What does the plaza next to Wrigley Field do on a Tuesday night in October with no game on? On Tuesday, Oct. 13, from 6 to 8 p.m., Gallagher Way is running a free game night with Stewpendous Productions. That night is listed as one of several "NEW" series on a fall calendar with something on almost every day of the week.
That calendar says something about Wrigleyville in 2026. The blocks around the ballpark keep a second schedule that has nothing to do with first pitch. It covers the free weekday events in October, the winter market in November and December, and the Clark Street restaurants that scheduled their openings for months when the stadium was dark. Even the biggest land-use decision near the ballpark this fall came down to people who live nearby.
Two Weeks Of Free Plaza Before The Market Goes Up
Gallagher Way's calendar has a clear end date for this phase. From Monday, Oct. 26 through Saturday, Oct. 31, the park is closed to the general public while crews build out the Christkindlmarket. Until then, these are the listings:
- Weekday mornings, 7 to 8 a.m.: Free fitness classes. The calendar shows all-levels yoga, HIIT on Wednesdays, and dance cardio and sculpt on Fridays.
- Wednesday, Oct. 14, 6 to 10 p.m.: Toyota Movie Nights screens The Nightmare Before Christmas. Free.
- Fridays, Oct. 16 and Oct. 23, 5 to 9 p.m.: Friday Night Happy Hour.
- Saturday, Oct. 17, 11 a.m. to 7 p.m.: The Beer Garden at Gallagher Way, also labeled new this year.
- Sunday, Oct. 18, 11:30 a.m. to 6 p.m.: Pumpkins & Pigskins, with football games shown outdoors.
- Tuesday, Oct. 20, 6 to 8 p.m.: Music bingo, the second Stewpendous game night. Free.
- Wednesday, Oct. 21, 6 to 10 p.m.: Hocus Pocus on the outdoor screen. Free.
- Thursday, Oct. 22, 4 to 9:30 p.m.: Lucky Dorr's annual Pups Halloween, a dog costume event. Free.
- Saturday, Oct. 24, 1 to 5 p.m.: Pumpkin Party at Gallagher Way. Free.
Look at the timing. Most of these events land on weeknights and weekday mornings, when the crowds that fill this plaza in summer have gone home. A dog costume contest at 4 p.m. on a Thursday and a 7 a.m. HIIT class make use of those quieter weekday hours.
The Winter Handoff On Nov. 20
When the plaza reopens, the programming changes. Christkindlmarket Wrigleyville runs at Gallagher Way, 3635 N. Clark St., from Nov. 20 through Dec. 31, 2026. The market's official page lists these regular hours:
| Days | Hours |
|---|---|
| Monday to Thursday | 3 to 9 p.m. |
| Friday and Saturday | 11 a.m. to 9 p.m. |
| Sunday | 11 a.m. to 7 p.m. |
The holiday exceptions are where people get caught out. On Thanksgiving, Nov. 26, the market is open 11 a.m. to 4 p.m. Hours stretch to 11 a.m. to 9 p.m. from Dec. 21 to 23 and again from Dec. 28 to 30. Christmas Eve and New Year's Eve both close at 4 p.m., and the market is closed on Christmas Day.
Winterland at Gallagher Way is listed for the same window, starting Friday, Nov. 20 and running through Dec. 31. As of today, its official event page says more information is coming. The Winterland FAQ online still shows last season's details, so any rink prices you see there are 2025 numbers. The calendar also doesn't say whether the plaza is open between the end of the build-out on Oct. 31 and opening day on Nov. 20.
Clark Street Opened For The Off-Season Too
The plaza isn't the only part of Wrigleyville planning for the months without baseball. Some of this year's biggest Clark Street arrivals were scheduled for late winter, well ahead of the home opener.
Hattie B's Hot Chicken was set to open on Thursday, Feb. 26 at 3649 N. Clark St., right at Gallagher Way. FOX 32 Chicago reported that the restaurant would be the Nashville company's first Illinois location, its first in the Midwest and its 16th restaurant overall, serving hot chicken, Southern sides and cocktails. The same report says two more Chicago locations are planned by early 2027, one in River North and one in Wicker Park.
