Territorial Days

The Prison Break Run begins at Grant-Kohrs Ranch at 8 a.m. and ends at the Old Prison Museum, 1106 Main Street, in Deer Lodge. The Chamber’s program describes it as a fun run, walk and road race sponsored by the Deer Lodge Athletic Association, with registration opening an hour before the start at the museum. The rest of Territorial Days follows the runners down Main Street: a parade, a car show, a street market, and a dance that runs late into the evening.

The Powell County Chamber of Commerce puts on the festival. The 36th Annual Territorial Days was held on Saturday, June 20, 2026, under the banner “Red, White & Territorial,” and the Chamber billed it as “Celebrating USA’s 250 years!” Events ran from 9 a.m. to 6 p.m. and included the run, the Jaywalkers Jamboree, food trucks, the parade, and children’s activities. The Southwest Montana travel guide describes the festival as Deer Lodge celebrating the heritage of the area with live music, food, games, the parade, and the car show.

From the ranch to Main and Pennsylvania

In 2026 the Chamber thanked Grant-Kohrs Ranch National Historic Site “for hosting the Prison Break Run and all the participants in the run.” The City of Deer Lodge set out the barricades, and Rian King-Chaveez organized the parade. The parade’s Best of Show award went to The Corner Bar, and Cutler Brothers Theater was runner-up.

An earlier Chamber program, which is undated, gives the order of the morning. The show cars left the Old Prison Yard at 11:20 a.m. to join the parade. The parade started at 11:30 from outside Muriah’s Restaurant on the corner of Main and Pennsylvania, and gift certificates went to the three best entrants. After the parade, the Pioneer Power and Tractor Association held its Antique Tractor Show on Main Street. The start time has varied. NBC Montana reported in June 2024 that the parade would step off at noon.

Paint, engine, interior

The Show & Shine is the festival’s car show. It judges three classes: Hot Rod, for cars built before 1960; Muscle Car, for cars after 1960; and Truck. Each class has awards for Best Paint, Best Engine, Best Interior, and best in category, and there are separate awards for Best Motorcycle and Overall Best of Show. The two 2026 sources disagree on where cars registered. The Chamber’s event page names the Pioneer Federal Savings & Loan parking lot at 202 N. Main Street, while its thank-you list credits Pioneer State Bank for the use of its lot. Doug Christi and his crew judged the cars, and Ed McCarthy and his crew parked them.

The 2026 winners:

• Muscle Cars: Lauren Kostoff took Best Paint, Marty Anzik Best Engine, Frank Ahl Best Interior, and Debbie Jurich Best Muscle Car.
• Hot Rods: Rob Crisler took Best Paint, Hank Adams Best Interior, Walter Schafer Best Hot Rod, and Shane and Donna Graveley Best Engine.
• Trucks: Randy Brown took both Best Paint and Best Engine, Marc Mitchell Best Interior, and Marc Drescher Best Truck.
• Motorcycle: Tim Scrivner.
• Overall Best of Show: Shane and Donna Graveley.

The Jamboree and the street dance

The Jaywalkers Jamboree starts after the parade. Vendors line Main Street selling food and drink, jewelry, clothing, toys, and art and craft items, and the Chamber’s program promises attractions “for kids and those young at heart.” The same program lists the Country Showdown at 1 p.m. on the stage at Missouri and Main. In the evening came a free street dance with the Heather Lingle Band, from 7 to 11 p.m.

Local businesses and volunteers supplied much of the 2026 festival. Fickler Oil Company lent the trailer the band played from, and The 45 Barn provided tables and chairs. Sponsors including The Montana Bar, The Cell Block Tavern, and Mount Powell Tap Room helped pay for the car show trophies, the bounce houses, the band, and swag bags for the drivers. The Chamber also thanked the Anaconda Job Corps, listed as “Randy & Kids,” for helping “with everything all day.”

A taco bar, a pie-eating contest, a burn-out

The program has changed over the years. The Chamber called the 2017 festival the 28th Annual Territorial Days Celebration and held it over two days, June 16 and 17. On the Friday there were Show N Shine registration, a Poker Run, and music and food in the Old Prison Museum yard. Saturday added a pie-eating contest and a beer garden to the run, parade, and Jamboree.

A Lively Times listing for June 17 and 18, which gives no year, describes a longer weekend:

• Friday: Activities started at 6:30 p.m. at Jaycee Park with a taco bar, free to those registering cars for Saturday. There was also a cruise along Main Street and a free outdoor movie.
• Saturday: Besides the run, there was a radio-controlled aircraft display at the airport and a free pancake breakfast for car registrants. The afternoon brought a poker run around the Pintler Loop and a burn-out competition.

In 2024, according to NBC Montana, the festival included a Brewfest on Main Street from 1 to 5 p.m. and a 50/50 drawing. The undated Chamber program also carried the festival into Sunday with the Annual Father’s Day Golf Tournament at the Deer Park Golf Course.

The heritage the festival celebrates belongs to a valley the Southwest Montana guide says was settled by ranchers, while much of the surrounding region grew from mining. The Chamber calls Deer Lodge the second oldest town in Montana. The town has gone by LaBarge City, Spanish Fork, Cottonwood, and Deer Lodge City, and is now Deer Lodge.