If you live here, you already know September is not a slow shoulder-season month. It is the busiest stretch of the year that most people outside the county still think of as "after summer." Two weekends back-to-back pull in tens of thousands of visitors, fill every parking lot on Mt. Rushmore Road, and briefly turn our town into a staging area for events that get broadcast on public television. Then, almost overnight, the crowds thin and the lodges close for the season.
The trick to enjoying it as a resident is knowing which weekend to lean into and which one to plan around. They are not interchangeable.
The two weekends that decide September
| Weekend | Event | Scale | Where the pressure lands |
|---|---|---|---|
| Sept 17–20 | 28th Annual Fall Mickelson Trail Trek | Hundreds of riders across three days | Downtown Custer lodging, dinner tables, Mt. Rushmore Brewing Company |
| Sept 25–27 | 61st Annual Buffalo Roundup + Arts Festival | 20,000+ spectators on Friday morning alone | Wildlife Loop Road, State Game Lodge grounds, breakfast spots |
The Fall Mickelson Trail Trek follows the George S. Mickelson Trail, winding 109 miles through the Black Hills, and this year's ride is based out of Custer on Friday and Saturday, then wraps up in Deadwood on Sunday. One week later, the 61st Annual Custer State Park Buffalo Roundup runs on Friday, September 25, 2026, alongside the Buffalo Roundup Arts Festival, showcasing over 150 vendors with fine art, crafts, and food.
Two very different crowds, two very different rhythms, two weekends where knowing what happens on the ground matters more than knowing the marquee facts.
Trail Trek weekend: the quiet one, if you plan it right
The Trek is the sneakier of the two events for residents. It does not swamp the town the way the Roundup morning does. What it does is fill every restaurant table in the evenings, because riders use a Mickelson Trail Voucher for dinner in Custer or Hill City and most of them cash it in downtown.
Check-in sets the tone. On Thursday, September 17, from 2:00 to 8:00 PM, riders pick up their packets at Mount Rushmore Brewing Company in Custer, and the back of that building becomes an informal social hub for the weekend. If you were planning a low-key Thursday beer at Mt. Rushmore Brewing, that is the night to pick a different bar. The Gold Pan Saloon down the street, with its cowhide barstools and Old West bones, is a reasonable pivot.
Friday morning the riders ship out toward Edgemont. On Saturday, participants ride from Custer to Rochford, then get shuttled back to Custer, which means Saturday dinner is when downtown gets pressed hardest. If you want a table at Skogen Kitchen without a wait, book Wednesday of that week. If you want the reservation experience without the reservation, Baker's Bakery & Cafe stays true to its role as a longtime Custer institution and takes walk-ins.
For riders you know, or friends coming in to ride, there is a small local detail worth passing along: late check-in moves to the Custer Chamber of Commerce at 615 Washington St. Nobody who has not done the ride knows that, and it saves a phone call.
Roundup morning, without the rookie mistakes
The Roundup is the weekend the whole town feels. If you have lived here for more than a season, most of this is old news, but the logistics change slightly each year and it is worth checking before Friday.
Here is the shape of the morning as the park is running it in 2026:
- Parking lots open at 6:15 a.m. The Buffalo Roundup begins at 9:30 a.m. MT on September 25, with parking lots opening at 6:15 a.m. Locals treating this like a 9:00 start end up parked in overflow.
- Pick your viewing area before you leave the house. North Parking heads south from the Game Lodge area on Wildlife Loop Road; South Parking heads east on Wildlife Loop Road near Blue Bell campground. You cannot switch mid-drive without backtracking.
- Breakfast is on-site, for a fee. Breakfast is available at 6:15 a.m. in both viewing areas, lunch is served at the corrals once the buffalo are rounded up, and there is a fee for both meals. Pancakes and sausage, hot beverage. Not the moment to try to fit in a Feel Good Cafe stop on the way out of town.
- Leave the dog. The park encourages you to leave your pets at home. Every year somebody tests this and regrets it.
- Stay put after the drive. Testing, branding, and sorting of the buffalo begins at 1 p.m. and lasts until approximately 3 p.m. This is the part most one-time visitors skip and most residents like the best.
The crowd number is worth an internal check on your patience level. This is a high-profile public event, with as many as 20,000+ spectators present on Roundup morning. If that number lands wrong, treat Friday as a stay-in-town day and go to the Arts Festival on Saturday when the same 150 vendors are set up with a fraction of the crowd.
Where locals eat when the town is full
Custer's dining scene has quietly outgrown its "gateway town" reputation in the past few years, and September is when the depth of it becomes obvious. Different meals belong at different addresses.
Breakfast, early: Baker's Bakery & Cafe is the default for a reason. Baker's Bakery & Cafe is a Custer institution, offering freshly baked goods, hearty breakfasts and homestyle lunches. If you want the newer angle, Hjem A.M. serves Scandinavian-inspired breakfast and brunch fare including smorrebrod, a Danish open-faced sandwich, and Swedish pancakes in a snug, minimal space. On Roundup Friday, both fill up early. The Feel Good Cafe near the Bavarian Inn is the pressure-release option most out-of-town visitors do not know about.
A pack-it-and-go lunch: Wild Spruce Market combines a cafe and market where you can grab a gourmet sandwich and browse locally sourced goods. It is the smartest solution for anyone who booked a north viewing area and wants to eat something other than corral lunch at 12:30.
Dinner, the serious version: Skogen Kitchen is the room to book in advance. The chef-driven restaurant serves unique breakfast and dinner items in downtown Custer, and it is the one Travel South Dakota keeps pointing at when it wants to describe South Dakota's food scene rather than its buffet culture. The Custer Wolf is the other option, an elevated dining experience with a focus on wild game and local ingredients. Between the two, Skogen leans more inventive and The Custer Wolf leans more comfort-forward.
Dinner, the low-effort version: Buglin' Bull, Mt. Rushmore Brewing Company, and the Gold Pan Saloon do what they do. Steak, burgers, pub food, and beer, in that order. On Trail Trek weekend, Mt. Rushmore Brewing is effectively the riders' clubhouse; that is a feature or a bug depending on your mood.
Inside the park, while you still can: The dining rooms at Custer State Park are open seasonally from the beginning of May through mid-October. Sylvan Lake Lodge and Blue Bell Lodge are both open through the Roundup weekend and then close for the winter within a few weeks. September is the last realistic chance to drive out for the double-peaked wooden ceiling at Sylvan Lake or the French Creek patio at Blue Bell without waiting until Memorial Day.
The Custer that comes back in October
By the first weekend of October, the town exhales. The Trek riders have gone home. The Roundup infrastructure is packed up. The remaining park work happens quietly. Crews will work the remainder of the herd in October, but that is behind-the-scenes and not a public event.
There is one more date worth putting in your phone: the annual Buffalo Auction, held the third Saturday in November, which is where the population-management piece of the Roundup actually resolves. It is a smaller, working event and one of the more genuinely local things on the fall calendar.
If you moved here in the last year or two, this is the month that will teach you the most about what living in Custer actually feels like. The rhythm is not summer, and it is not winter. It is the shoulder that carries both.
Whether you are settling into your first fall in Custer or thinking about what a next chapter in the Black Hills could look like, David Kahler and our team live and work in these communities year-round. We'll handle your home — get a free home valuation and let's talk about what's next.
