Billings Blog

Winston’s Naughty & Nice List

Winston’s Naughty & Nice List

November 24, 2025

Arts, Culture & Events
Family Fun
Itineraries
Local Flavor
Outdoor Adventure

Fall in Billings, MT: Seasonal Adventures You Can’t Miss

From pumpkin patches and farmers markets to festivals, Billings is bursting with things to explore.

Family Fun
Outdoor Adventure

If You’re a Rock Climber, Here’s Your Day in Billings, Montana

Rock climbing in Billings is as iconic as the formations you’re climbing.

Itineraries
Local Flavor

Best Places to Eat and Drink in Billings, MT

Billings offers unforgettable flavors at every turn.

Winston's Blog

Winston’s Guide to the Perfect Girls’ Weekend in Billings

I can help you plan the perfect girls’ getaway in Billings

Itineraries
Outdoor Adventure

Your Step-by-Step Guide to 50 Miles of Awesome Experiences

Lace up your boots, pump up those tires and get ready for a tour through epic Montana landscapes.

Family Fun
Outdoor Adventure

8 Big Billings Experiences

Experiencing authentic Montana culture and adventuring through the American West.

Family Fun
Outdoor Adventure

Water Adventures in Billings: Where the Rivers Run Wild and the Good Times Flow

In Billings, water is more than a feature on the map. It’s a big Montana experience.

Family Fun
Itineraries
Local Flavor
Outdoor Adventure

A Family Vacation In the Big City Under Big Skies!

This four-day itinerary brings your family into the heart of Montana’s biggest city.

Family Fun
Itineraries
Outdoor Adventure
Roadtrips

The Beartooth Scenic Highway

The Beartooth Highway, is one of the most scenic drives in the United States.

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