The Madonna of the Trail stands in the Euclid Avenue median facing south, toward the corner where Euclid crosses Foothill Boulevard. She was dedicated on February 1, 1929. That same year, farther west on the same road, Ed and Louise Haefner, who came from Buffalo, New York, opened a small roadside restaurant. It would become the Buffalo Inn.
In 2026 Route 66 turns 100, and those two 1929 landmarks are headed in different directions. The Madonna is a civic emblem, one of 12 such monuments in the country, and Upland worked hard to win her. The Buffalo Inn is closed and on a Planning Commission agenda, with 72 condominiums proposed for its site. Upland is celebrating the centennial by giving the pavement a new start. The buildings along that pavement, the ones that make a stretch of road recognizable as Route 66, are being decided one hearing at a time.
What the City Rebuilt Under the Old Road
Anyone who has driven Foothill west of Euclid over the past year has lived with this project. Its official name is the Foothill Boulevard Pavement Rehabilitation & Utility Improvements Project, and it runs from Benson Avenue to Euclid Avenue. City Council awarded the $13.2 million contract to Gentry Brothers Inc. on June 23, 2025, and construction started in October 2025.
Much of the work is underground or at the curb, so a driver may never notice it. The project covers asphalt reconstruction and resurfacing, new water mains and service lines, sidewalks, curbs, gutters, curb ramps, driveways and cross gutters. The parts you can see are landscaped center medians, buffers along the bike lanes, fresh striping, upgraded traffic signals and better lighting. The money came from several sources. San Bernardino County Supervisors Curt Hagman and Jesse Armendarez put in $4 million of discretionary funds, and the rest came from Upland's water and sewer funds, the gas tax, ARPA and RMRA dollars.
The schedule has been a moving target. The city's project page listed an October 2025 to August 2026 window, and its capital projects index still shows the job under construction rather than completed. The city's latest word is its centennial event page, which says the October 3 celebration will "highlight the much-anticipated reopening of Foothill Boulevard." Residents can plan around that date. It is not an engineering sign-off, and the last median plantings or signal adjustments may still be underway afterward.
A Drive East From Central Avenue
The rebuilt pavement matters because of what sits along it. The California Historic Route 66 Association names four points of interest in Upland. Add the storefronts that have opened or held ribbon-cuttings this year, and a drive east from the Montclair side covers most of the corridor's history in a few minutes:
- The former Buffalo Inn, 1812–1816 W. Foothill Boulevard. It sits on 4.42 acres near Central Avenue. It has been closed since 2015.
- The Golden Arches McDonald's, 1590 W. Foothill. The association lists it as a classic arches site.
- The Big Coffee Cup sign, 1013 W. Foothill.
- Red Devil Pizza, 907 W. Foothill. Its Upland Chamber grand-opening ribbon-cutting is set for Wednesday, September 23, at 5 p.m.
- Upland Pizza Company, 121 W. Foothill. It is just west of Euclid, and the Chamber cut its ribbon on July 1, calling it one of Upland's newest dining spots.
- Madonna of the Trail, Euclid Avenue at Foothill. The association gives her address as 1010 Euclid Ave.
- The McDonald's double arches, 100 E. Foothill.
- Charleys Cheesesteaks & Wings, 1398 E. Foothill. It held its Chamber ribbon-cutting on July 21.
Most of that list has something in common. The historic stops are signs, arches and a statue, the kinds of things that last because they are small and easy to keep. The only full building from Route 66's early years is the first stop on the drive.
The Hearing Before the Celebration
The proposal for the Buffalo Inn site is called the Buffalo Grove Specific Plan. It calls for 72 detached condominium units, and the Colorado-based developer is Century Communities. The review has moved slowly so far:
- July 22, 2026. The Planning Commission adopted no resolutions and continued the hearing to August 26 over sewer and other technical issues.
- August 26, 2026. City staff said the sewer connection was still unresolved and asked for more time to work with the applicant. The commission voted 6-0 to continue again.
- September 23, 2026. This is the continued hearing. At this stage the commission is asked for a recommendation to City Council, not a final decision.
The historic record is also in dispute. A Historical Archaeological Resources Report cited in the city staff report found that the buildings did not qualify for individual historic designation. They keep some of their architectural character, but they were heavily altered in the 1970s and 1980s. At the August hearing, a public commenter challenged that survey. He said local preservation groups were never consulted, asked for an independent third-party peer review, and named the California Historic Route 66 Association as a regional advocate for keeping the site.
The most visible advocate has been Gil Caughman, who runs the Black Bell Project. The project marks surviving Route 66-era buildings in California with a small black bell and encourages people to visit them. He described the site to the Daily Bulletin in July:
"I can't imagine anything that's more historic in Upland than the Buffalo Inn in terms of Route 66. I mean, the building was established for that purpose alone. It's got the whole story behind it."
The inn's own history is layered. The Haefners leased the space out in 1939, and it went through several restaurants and bars before it took back the Buffalo Inn name. Caughman remembers it as a place to hear bands and order the buffalo burgers it was known for. It was saved from auction in 2017 and has sat quiet since then.
The city's notice for the September 23 hearing describes it as a step toward a recommendation to City Council, so the council's decision comes later. The city's party for the road on October 3 falls ten days after that hearing.
The Centennial Weeks, Day by Day
For residents, the plan for the next few weeks is simple, and several deadlines come up quickly.
Tomorrow, September 23, is the registration deadline for both the Classic Car Display and the Cardboard Car Showcase. The cardboard contest is open to kids 12 and under. Voting starts October 3, and winners will be announced October 14. The same evening brings the Red Devil Pizza ribbon-cutting and the continued Buffalo Grove hearing.
Now through October 16, the city's Road Trip Challenge sends residents along Foothill to collect stamps at participating businesses. An extra "Fuel Up" stamp with a purchase adds entries to bonus drawings, and winners will be announced October 19. The city's event page doesn't name the participating businesses, so start by picking up a map. Maps are available at the participating locations and at four city sites:
- Upland City Hall, 460 North Euclid Avenue
- Gibson Senior Center, 250 North 3rd Avenue
- Magnolia Recreation Center, 651 West 15th Street
- Landecena Community Building, 1325 San Bernardino Road
Saturday, October 3, the Route 66 Centennial Celebration runs from noon to 5 p.m. at Memorial Park. Admission and parking are free. Vendors and activities open at noon, the classic cars and local youth performances start at 12:15, and the Cherry Bomb Revival Band plays at 2:15. You may bring your own food and non-alcoholic drinks, coolers up to 50 quarts, chairs and blankets. Open flames and grills are not allowed. The Saturday Upland Farmers Market and Craft Faire runs that morning from 9 a.m. to 2 p.m. at 2nd Avenue and A Street, so you can walk the market downtown before heading to the park.
The Road Trip Challenge and the drive east from Central Avenue fit together well. Starting at the Buffalo Inn site and ending at the Madonna takes you past most of what this post has covered, from the 1929 building still under review to the 1929 statue that is secure.
A Note From Our Office
Our team works out of Rancho Cucamonga and brings more than 37 years of brokerage and appraisal experience to Upland and the surrounding foothill communities. When a corridor like Foothill changes, whether through a city project or a proposal like Buffalo Grove, homeowners nearby deserve a value estimate backed by documentation. If you want a clear read on your home's value as Foothill reopens, The Mowery Group is available to help. Schedule Free Consultation.
