If you've driven West Will Rogers Boulevard in the past two weeks, you've probably seen the painted medallions at the Cherokee Avenue and Missouri Avenue intersections. Claremore Main Street unveiled them on Thursday, Oct. 15. The Claremore Progress placed them at those two crossings. News On 6 reported that they arrived "as the district prepares for fall and Christmas events."
The timing was deliberate. Most of downtown's holiday calendar happens on a short run of the boulevard, from the 300 block to the 500 block. Two things changed there this year: a bigger coffee shop that opened this summer, and the medallions, which went in two weeks before the first of those evenings. That first evening is tonight, Thursday, Oct. 29.
What changed on the street before the season
The medallions are the latest step in Claremore Main Street's beautification plan for the Lilac District. The Cherokee Nation provided major support, and Howell Family Eye Care also contributed. At the unveiling, Cherokee Nation Tribal Councilor Kevin Easley Jr., who represents District 14 and has practiced law downtown since 2016, told News On 6, "Claremore has always consistently punched above its weight class." Mary Ann White, president of the Claremore Main Street board, named the annual Fall Festival and Dickens on the Boulevard as the events that bring families downtown.
The other change is two doors down from the festival address. She Brews Coffee Roasters moved into a larger cafe at 408 W. Will Rogers Blvd. News On 6 reported in June that it was set to open July 1. Daily Coffee News reported in August that the new shop replaced the nonprofit's original downtown location. The separate Claremore drive-through has also closed. The menu now includes a full breakfast and lunch, drip coffee, cold brew and pastries baked in-house. The extra space also gives She Brews more room for its job-training program for women leaving incarceration.
Some online directories still list She Brews at its old 414 address. She Brews' own page gives 408, with hours of 6 a.m. to 5 p.m. Monday through Saturday, closed Sunday. Those hours shape the evening events below. The cafe closes an hour before each of the 6 p.m. downtown events begins, so get your coffee in the afternoon.
The season, by date
Two organizations run the downtown part of this calendar. Claremore Main Street runs the boulevard evenings, and the Claremore Chamber of Commerce runs the shopping promotion and the parade. The Halloween events come from the city's museums and other hosts.
| Date | Event | Time | Where | Organizer |
|---|---|---|---|---|
| Thu., Oct. 29 | Fall Festival | 6–9 p.m. | 422 W. Will Rogers Blvd. | Claremore Main Street |
| Fri., Oct. 30 | HotRod Trunk or Treat | 6:30–8 p.m. | Claremore Expo parking lot | Listed on Visit Claremore |
| Sat., Oct. 31 | Hocus Pocus Halloween | 1–4 p.m. | Claremore Museum of History, 121 N. Weenonah Ave. | Claremore Museum of History |
| Sat., Oct. 31 | Halloween at the Museum | 6–8 p.m. | Will Rogers Memorial Museum, 1720 W. Will Rogers Blvd. | Will Rogers Museum |
| Sun., Nov. 1 | Shop Local! Santa Cash begins | All season | Participating local businesses | Claremore Chamber of Commerce |
| Fri.–Sat., Nov. 20–21 | Dickens on the Boulevard | 6–9 p.m. both nights | 422 W. Will Rogers Blvd. | Claremore Main Street |
| Sat., Dec. 12 | Claremore Christmas Parade | 6–7:30 p.m. | Eastbound on Will Rogers Blvd. from the Expo Center | Claremore Chamber of Commerce |
The Main Street events share one address, 422 W. Will Rogers Blvd. Tonight's Fall Festival and both Dickens nights are listed there. Halloween is the one weekend that moves off that stretch.
Tonight at 422, and why Halloween weekend happens elsewhere
The Fall Festival runs from 6 to 9 p.m. tonight. The city's calendar files it under family fun, festival, holiday, outdoors and shopping. Because it falls on a Thursday, it opens the downtown season two days before Halloween, not on Halloween weekend itself.
The city calendar shows no trick-or-treat on the downtown boulevard this year. The weekend events are spread out instead:
- Friday, Oct. 30: the HotRod Trunk or Treat in the Claremore Expo parking lot, 6:30 to 8 p.m.
