"Many visitors also enjoyed the Entertainment Zone, which allowed them to responsibly enjoy a beverage while strolling through participating businesses and experiencing everything our historic downtown has to offer." That's how Councilman James Breitling described July's 2nd on 2nd in a post on The Upland Update. He added that the event "returns" monthly.
The October edition falls on Saturday, Oct. 10, and the date matters. Second Saturday is still a Saturday. The same stretch of Second Avenue that hosts 2nd on 2nd at night is already closed every Saturday morning for the Farmers Market & Craft Faire. So Second Avenue changes hands three times that day: market, then cars for a short window, then pedestrians again after dark.
Two closures, one block
The City of Upland's downtown page lists both closures. The Upland Farmer's Market and Craft Faire runs every Saturday from 9 a.m. to 2 p.m. at Second Avenue and A Street. Street closures run from 6:30 a.m. to 3:30 p.m. on Second Avenue between A Street and Ninth Street, and on A Street from Second Avenue to Third Avenue. The city's listing mentions crafters, family activities, and that pets are welcome. The downtown association's events page adds produce, baked goods, and plants.
2nd on 2nd is run by Historic Downtown Upland, Inc. The city describes it as an outdoor dining event with live bands, local talent, and vendors on the second Saturday of each month, centered at Second Avenue and Ninth Street. According to the downtown association's October listing, Second Avenue goes pedestrian-only from 5 to 10:30 p.m. on Oct. 10. Guests 21 and older can buy drinks and carry them within the designated Entertainment Zone.
Lined up, the closures cover most of the day:
- 6:30 a.m. City closure on Second Avenue between A and Ninth streets begins.
- 9 a.m. to 2 p.m. Farmers Market & Craft Faire.
- 3:30 p.m. The posted market closure window ends.
- 5 p.m. to 10:30 p.m. 2nd on 2nd, with Second Avenue pedestrian-only and the 21+ Entertainment Zone active.
The gap between 3:30 and 5 p.m. is about 90 minutes. Neither event listing spells out the full closure limits or parking for event night, so give yourself extra time if you drive in for the evening.
What stays open from the market to the Entertainment Zone
Two downtown businesses post hours on their own websites that cover both ends of the day. Rad Coffee at 232 N. 2nd Ave. lists daily hours of 6 a.m. to 10 p.m. It opens before the market setup and closes half an hour before 2nd on 2nd ends. Kings Brewing at 296 N. 2nd Ave. lists Wednesday through Sunday hours, so it's open on a Saturday.
Beyond those two, the best recent address list for the block is the Upland Lemon Festival's participating-business roster from June 2026. It confirms that these places were on Second Avenue this year. It doesn't confirm October hours, so check a business's own page before you plan a meal around it.
| Address on N. 2nd Ave. | Listed on the 2026 Lemon Festival roster |
|---|---|
| 151 | Barcuso |
| 152 | 2nd Avenue Boutique |
| 161 | La Michelada |
| 181 | Cookies n Pints |
| 186 | Allegro |
| 188 | Blessed Fyah Culture Shop |
| 228 | Cosmic Bakery |
| 250 | A World of Decor |
| 260 | Heart Pop |
| 263 | Empire Skates |
| 291 | JD Allison's Bar and Grill |
Antique Alley at 257 E. Ninth St. also appears on that roster. It sits right at the corner where 2nd on 2nd is centered.
On the roster, the 100 block clusters food and drink: Barcuso, La Michelada, Cookies n Pints, and Allegro all sit between 151 and 186. The 200 block leans toward shops, with Cosmic Bakery at 228, A World of Decor, Heart Pop, and Empire Skates, then JD Allison's at 291 and Kings Brewing at 296. A loop from the market at A Street north past Ninth covers all of these on foot.
No published source names which businesses join the Entertainment Zone on a given night. Breitling's July post describes the participants as downtown restaurants, bars, breweries, and other small businesses, without a list.
