From Monster Mash to Christmas Stroll: Sheridan's Downtown Calendar for Late Fall

At 8 a.m. this Saturday, Main Street and Grinnell Plaza close to cars and open to kids in costume. Five weeks later, on the Friday after Thanksgiving, the same two streets close again, this time at 4 p.m. for hay wagons and marshmallow roasting. Both closures land on the same few blocks, and a number of the addresses on those blocks are new this fall or about to change.

Here is the season in order, block by block.

Saturday, Oct. 24: the street closes before breakfast

The Downtown Sheridan Association is hosting its third annual Main Street Monster Mash on Saturday, Oct. 24, Sheridan Media reported in an announcement from DSA Executive Director Zoila Perry. The morning runs on a tight schedule:

1. 8 a.m. Main Street and Grinnell Plaza close to traffic.
2. 10 a.m. The costume contest starts in front of City Hall, with local celebrity judges. There are four children's age categories, and this year adds a family costume category.
3. 10:30 a.m. Trick-or-treating starts at downtown businesses. Participating shops have small ghosts on their doors or windows.
4. Noon The streets reopen.

If you'd rather give candy than collect it, you can drop off unopened candy at the DSA Office, 121 S. Main St.

The rest of Oct. 24 is just as full, and it all happens within a short walk or drive:

The Shade Tree is a Casper clothing boutique, and The Sheridan Press reported that its Sheridan location plans a soft opening that same Saturday. That puts its first day on Main Street right in the middle of the morning's biggest crowd.

The WYO Theater's fall premiere of Anything Goes doesn't end on opening night. Matinees are at 2 p.m. on Oct. 25 and Nov. 1, and evening shows are at 7 p.m. Oct. 29 through 31. That makes Halloween night itself a curtain night downtown.

What's new on the blocks that close

Grinnell Plaza is in both street closures, and it has a new tenant this fall. The GOAT Creamery & Fizz Co. moved into 24 E. Grinnell Plaza, the former Platte Hemp Company space. The Sheridan Press reported that the shop was aiming for a Sept. 1 opening while renovations and equipment installation were still underway. The shop's own website now says "Open Now!" with these hours:

• Monday through Thursday, noon to 8 p.m.
• Friday and Saturday, 11 a.m. to 9 p.m.
• Closed Sunday

The Sheridan County Chamber of Commerce lists The GOAT as a locally owned dessert shop with ice cream, gelato, dirty sodas and other treats. The Chamber Ambassadors scheduled its ribbon cutting for Oct. 20. Because Monster Mash runs from 8 a.m. to noon and the shop opens at 11 a.m. on Saturdays, the last hour of trick-or-treating overlaps with its first hour open.

A block off Main, another opening is planned to land right around the holiday. Misty Moon Yoga & Wellness is getting a studio ready at 155 W. Brundage St., with hot yoga, strength, balance and HIIT classes. The Sheridan Press reported that the owners hope to open to the public by Thanksgiving. Thanksgiving falls on Nov. 26 this year, the day before the Christmas Stroll. If the studio opens on schedule, its first days will overlap with downtown's busiest day of the year.

What's changing hands, and what's waiting on stone

Two of downtown's best-known dining rooms are for sale. Christer and Gina Johansson own The Warehouse Gastropub, which they opened in 2022, and Le Rêve Restaurant & Raw Bar, which followed two years later. The Sheridan Press reported that the couple is looking for new owners for both and will keep running the restaurants until a buyer takes over.

The building next to Le Rêve on East Alger Street is moving more slowly. The Johanssons are turning it into a 15-room boutique hotel. They have said a later renovation could add two more floors and another 30 rooms. According to a Sheridan Press report from Oct. 1, the exterior masonry was supposed to start in October 2025 but didn't begin until April because materials shipped late. Poorly fabricated pieces for the complicated stone front caused more delays. Christer Johansson told the paper that each replacement piece has taken six to eight weeks, and the pieces have to go up in sequence.

The landscaping has moved from this fall to next spring. The interior design isn't finished, and the hotel doesn't have a name or an opening date yet. The Johanssons said they would consider selling the hotel project to the right buyer, and if no buyer comes along, they still plan to open it. "We're not going to rush anything," Christer Johansson told The Sheridan Press.

That means anyone walking East Alger during the Stroll will pass a stone facade that's still being assembled.

November, between the two closures

From Halloween to Thanksgiving, most of downtown's activity moves indoors to two places: the WYO Theater on North Main and The Brinton Museum outside town.

The Fifth Step on Nov. 5 opens the WYO's National Theatre Live 2026–2027 season series, which runs through May 2027. The Brinton's Jentel Presents series meets twice this fall. The first session is Thursday, Oct. 22, from 10:30 a.m. to noon, and the second is Nov. 19.

Two exhibitions at the Brinton run through the whole season:

• The Small Works Show opened with a reception on Sept. 25 and is on view through Dec. 21.
• William Gollings: Collected Treasures has been up since Aug. 14 and also closes Dec. 21.

Both exhibitions close on the same day, so the week before Christmas is your last chance to see either one.

The Stroll deadline comes before the Stroll

The 31st Annual Sheridan Christmas Stroll is on Friday, Nov. 27, from 8 a.m. to 8 p.m. Stroll buttons go on sale about four weeks before that.

Sheridan Media reported the button schedule from Jodi Hartley, marketing and communications director for the Sheridan County Chamber of Commerce:

1. Oct. 20: The winning button design was set to be unveiled at City Hall. Sheridan County students in grades 1 through 6 entered the contest, and this year's theme is "America's 250th Christmas."
2. Oct. 29 and 30: Buttons go out to participating businesses and go on sale to the public.
3. Nov. 2: Buttons are also on sale at the Chamber, 54 S. Main St.
4. Nov. 27: Button holders start checking for matching button numbers that morning.

Buttons still cost $5. They've sold out in past years, and the Chamber recommends buying one before Stroll day. You can buy one about a week after Monster Mash.

Main Street and Grinnell Plaza close again from 4 to 8 p.m. on Stroll day for hay wagon rides, marshmallow roasting, and free food and drinks. Santa and Mrs. Claus will be at the WYO Theater for photos with kids from 11 a.m. to 1 p.m. and again from 4:30 to 7:30 p.m. For questions, call the Chamber at (307) 672-2485 or check the Sheridan County Chamber of Commerce website.

After the Stroll, the WYO Theater closes out the year with its 4th Annual NYE Gala on Thursday, Dec. 31, which benefits the Dog & Cat Shelter.

If you're headed into town for the Stroll from a place outside Sheridan where the horses need feeding by dark, Clay Schafer and the team at Premier Horse Property know what it takes to schedule a holiday afternoon around chores. When you're ready to look at Sheridan-area acreage, barns and pasture with someone who'll ask how your horses actually live, start with View Horse Properties.