November 14 Is the Night Both Sides of NW Expressway Turn On the Holidays

On Saturday, November 14, at 7 p.m., Santa Claus is scheduled to appear in Heartwood Park at OAK. The trees will light up, and the Oklahoma City Figure Skating Club will skate the first performance of the season on the new rink. Directly across NW Expressway, Penn Square Mall's Santa Photos run starts the same day and continues through Christmas Eve.

So this year the busiest holiday corner in northwest Oklahoma City has one opening night, not two separate seasons. It also has a second calendar running underneath the first. Penn Square is starting a $13 million renovation, and new restaurants and stores open on a schedule that runs from mid-December into spring 2027.

OAKtober's Final Weekend Comes First

Before the holiday season starts, OAKtober, OAK's evening harvest market modeled on Europe's autumn markets, runs its second and final weekend Friday and Saturday, October 23 and 24, from 7 to 10 p.m. in Heartwood Park. The event page lists artisan vendors, food and cocktails, pumpkin painting, live floral design, leatherwork, and lantern-lit fire features after dark.

Each night has a different act. Derrick Jordan plays Friday, and Kendrik McKinney Jazz closes things out Saturday. How much you spend depends on how much of the market you want:

The free lawn music means you can hear the band from Heartwood Park without a ticket. OAK's OAKtober page has the ticket link, and INSURICA is listed as presenting sponsor.

The regular weekly events keep going after that. Live After 5, OAK's free concert series under the Cloud Trees, runs Fridays from 6 to 8 p.m. through October 30. Barre in the Park, a free outdoor class, meets Wednesday, October 28, from 6 to 7 p.m. On Halloween morning, the OAK Farmers Market runs from 9 a.m. to 1 p.m., and Junction Coffee's red double-decker bus is parked on site from 9:30 a.m. to 4 p.m.

The Rink Opens Two Days Before the Lights

OAK on Ice opens Thursday, November 12, two days before the tree lighting, and runs through Sunday, January 17, 2027. Last season ran from November 13, 2025, to January 18, 2026, so the rink stays on the same mid-November-to-mid-January schedule. The rink sits in Heartwood Park among the Cloud Trees and Cloud Puncher sculptures.

Regular hours for the 2026–27 season:

• Monday through Thursday: 4 to 9 p.m.
• Friday: 4 to 10 p.m.
• Saturday: 11 a.m. to 10 p.m.
• Sunday: noon to 9 p.m.

The weekday afternoon hours expand when local schools let out. During Thanksgiving break, November 22 through 28, the rink opens at noon every day and stays open until 10 p.m., with an 11 a.m. start on Saturday. The same schedule applies during area schools' Christmas break, December 20 through January 2. The rink is also open on Thanksgiving, on Christmas Eve from noon to 5 p.m., and on Christmas Day and New Year's Eve from noon to 10 p.m.

Admission is $18 with skate rental or $15 if you bring your own skates. OAK will sell tickets online and at the rink during open hours, and it accepts credit cards only, so leave the cash at home.

Across the Street, the Mall Starts Its Own Season

Penn Square Mall's holiday calendar starts the same weekend as OAK's. Santa Photos run November 14 through December 24. Pet Photos with Santa is Sunday, November 29, and A Special Visit with Caring Santa is Sunday, December 6. The mall also lists its Mall Walking Initiative as running all year, which is useful in January, when the rink is still open but the evenings are cold.

What's different this year is that the building is about to change. The Oklahoman reported on October 5 that Simon Property Group, the Indianapolis company that owns Penn Square, is starting a $13 million renovation at the city's oldest shopping mall. According to the paper, BHM Architects of Charlotte, North Carolina, filed the building permit on September 4. It lists new entrances, exterior repainting and signage, new corridor flooring, replacement escalators, an elevator makeover, new furniture, and outdoor landscaping. No construction phases have been published yet, so it's not clear how much of the work holiday shoppers will see.

The renovation's scope makes more sense next to the mall's history. The Oklahoman notes that Penn Square opened as an open-air mall with 582,000 square feet of retail on a 50-acre site at what was then Route 66 and Pennsylvania Avenue. Its original tenants included Street's, Rothchild's, John A. Brown, and what was then the nation's largest Montgomery Ward. New entrances and new escalators will change how shoppers enter and move through that building every day, not just during the holidays.

The New Arrivals Come One at a Time

Most of the announced openings land after the holidays. Here is what has been announced on both sides of the street, in order:

North Italia is the one opening that falls inside the holiday season. Its Oklahoma City location page gives the address as 1901 NW Expressway and shows an opening date of December 16, and Simon's Penn Square directory lists the same date. That puts its first week inside the busiest stretch of Santa Photos and four days before the rink switches to its school-break hours.

Barnes & Noble will take the longest. The Oklahoman reports that the west wing store will be the first bookstore at Penn Square since Borders closed its Waldenbooks there in 2011. It is one of three new Oklahoma stores the chain has planned. The others are a 15,000-square-foot shop in a former Joann's Fabrics in Stillwater and a store in a former Big Lots space at Yukon Village. Speaking about the Stillwater opening, CEO James Daunt told the paper the company was "very proud to restore a general bookstore to the Stillwater community."

Two more restaurant names are attached to this part of town. In its August roundup of new OKC restaurants, Visit Oklahoma City listed Culinary Dropout at OAK and J. Alexander's in Nichols Hills as upcoming first Oklahoma locations, without opening dates. Until either one sets a date, they belong on the someday list, not the December plan.

Planning a Weekend Around Both Sides

Once you know the shared schedule, a December weekend is easy to plan. Before the school break, the rink opens at 11 a.m. on Saturdays, so you can skate in the morning, walk across NW Expressway for Santa Photos, and get back to Heartwood Park when the lights come on. After December 16, North Italia gives you a dinner option on the mall side. Pet owners have one date to plan around: November 29, the only Pet Photos with Santa day on the mall's calendar.

The last week of the season comes with a firm deadline. Santa Photos end December 24, and the rink runs on holiday hours through January 2, then goes back to its regular schedule for its final two weeks before closing January 17. By May, Barnes & Noble is scheduled to open in a west wing that skaters walked past all winter.

New entrances, a new restaurant, and a bookstore on the way all affect how the NW Expressway and Pennsylvania area feels to the people who live nearby, and that kind of change shows up in home values too. If you live near this corner and wonder what your home is worth as the area changes, the team at Oberfield Real Estate Team is glad to talk it through with you. Start with a free home valuation, and we'll show you how this part of northwest Oklahoma City is moving.