Kincade's took the former Lost Never Found and Casey Moran's space at 3660 N. Clark St. Block Club Chicago reported in March that the bar planned a soft opening in early March and a full launch before the Cubs' home opener. The move came 40 years after Kincade's first opened in Lincoln Park. The Kincade's website now lists Wrigleyville as one of its two Chicago locations, though neither source gives the exact day it opened.
A few blocks south, Level Sporting Club, a bar built around women's sports, opened at 3343 N. Clark St. It was still waiting on its city liquor license in April. The Infatuation's review described it as just opened on June 8. A bar centered on women's sports pulls from a schedule that keeps going after the Cubs' season ends.
Next on the list is Portillo's. Block Club Chicago reported in July that the chain plans its first Wrigleyville restaurant at 3519 N. Clark St., with a walk-up window and a small indoor dining area. The opening is expected in 2027, so it won't be part of this winter.
Two Spaces That Changed Character
Not every 2026 change added something. Block Club Chicago reported in late May that Lucky Strike permanently closed its venue at 1027 W. Addison St., across from the ballpark, leaving a space of roughly 30,000 square feet empty. No replacement has been announced as of this writing.
The same report covered a smaller change inside the ballpark complex. DraftKings ended in-person sportsbook betting at Wrigley Field starting May 31, and the space stayed open as a sports bar.
For a quiet October, it's useful to know which spaces near the stadium are open and which aren't. Right now, the vacant Lucky Strike space on Addison has no announced future.
Neighbors Weighed In On The Parking Lot
The clearest sign that the off-season belongs to the neighborhood came on Oct. 6. Ald. Bennett Lawson of the 44th Ward rejected the Cubs' proposal to expand the Camry Lot north of Wrigley Field beyond the 800 spaces it already has permits for. The team had proposed growing the lot from its current 688 spaces to as many as 947 by adding the former House of the Good Shepherd property, which it bought from Catholic Charities. Block Club Chicago reported the decision, and Lawson cited strong opposition from neighbors along with concerns about traffic and pedestrian safety.
The ward's survey numbers explain the outcome. Of 490 respondents who identified as 44th Ward residents, 438, which Block Club Chicago reported as 89.5%, opposed the expansion. Twenty-nine, or 6%, supported it. Among 233 respondents living within four blocks of the lot in the 44th and 46th wards, 84.1% opposed it and 5% supported it. One survey comment quoted by Block Club Chicago pictured a different use for the land:
"The former House of the Good Shepherd moving creates a great opportunity to develop valuable land into a transit-oriented, mixed-use building to better fit with the walkable and transit-rich neighborhood of Wrigleyville."
The decision doesn't settle the site's future. Per the same report, the Cubs still own the former House of the Good Shepherd property and can still build out to the 800 permitted spaces. A planned-development amendment that addresses compliance issues and the site plan is still in process, along with work on traffic management. That amendment is the next public step to watch for anyone following what happens to the land west of the ballpark.
The Calendar From Here
The order of events is simple. Gallagher Way has two more weeks of free movies, game nights, morning classes and the Oct. 24 Pumpkin Party. The plaza closes Oct. 26 to 31 for the build-out. Christkindlmarket and Winterland open together on Nov. 20 and run through New Year's Eve, with Winterland's 2026 details still to come. Along Clark Street, the 2026 arrivals at Gallagher Way, 3660 N. Clark and 3343 N. Clark don't depend on a game schedule. If you're planning a weekend that crosses the neighborhood, our guide to Southport and Broadway's biggest weekend covers Lakeview's other two commercial streets, and the Lakeview/Wrigley neighborhood page has the wider picture.
At The Kelly Ladewig Group, we keep track of the Wrigleyville calendar after the last out, from Pumpkin Party to the Camry Lot amendment. If you're curious how a quieter, year-round Clark Street affects the homes around the ballpark, start with our notes on buying near Wrigley Field. When you're ready to see the blocks for yourself, let's go house hunting.
