When does Deadwood go quiet this winter? Going by the calendars posted so far, on Tuesday nights, and almost never on a weekend. Every weekend from November 7 to December 19 has something dated on it.
The rink at Outlaw Square reopened on October 23 and runs six days a week until the end of April 2027. Two new venues opened in September, one inside the Landmark Hotel & Casino and one at Tin Lizzie Gaming Resort. And a set of holiday events from the Chamber, Deadwood History and downtown businesses covers the Saturdays between early November and the week before Christmas. Taken together, the rink and the new venues cover the weeknights and the calendar covers the weekends.
The Rink Sets the Weekly Rhythm
Outlaw Square's winter season opened October 23, 2026, and runs through the end of April 2027. Sessions switch between open skating and ice bumper cars during the day, so when you go matters as much as which day you pick. The surface is Glice, a synthetic material made for skating, and Outlaw Square says plainly that it is not real ice. Bring your own skates or rent a pair there. Here is the posted weekly schedule:
| Day | Skating | Ice Bumper Cars |
|---|---|---|
| Monday | 6 to 8 p.m. | 3 to 6 p.m. |
| Tuesday | Closed | Closed |
| Wednesday and Thursday | 3 to 5 p.m. and 7 to 8 p.m. | 5 to 7 p.m. |
| Friday | 5 to 7 p.m. | 3 to 5 p.m. and 7 to 9 p.m. |
| Saturday | Noon to 2 p.m. and 5 to 7 p.m. | 2 to 5 p.m. and 7 to 9 p.m. |
| Sunday | Noon to 2 p.m. and 4 to 6 p.m. | 2 to 4 p.m. and 6 to 8 p.m. |
Outlaw Square says the schedule can change and posts updates on its website and Facebook page, so check before you bring a carload of kids. The bumper cars have rules that every family will want to know before the line:
- To drive a car alone, a rider must be at least 6 years old and at least 42 inches tall.
- To carry a passenger, the driver must be at least 16 and the passenger must be 3 to 5 years old, with no exceptions.
- The combined weight of everyone in a car can't exceed 300 pounds.
So a family with a 4-year-old can only ride bumper cars together if a teenager or adult is driving. A 7-year-old who is tall enough can drive alone.
Two New Rooms Fill In Around the Rink
The rink is closed only on Tuesday. The two venues that opened this fall cover much of the rest of the week, which is why the weeknights don't feel empty this year.
Ian Munsick's Cowboy Bar & Western Grill opened September 18 inside the Landmark Hotel & Casino. The Wyoming-native country singer partnered with the Landmark on the venue. According to the Landmark's page for the venue, it's open Wednesday through Sunday for breakfast, lunch and dinner, with country and western decor and two stages, one indoors and one outdoors. It takes up more than 2,600 square feet of a building the Landmark calls Deadwood's largest historic structure. The building was built between 1894 and 1920 and covers about 35,000 square feet. The Landmark's page also carries a quote from Munsick about where the idea started:
"The brainchild of my wife, Caroline, you won't find a better place to have a beer or three than our new oasis of the West."
Tin Lizzie Gaming Resort opened Bookie's in the former Paddy O'Neill's Irish Pub space. It's a sportsbook, restaurant and whiskey bar together. KOTA reported that the menu includes charcuterie boards, tacos and specialty pasta dishes, and that the room has private whiskey lockers, lounge seating, several televisions and dedicated viewing areas for sports fans. Its grand opening weekend, October 9 and 10, has already passed, so Bookie's is simply open now.
Put those hours next to the rink schedule and a Wednesday or Thursday evening comes together. Skate from 7 to 8 p.m. on Outlaw Square, then have dinner at the Munsick venue, which is closed Monday and Tuesday. Tuesday is the one night when neither the rink nor the Cowboy Bar is open.
The Weekends, In Order
The season's dated events start on a Thursday at noon. These dates come from the listings on Deadwood's official events calendar, which notes that dates can change:
- Thursday, November 5. Preservation Thursday at the Homestake Adams Research and Cultural Center, free, at noon. Deadwood preservation officer Kevin Kuchenbecker and Deadwood Gaming Association executive director George Milos will talk about the town's historic preservation work and the effect of legalized gaming.
- Saturday, November 7. Wine, Cheese & Chocolate Stroll.
- Saturday, November 14. Deadwood's 150th Motorcycle Giveaway Party at Saloon No. 10.
