29 days in Montana Itinerary

29 days in Montana Itinerary

Created using Inspirock Montana trip builder

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Make it your trip
Fly
1
Billings
— 3 nights
Drive
2
Red Lodge
— 1 night
Drive
3
Bozeman
— 6 nights
Drive
4
West Yellowstone
— 4 nights
Drive
5
Dillon
— 1 night
Drive
6
Helena
— 4 nights
Drive
7
Missoula
— 4 nights
Drive
8
Whitefish
— 5 nights
Fly

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Billings

— 3 nights
Billings is the largest city in the state of Montana, and is the principal city of the Billings Metropolitan Area with a population of 166,855.Billings is located in the south-eastern portion of the state and is the seat of Yellowstone County, which had a 2015 population of 157,048. Discover out-of-the-way places like The Grand Escape Room and Yellowstone Art Museum. Visiting Horseback Riding Tours and The Rimrocks will get you outdoors. Step out of Billings to go to Crow Agency and see Custer Battlefield Trading Company, which is approximately 1h 5 min away. Next up on the itinerary: examine the collection at Moss Mansion, take an in-depth tour of Yellowstone County Museum, sample the tasty concoctions at Yellowstone Valley Brewing Company, and look for gifts at Scheels.

To see ratings, traveler tips, more things to do, and tourist information, refer to the Billings trip planner.

New York City to Billings is an approximately 8-hour flight. You can also drive; or take a bus. The time zone difference when traveling from New York City to Billings is minus 2 hours. Expect slightly colder temperatures when traveling from New York City in December; daily highs in Billings reach 33°F and lows reach 17°F. Wrap up your sightseeing on the 30th (Wed) to allow time to drive to Red Lodge.

Things to do in Billings

Museums · Historic Sites · Nature · Outdoors

Side Trip

Red Lodge

— 1 night
Red Lodge is a city in and the county seat of Carbon County, Montana, United States. On the 31st (Thu), contemplate the waterfront views at Wild Bill Lake, then fly down the slopes at Red Lodge Mountain, and then stop by Montana Candy Emporium.

For other places to visit, photos, reviews, and tourist information, use the Red Lodge trip planner.

Drive from Billings to Red Lodge in 1.5 hours. In December, daytime highs in Red Lodge are 34°F, while nighttime lows are 14°F. Finish your sightseeing early on the 31st (Thu) so you can travel to Bozeman.

Things to do in Red Lodge

Parks · Shopping · Winter Sports · Nature

Bozeman

— 6 nights
Bozeman is a city in and the county seat of Gallatin County, Montana, United States, in the southwestern part of the state. Step out of the city life by going to Lewis & Clark Caverns State Park and Fishing Charters & Tours. Eschew the tourist crowds and head to Bridger Bowl and Gallatin Canyon. Venture out of the city with trips to Virginia City (J.Spencer Watkins Memorial Museum & Virginia City National Historic Landmark), Madison Buffalo Jump State Park (in Three Forks) and Horseback Riding Tours (in Big Sky). The adventure continues: admire the sheer force of Palisade Falls, brush up on your knowledge of spirits at Bozeman Spirits Distillery, test your team's savvy at Escape Room Montana, and take an in-depth tour of American Computer & Robotics Museum.

To see reviews and other tourist information, go to the Bozeman trip itinerary maker tool.

Traveling by car from Red Lodge to Bozeman takes 2.5 hours. Traveling from Red Lodge in December, expect slightly colder with lows of 8°F in Bozeman. Finish up your sightseeing early on the 6th (Wed) so you can go by car to West Yellowstone.

Things to do in Bozeman

Nature · Parks · Outdoors · Winter Sports

Side Trips

West Yellowstone

— 4 nights
The town of West Yellowstone has served as a gateway to Yellowstone National Park since the early 1900s.
Discover out-of-the-way places like Grizzly Outfitters Ski & Backcountry Sports and Back Country Adventures. Take a break from the city and head to Two Top and Horseback Riding Tours. Take a break from West Yellowstone with a short trip to Ousel Falls Trail in Big Sky, about 1h 5 min away. And it doesn't end there: get outside with Outdoor Activities, see what you can catch with a fishing tour, find something for the whole family at Yellowstone Big Gun Fun, and explore the activities along Hebgen Lake.

To see reviews, traveler tips, photos, and more tourist information, read West Yellowstone trip planner.

You can drive from Bozeman to West Yellowstone in 2 hours. Another option is to do a combination of bus and shuttle. Plan for slightly colder temperatures traveling from Bozeman in January, with highs in West Yellowstone at 21°F and lows at -2°F. Wrap up your sightseeing on the 10th (Sun) to allow time to travel to Dillon.