The midday option is three miles of Route 66 away
Oct. 10 also brings a third event that fills the hours between the two closures. Garage Rods for a Cure, a car and motorcycle show benefiting the American Cancer Society, runs from 10 a.m. to 4 p.m. at Cable Airport, 1749 W. 13th St. Spectators get in free, according to the Daily Bulletin.
The show ends 30 minutes after the market closure window. That leaves time to get back downtown for the 5 p.m. start, with the whole day running on published hours.
Why the car crowd is warmed up already
Oct. 10 is the second car-heavy Saturday in a row. Today, Oct. 3, the city is holding its free Route 66 Centennial Celebration at Memorial Park from noon to 5 p.m. It marks 100 years of the Mother Road and what the city calls "the much-anticipated reopening of Foothill Boulevard." The schedule includes a classic car display starting at 12:15 p.m. and the Cherry Bomb Revival Band at 2:15 p.m. Kids 12 and under can enter a cardboard car showcase, with voting starting today and winners announced Oct. 14.
The reopening follows the city's $13.2 million Foothill Boulevard rehabilitation from Benson Avenue to Euclid Avenue, scheduled for October 2025 through August 2026. The project notice lists resurfacing, water pipelines, sidewalks, traffic signals, enhanced lighting, landscaping, and bike lane improvements. It credits $4 million in discretionary funds from San Bernardino County Supervisors Curt Hagman and Jesse Armendarez. The city hasn't published a list of which upgrades are finished, so expect the street to match the project list in most places, though maybe not every block yet.
The corridor's Route 66 landmarks are still in place. The California Historic Route 66 Association lists the Madonna of the Trail at 1010 Euclid Ave. and the Big Coffee Cup sign at 1013 W. Foothill Blvd. The cup sits at the curb on the north side of the road, in front of a Starbucks. The Madonna, a pioneer-mother monument at the Euclid and Foothill intersection, was dedicated on Feb. 1, 1929. The city is also running a Route 66 Road Trip Challenge, with stamps collected at participating Foothill Boulevard businesses. The event page doesn't name those businesses, so check with the city before you start.
Today puts the attention on Foothill. Next Saturday it moves a few blocks to Second Avenue, which may be the busiest single day the downtown block has this fall.
Hours shift from month to month
2nd on 2nd doesn't keep the same hours every month. The city's September listing ran from 5 p.m. to midnight on Sept. 12. October's listing ends at 10:30 p.m. One downtown business's event page described the series as a second-Friday-and-Saturday weekend through September. For Oct. 10, go by the October listing on downtownupland.org, which gives Saturday only, 5 to 10:30 p.m.
The rest of downtown's fall calendar
After Oct. 10, the next few events are closer together, and two of them return to the same blocks.
| Date | Event | Where | Hours |
|---|---|---|---|
| Fri., Oct. 16 | Monster Mash-Up Movie Night, free and all ages | Magnolia Park | 5 to 8:30 p.m. |
| Sat., Oct. 24 | Scary-A-Faire, free, with trick-or-treating and community booths | Historic Downtown Upland | 4 to 8 p.m. |
| Sun., Nov. 1 | Día de los Muertos Festival, free, with live music, food trucks, a kids' zone, and a community ofrenda | Downtown Upland | Noon to 8 p.m. |
| Fri., Nov. 13 | Fall Puzzle Palooza | City listing | See city page |
| Thu., Nov. 26 | 19th Annual Turkey Trot | City listing | Thanksgiving morning |
Scary-A-Faire also lands on a Saturday. Its 4 p.m. start comes 30 minutes after the market's posted closure window ends, so the city's special events page is the place to confirm details closer to the date. Día de los Muertos falls on a Sunday, so it's the one downtown festival this fall that doesn't share a day with the market.
If a day on Second Avenue has you wondering what downtown homes are worth now, or whether one would suit your needs, I'm happy to talk it through. I'm Sherri Lopez, and I can put together a free home valuation or an Upland neighborhood guide with the downtown blocks in it, and help you work out what fits.
