The Route 66 centennial day

Start at the west bookend, where travelers have eaten since the 1840s — stagecoach traffic first, Route 66 traffic later, you now. The dining room doesn't open for breakfast; this is a walk-up-and-look stop, and the moment to book tonight's table if the day ends in dry-aged steak. The building wears its century and a half honestly, and on a weekend the reservation is not optional.

A pocket park on the historic alignment that's honest about its job: themed signage to look at while you stretch, free parking, and a clean access point onto the Pacific Electric Trail. Walk a stretch of the old Red Car right-of-way that shadowed the highway — two pieces of transportation history in one short stop. It's small and knows it; twenty minutes is plenty.

Red-sauce Italian in portions calibrated for teenagers after practice, anchoring this stretch of Foothill since 1984 with family roots on the route older than that. Order the meat sauce, accept the garlic bread as mandatory, and split plates without shame — locals do. On the road's food spectrum this is the counterweight to the Sycamore's white tablecloths: zero pretension, maximum comfort, cheap.

East to the corner where the vineyard era and the highway era overlap: California Historic Landmark No. 490, where the state's first commercial winery vines went in back in 1839. It's a retail plaza now — nobody's pouring wine — but the plaque, barrels, and Route 66 signage are free and outdoors, and Klatch Coffee's flagship shares the plaza. Order the 2026 Centennial espresso: a hometown world-champion roaster toasting the road its shop sits on.

The anchor of the whole day: a c.1915 filling station that was pumping gas when the road out front became Route 66 in 1926, restored by volunteers and on the National Register since 2018 as the last of its design on the California alignment. The museum inside is small, dense, free, and staffed by people who know the road cold. Open Thursday–Sunday 10–4, with hours that can flex — call (909) 271-1024 — and a donation box that funds the restoration.

Continue east for the five-minute landmark: the 1908 Mission-style bell tower of the old Virginia Dare Winery, standing over an office plaza. Nothing to tour, no door to knock on — you photograph a handsome century-old tower and move on. It completes the windshield tour of what this valley was when the highway arrived: the largest wine region the road ever drove through.

In 1920 the Cucamonga Valley grew more wine grapes than Napa and Sonoma combined, and the family farming what's left of those vines runs this winery in Mira Loma, fifteen minutes south — established 1927, on the National Register, pouring old-vine Zinfandel from dry-farmed, own-rooted vines and a Three Friends Port that's taken more international golds than any tawny in America. Call (951) 685-5376 for current tasting room hours before you commit the detour.

Drive back west for the finale, timed to full dark: the neon Aladdin lamp shooting a real flame into the sky over Foothill — the best surviving piece of roadside theater on this stretch of 66 and the most photographed object in the city. The dinner house behind it reopened in late 2024 after a full renovation; take a drink at the bar at minimum, or head a half-mile west to the Sycamore table you booked this morning.