Things to do in West Yellowstone

Outdoors · Parks · Tours · Nature

Side Trip

Dillon

— 1 night
Dillon is a city in and the county seat of Beaverhead County, Montana, United States. Kick off your visit on the 11th (Mon): contemplate the waterfront views at Beaverhead River, then mingle with the ghosts of the past at Bannack State Park, and then stop by The Bookstore.

Plan trip to Dillon with our itinerary maker to find out where to go and what to do.

Traveling by car from West Yellowstone to Dillon takes 3 hours. Expect a bit warmer temperatures when traveling from West Yellowstone in January; daily highs in Dillon reach 34°F and lows reach 15°F. Cap off your sightseeing on the 11th (Mon) early enough to travel to Helena.

Things to do in Dillon

Nature · Parks · Historic Sites · Shopping

Helena

— 4 nights
Helena is the capital city of the U.S. state of Montana and the county seat of Lewis and Clark County. Get in touch with nature at Mount Helena and Giant Springs State Park. You'll explore the less-touristy side of things at Cathedral of St. Helena and C.M. Russell Museum. Next up on the itinerary: catch some excitement at Great Northern Carousel, steep yourself in history at Original Governor's Mansion, get a sense of history and politics at Montana State Capitol, and get engrossed in the history at Montana Historical Society Museum.

To find other places to visit, ratings, traveler tips, and more tourist information, use the Helena online journey maker.

Drive from Dillon to Helena in 2.5 hours. In January, daily temperatures in Helena can reach 32°F, while at night they dip to 13°F. Finish up your sightseeing early on the 15th (Fri) so you can go by car to Missoula.

Things to do in Helena

Nature · Parks · Historic Sites · Wildlife

Side Trip

Missoula

— 4 nights
Missoula is a city in the U.S. state of Montana and is the county seat of Missoula County. Visiting Rocky Mountain Elk Foundation and Lee Metcalf National Wildlife Refuge will get you outdoors. You'll explore the less-touristy side of things at Daly Mansion Preservation Trust and US-12. Explore the numerous day-trip ideas around Missoula: Philipsburg (Gem Mountain Sapphire Mine, Philipsburg Brewing Company, &more). There's much more to do: find something for the whole family at A Carousel for Missoula, deepen your understanding at University of Montana, examine the collection at Museum of Mountain Flying, and indulge your thirst for a good beer at Big Sky Brewing.

To find traveler tips, reviews, photos, and tourist information, you can read our Missoula trip builder.

You can drive from Helena to Missoula in 2 hours. Another option is to take a bus. In January in Missoula, expect temperatures between 31°F during the day and 17°F at night. Finish your sightseeing early on the 19th (Tue) so you can drive to Whitefish.

Things to do in Missoula

Wildlife · Parks · Breweries & Distilleries · Historic Sites

Side Trips

Whitefish

— 5 nights
Whitefish is a city in Flathead County, Montana, United States. Step out of the city life by going to Whitefish Lake Golf Club and Highline Trail. Deepen your sense of the past at sights like Conrad Mansion and Saint Matthew's Church. Step out of Whitefish to go to Lakeside and see Blacktail Mountain Ski Area, which is approximately 40 minutes away. There's lots more to do: test your team's savvy at Hidden Key Escape Games & Rage Room, don't miss a visit to Whitefish Pottery, brush up on your knowledge of spirits at Glacier Distilling Company, and kick back and relax at City Beach.

For ratings, photos, other places to visit, and tourist information, read our Whitefish holiday planner.

You can drive from Missoula to Whitefish in 3 hours. Other options are to take a bus; or do a combination of bus and train. January in Whitefish sees daily highs of 31°F and lows of 16°F at night. You will have some time to spend on the 24th (Sun) before leaving for home.

Things to do in Whitefish

Parks · Outdoors · Trails · Breweries & Distilleries

Side Trips

Montana travel guide

4.7
River Rafting & Tubing · Bodies of Water · Nature & Parks
The Crown of the Continent
With a population of only one million, Montana remains an untouched natural paradise of snowcapped peaks, expansive forests, and alpine lakes, dotted with Old West ghost towns, Indian reservations, and progressive urban communities. Appreciate the state's unique charm and beauty with a trip to Glacier National Park, where you can come face-to-face with Montana wildlife among its high peaks. Head to the state's largest cities, Billings and Missoula, for an array of historical attractions and cultural sightseeing.