- Saturday afternoon, Oct. 31: Hocus Pocus Halloween at the Claremore Museum of History on North Weenonah, 1 to 4 p.m., with candy stops, a scavenger hunt, a basement haunted house, snacks and crafts.
- Saturday evening, Oct. 31: Halloween at the Museum, where local businesses and organizations hand out treats at Will Rogers Memorial Museum from 6 to 8 p.m. Admission is free.
The Saturday-night event is still on Will Rogers Boulevard, but at 1720 West, the far west end, well away from the medallion blocks. October 31 is also the morning of the Will Rogers Days Parade, listed for 10 to 11 a.m. That makes Saturday a full day, starting with the parade in the morning and finishing with treats at the museum that evening.
Santa Cash fills the weeks between festivals
There are three weeks between Halloween and Dickens with no evening events downtown. The Chamber's Shop Local! Santa Cash campaign covers that stretch. It starts Sunday, Nov. 1. Shoppers get a ticket for every $10 spent at a participating local business, and the campaign ends with a live drawing for $17,500 in cash prizes at Cherokee Casino Will Rogers Downs.
The participating retailers named on the 2026 listing include:
- Kiley's Kloset, 10Box Cost Plus, 6:19 Nutrition and Nabatak Outdoors
- Bennett's Route 66 Pharmacy and J&J Pharmacy and Gifts
- Bill & Ruth's, Reasor's, Walke Meat Company and Stillwater Milling
- Armstrong Bank, BancFirst, RCB Bank and TTCU
- Sooner Flooring & Design, Helt Heating & Air and Suburban Chevrolet
- J.M. Davis Arms & Historical Museum, Visit Claremore, Collective Kitchens at Will Rogers Downs, Claremore Children's Center and Claremore Eye Associates
The listing does not give a drawing date or the full 2026 contest rules. Check with the Claremore Chamber at claremore.org before counting on last year's terms.
Dickens fills the 300 and 400 blocks for two nights
Dickens on the Boulevard runs two nights this year, Friday, Nov. 20 and Saturday, Nov. 21, from 6 to 9 p.m. each night. Last year's city listing showed a single date, Nov. 22, 2025. The 2026 listing asks guests to celebrate "Victorian Style" and dress up. It promises music, a street dance, food, games, decorated shop windows, hot cocoa and Santa at 320 on Main.
Three Twenty on Main is an event venue at 320 W. Will Rogers Blvd. That puts Santa a block from the festival address. Here's what sits along the walk between the Santa line and the festival address, using addresses from Visit Claremore's dining directory and the Claremore Chamber's 2025–2026 guide:
- 300 block: Boomarang Diner at 302 and Dot's Café at 310. Thrift Harbor at 316 and Rhapsody Boutique Salon and Spa at 318 sit next to the venue, and Freckled Finch at 321 and Crooked Roots at 323 are across the street.
- 400 block: She Brews at 408 and the festival address at 422.
- 500 block: The Same Page bookstore at 514, which the Tulsa Flyer listed as a stop on its regional bookstore crawl in April 2026, and Gibby C's South in Your Mouth at 520.
- Around the corner: Main Street Tavern at 116 N. Missouri Ave., just north of the Missouri Avenue medallion.
Dickens shopping also counts toward Santa Cash, as long as the store is a participating business.
The parade comes in from the Expo end
The season ends with the Chamber's Claremore Christmas Parade on Saturday, Dec. 12, from 6 to 7:30 p.m. The route heads east on Will Rogers Boulevard from the Claremore Expo Center. That puts the season's last event on the same boulevard as the Fall Festival, the Halloween treat stop at the museum and both Dickens nights.
Neokla Legacy Group is a hometown team in northeast Oklahoma, and Claremore's downtown is part of the community we serve. If you're thinking about a home within walking distance of the Lilac District, or you'd like to talk about the blocks around Will Rogers Boulevard, Neokla Legacy Group is glad to help. Let's get started.
