Overview
Plentywood is a city in Eastern Montana, in Sheridan County. The area's wild history includes the famous Outlaw Trail, then becoming a communist community during the Great Depression.
6 places to eat · 4 bars & cafés · 1 places to stay
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Plan your trip
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- XWA Williston Basin International Airport, Williston — 51 mi away. Directions
- OLF L M Clayton Airport, Wolf Point — 66 mi away. Directions
Plentywood is remote so you will need a car to get there.
Full “Get in” guide ↓Budget & where to stay
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Food for you
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Understand
Sheridan County is a rural community whose commerce centers around the family farm and ranch. They have substantial oil exploration and development, a brisk Canadian trade, abundant wildlife, and a country personality where friends are friends indeed. There is something unique and special in small-town living. Everyone in Sheridan County can assure you of that!
History
The county was organized April 1, 1913. Plentywood had incorporated in 1912 and was chosen as the County Seat.
The Outlaw Trail started at the Outlaw Caves in southern Saskatchewan, Canada, and wound its way south through Sheridan County and as far south as Wyoming and beyond. The trail was in heavy use during Sheridan County's early days. Romantic stories abound concerning these famous outlaws who stole cattle and horses and occasionally robbed a bank or two, escaping and evading the law.
The Communist era in the 1930s was another colorful time. The Communists moved in and labored long and hard to convert the citizens to their political ways. They infiltrated the county government, had their own newspaper, and provide today's interesting tales of their struggles during their rise and fall.
The oil boom of the 1970s and early 80s also added a robust flavor to life. As the population in the county more than doubled, the "live fast - work hard" lifestyle became commonplace as poker chips from local saloons were treated as legal tender almost anywhere in the county.
Get in
Plentywood is remote so you will need a car to get there.
It is at the intersection of State Highway 16 (MT-16) and State Highway 5 (MT-5).
- From Canada, take Saskatchewan Highway 6 south.
- From North Dakota, take North Dakota Highway 5 west.
The nearest commercial airports are in Williston, North Dakota or Regina, Saskatchewan. Both have car rental companies.
Get around
The town is fairly spread out so a car or bike is needed. There is a central section of town, with some shops and eating places, that can easily be walked.
When adventuring outside of town, be sure you plan for fuel and download maps. Wide open country is great to explore, just don't expect to always have service and amenities.
Do
You can go bowling, watch a movie, play in the park, and fish at the dam.
Eat
Drink
Sleep
Go next
- Brush Lake (30 miles east) is a mile long lake great for any water activity.
- Medicine Lake Wildlife Refuge (22 miles south) has hundreds of species of migratory birds.
Nearby
Scobey
City / town · 1 listings · 39 mi away
Crosby
City / town · 8 listings · 58 mi away
Williston
City / town · 31 listings · 60 mi away
Wolf Point
City / town · 10 listings · 69 mi away
Cartwright
City / town · 3 listings · 70 mi away
Sidney
City / town · 13 listings · 76 mi away
Alexander
City / town · 5 listings · 77 mi away
Tioga
City / town · 4 listings · 79 mi away
My experience
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