The Brookside Business Association has given its holiday tree lighting a new night. For 2026, the lighting moves to Friday, November 13. The cocktail crawl stays on Thursday. Then the retail shops add four more Thursday evenings of extended hours, running through December 17. Count them and Brookside's holiday season comes to five Thursday evenings, one Friday, and two Saturdays. Most of the season happens after work.
That fits how the association schedules the rest of its year. The 2026 Brookside events calendar also put the Sweetheart Sip & Shop on a Thursday in February, Patio Fest on a Thursday in June, and the fall Sip & Shop on a Thursday in September. In this district, Thursday evening is the usual time for a shopping event. The holiday season just adds more of them in a row.
The Full Calendar, in Order
Here is every holiday date the Brookside Business Association has posted for this season, as listed on its Holiday Season Opener page and its 2026 events calendar:
| Date | Event | Hours |
|---|---|---|
| Thursday, Nov. 12 | Holiday Spirits, a Brookside cocktail crawl | 5 to 8 p.m. |
| Friday, Nov. 13 | Holiday Tree Lighting | 5 to 8 p.m. |
| Saturday, Nov. 14 | Cookies, Cocoa & Crafts | 11 a.m. to 2 p.m. |
| Thursday, Nov. 19 | Extended holiday shopping hours | Evening |
| Saturday, Nov. 28 | Small Business Saturday | Listed on the calendar |
| Thursday, Dec. 3 | Extended holiday shopping hours | Evening |
| Thursday, Dec. 10 | Extended holiday shopping hours | Evening |
| Thursday, Dec. 17 | Extended holiday shopping hours | Evening |
The extended Thursdays skip Thanksgiving week, which is why there's a gap between November 19 and December 3. Retail businesses are the ones offering the late hours. If a particular store is on your list, check its own hours before you head over.
Why the Friday Move Matters
In past years the cocktail crawl and the tree lighting were part of the same opening weekend. With the lighting on Friday, the three days of the opener now serve three different crowds. Thursday's Holiday Spirits is for adults. The association describes it as festive sips and shopping specials at participating retailers, plus food and drink promotions at participating restaurants. Saturday's Cookies, Cocoa & Crafts is for families with kids, held midday at participating businesses.
Friday is for everyone, and it has the most detailed schedule of the three nights. Everything happens on the plaza next to BKS Nails at 6246 Brookside Plaza:
- 5 to 6 p.m.: live music by students from heARTbeat studio
- 6 p.m.: the Brookside holiday tree lighting
- 6 to 7 p.m.: a brass band
Kids can write letters to Santa and look for him around the plaza. Cookies, coffee, and cocoa are served while supplies last. The lighting is at 6 p.m. and the event runs until 8, so families can catch the tree and the band and still get to dinner nearby.
Two Blocks Hold Most of the Stops
Thursday evenings work in Brookside because the participating shops sit close together. According to the association's shop directory, one stretch of West 63rd Street, the 300 block, has a run of independent storefronts that you can walk end to end in a few minutes:
- Brookside Jewelry, 306 W. 63rd St., jewelry and repairs
- LADYCO, 314 W. 63rd St., Suite A, women's clothing in sizes XS through 3X
- STUFF, 316 W. 63rd St., handmade art and lifestyle goods
- Jorjy, 320 W. 63rd St., home and lifestyle
- Lauren Alexandra, 322 W. 63rd St., baby clothing
- Leopold Gallery + Art Consulting, 324 W. 63rd St., regional art
- EB and Co., 326 W. 63rd St., accessories
- The Grove Spa & Boutique, 328 W. 63rd St., skincare and boutique goods
- Brookside Toy & Science, 330 W. 63rd St., a mom-and-pop toy shop
The second cluster is on Brookside Plaza near the tree. The Corner Candleshop at 6231 Brookside Plaza is a neighborhood candle-maker. Shop Local KC at 6245 Brookside Plaza sells gifts and flowers and runs a marketplace for more than 300 Kansas City artisans. Sierra Winter Jewelry, at 6245 Brookside Blvd., sells handcrafted pieces. All three are within a short walk of the lighting spot at 6246.
Some businesses have been here a long time. Gerry Optical at 122 W. 63rd St. has served Kansas City since 1912, according to the directory. EB and Co. is much newer. In October 2025, Startland News reported that it was celebrating five years in Brookside, and described its Kansas City-themed accessories and its charm bar. A charm bar is a good gift stop on an extended-hours Thursday, since you can put a gift together yourself.
The Dinner Hours Line Up
An evening of shopping usually ends at dinner. This year, Brookside's newest restaurant is open on the same nights as the holiday events.
Disco Burger started as a food cart outside Varsity Club in the River Market. It opened its first brick-and-mortar restaurant at 600 E. 63rd St. in late August, with indoor dining, a patio, and a takeout window, according to The Kansas City Star. Its posted hours are 4 to 10 p.m. Wednesday and Thursday, 4 to 11 p.m. Friday and Saturday, and 11 a.m. to 3 p.m. Sunday. That covers all five Thursday evenings and the Friday tree lighting.
Co-founder Matt Chapman told The Kansas City Star why the restaurant ended up in Brookside:
"I think we noticed early on through our pop-ups in the Crossroads, (Brookside) was a demographic that seemed to travel lots to the Crossroads and a lot of them came to be our early followers who appreciated the brand, the food, and they seemed to really vibe with us. So we thought, why don't we just put it down in their neighborhood."
The Brookside menu goes beyond the cart. The Star reported a Denver steak au poivre for $30, a pickle Caesar for $10, the double disco burger for $12, and soft serve for $5, along with a cocktail list and a natural wine program. Chapman also told the paper the kitchen plans to change items with the seasons.
Other restaurants are closer to the tree. The 6300 block of Brookside Plaza alone has Carmen's Café at 6307, Jalapenos Mexican Restaurant at 6318, Sayachi Sushi at 6322, Red Door Woodfire Grill at 6324, and Brooksider Sportsbar & Grill at 6330, according to the association's restaurant directory. On West 63rd, Cru Bistro & Bottles at 128 W. 63rd St. and Charlie Hooper's at 12 W. 63rd St., with its 30 taps, are close to the shop blocks.
The Saturdays Fill In the Rest
Two Saturdays in the season serve a different purpose. Cookies, Cocoa & Crafts on November 14 runs from 11 a.m. to 2 p.m., at a time when HomeGrown at 338 W. 63rd St. is serving breakfast, brunch, and lunch, and Bella Napoli at 6229 Brookside Blvd. is running its pizzeria and Italian market. Foo's Fabulous Frozen Custard at 6235 Brookside Plaza is a few doors from the tree, and families with kids will probably stop there.
Small Business Saturday falls on November 28, two days after Thanksgiving. It's the one Saturday on the calendar in the middle of the season, and it fills the gap between the November 19 Thursday and the December 3 Thursday.
For the last shopping stop before the holidays, the final extended-hours Thursday is December 17. Cosentino's Market in Brookside at 14 W. 62nd Terrace and Mike's Wine and Spirits at 21 W. 63rd St. are both listed in the association's directory, so you can do your hosting errands in the same trip.
Brookside's holiday season is built around events like these, and so is the way we work. At Sweeney Team KC, we keep track of what's happening in the Plaza-area neighborhoods our clients call home. If you're curious what your Brookside home is worth this season, start with a free instant home valuation and we'll go over the numbers with you.
