Toronto → Chicago → Twin Cities → Badlands → Billings → Spokane → Osoyoos → Prince George

Toronto to Prince George: The Great Trans-American Road Trip

6 Days · ~3,800 Miles · Two Guys, One Tiguan, One Trailer, Zero Regrets

Toronto to Prince George: The Great North American Haul

6 Days · Father & Son Moving Road Trip · Toronto → Mount Rushmore → Osoyoos BC → Prince George

Rocky Mountain Loop: Warren, MI to the Rockies & Back

8 Days | Warren, MI → Chicago → Iowa → South Dakota → Wyoming → Colorado → Kansas → Missouri → Home

Coast to Coast USA: LA to Illinois, New England, Miami & Back

10 Days of Heartland Highways, Atlantic Shores & Southern Soul for Two

Toronto to Surrey: The Great American Diagonal — Canada to Canada via Mount Rushmore on the 4th

2,700 Miles, 8 Days, One Loaded Tiguan, and the Best Road Trip Route You've Never Planned

Father & Son Cross-Continent Blast: Toronto → Mount Rushmore → Oregon Coast → Surrey, BC

7 Days, ~3,800 Miles, Two Legends, One Epic American Road Trip

Utah's Mighty 5 & Beyond: A 30-Day Dog-Friendly Road Trip from Vermont

Arches to Zion, red rock canyons to alpine meadows — the whole magnificent show, done right, at a pace that lets it sink in

Route 66 End-to-End: Chicago to Santa Monica on Two Harleys

2,400 Miles of Asphalt, Americana, and a Las Vegas Detour