Jan 17, 2026
Route 66
Route 66: Chicago to Santa Monica Route 66 isn’t just a road — it’s a rite of passage. Stretching roughly 2,4...
Read the guide →Road Trip Guides
New guide every Monday — all of our published trips appear here automatically.
Jan 15, 2026
Route 66 Road Trip Guide
Route 66 is America’s most iconic road trip, stretching from Chicago to Santa Monica through historic towns, classic diners, and unforgettable roadside stops. This guide covers when to go, must-see highlights, and why the Mother Road remains a bucket-list drive.
The Best U.S. Road Trip Ideas
The best road trips aren’t just about where you’re going — they’re about the moments you collect along the way. From legendary highways and national park loops to scenic coastal drives, this guide highlights the most memorable road trip ideas across the United States.
Each week, we publish a new in-depth road trip guide to help you plan, explore, and remember the journeys worth taking.
Explore Personalized Road Trip T-Shirts New road trip released every Monday
This Week’s Featured Road Trip
Route 66 — The Mother Road
A legendary cross-country drive from Chicago to Santa Monica, filled with neon signs, classic diners, and historic roadside stops that define American road travel.
Read the Route 66 Road Trip Guide →
Shop Route 66 Road Trip T-Shirts →
Published Road Trip Guides
This list grows weekly as new road trip ideas are released.
Why Road Trips Are Worth Remembering
Road trips often mark meaningful moments — family vacations, graduation trips, retirements, reunions, or bucket-list adventures. Long after the bags are unpacked, it’s the shared stories and miles traveled together that stick.
Many travelers choose to commemorate their journey with a personalized road trip t-shirt designed around the places, people, and year that made the trip theirs.