- Weekend of November 20 to 22. Holiday Ho-Ho Horseshoes starts Friday, November 20, and runs through December 30. It is the only event on the calendar that weekend.
- Friday and Saturday, November 27 and 28. The first Candlelight Christmas Tours at the Historic Adams House, plus Dueling Pianos at Cadillac Jack's on the 27th.
- Friday and Saturday, December 4 and 5. The busiest weekend, covered below.
- Friday and Saturday, December 11 and 12. The second annual Kringle Crawl and the third Adams House weekend.
- Friday and Saturday, December 18 and 19. The last Candlelight Christmas Tours of the season.
The Adams House tours run on four of those weekends, so they're the easiest to fit in around everything else. Deadwood History's listing says the decorated Queen Anne-style house at 22 Van Buren Street will be lit by candlelight while guides talk about Christmas traditions and the families who lived there. Tours start every half hour from 11 a.m. to 4 p.m. The detailed listing gives prices of $8 for members, $12 for nonmembers, $5 for ages 6 to 12, and free for kids 5 and under. Members should call for tickets. The summary line at the top of that page shows a different price range, so call 605-722-4800 or check DeadwoodHistory.com before you go.
December 4 and 5 Is Where Everything Stacks
Most of the winter's free events land in one 24-hour stretch.
Community Christmas at Outlaw Square starts Friday, December 4. The Deadwood Chamber's annual recognition awards are at 5:30 p.m. and the tree lighting is at 6, with Santa arriving afterward and free skating on the rink. The Adams House runs candlelight tours on both days.
On Saturday, December 5, the Days of '76 Museum holds its Holiday Open House from 10 a.m. to 4 p.m. Deadwood History lists it as free, with children's activities, face painting, holiday gifts, refreshments, free museum admission, and photos with Santa and Mrs. Claus from 11 a.m. to 2 p.m. Hairball plays Deadwood Mountain Grand that night.
So a family can see Santa on Friday evening at the tree lighting and again on Saturday at the museum, and skate free on Friday, without buying a ticket for any of it.
The Horseshoe in Your Pocket Lasts Longest
The longest-running event this season costs a little money and also supports downtown businesses. From November 20 through December 30, five businesses sell numbered horseshoe ornaments: the Landmark Hotel & Casino, Silverado, Madam Peacocks Beer & Bling, Saloon No. 10 and Antiques 1876. Each horseshoe comes with a limited-edition holiday postcard by local artist Cari Thrall.
Participating businesses will post winning numbers in their stores. If your horseshoe number matches, you collect the prize on the spot. Every prize is worth at least $50, and up to 100 horseshoes will win. The list of businesses with prizes hasn't been released yet, per the Ho-Ho Horseshoes listing. Once it is, each trip downtown for skating, a tour or dinner is also a chance to check your number.
The Kringle Crawl on December 11 and 12 is the event for adults. The Chamber's listing describes it as a fundraiser for the Deadwood Chamber of Commerce & Visitors Bureau. It's 21 and over, capped at 400 people, and tickets are nonrefundable. The Chamber still lists the full schedule as coming soon. The Local Black Hills event listing currently shows Friday registration at the Eagle Bar from 4 to 7 p.m. and a cocktail crawl from 5 to 8 p.m. Saturday has registration from noon to 3 p.m., shopping discounts, a pub crawl from 3 to 7 p.m. and an awards after-party at 7:30. On the event's Eventbrite ticket page, tickets are listed at $44.43. Treat that schedule as tentative until the Chamber posts its own.
Last year's first Kringle Crawl, as the Rapid City Post described it, had a Friday cocktail crawl with themed drink samples at 15 to 16 stops. Saturday brought a "Santa Shop Around" with exclusive discounts at downtown stores, then a pub crawl and an after-party with a DJ and contests. This year's tentative schedule follows a similar Friday-and-Saturday pattern. With a 400-person cap, tickets may not last until the week before.
After the Crawl, the Adams House has one more candlelight weekend on December 18 and 19, the horseshoes run through December 30, and the rink stays open until the end of April.
I've called the northern Black Hills home since 1980, and I like a December when the reason to go downtown is a tree lighting or a candlelit tour. If you're new to Deadwood and still learning where the town gathers this time of year, or you want to talk about anything else around here, Sandra Donahue would be glad to hear from you. Let's Connect.
