itineraries to entice friends to go on adventures

Adventures with friendsExplorations
Written By Laura Kay Young

Let’s play a game! I build three trip itineraries and you vote which one we go on together. What do you think?

Dillon

view down a street flanked by historic buildings with a light yellow colored courthouse at the end

Downtown Dillon, MT 📸 by istock

Look, here’s the deal. You’ve probably heard bad things about Dillon. Possibly just as bad as the things you’ve heard about Butte. For a town in Montana, this town sure does get a lot of flak. Most only deem it worthy of a stop through for the Patagucci outlet or a gas stop half way to Missoula. However, I see Dillon for what it truly is—an adventure mecca without the crowds! While there are stellar deals at the outlet, there’s truly much more to this charming town. The historic buildings show off old west style, outdoor rec abounds, and did I mention the history?

Fall foliage beyond a rock outcropping and city buildings in the distance

Quaint and picturesque, Dillon remains a bit of a hidden gem.

Where to Stay:

  • Both hot springs resorts are nearby and offer affordable lodging with deals on local attractions.

  • The Andrus Hotel is in town and includes historic charm.

  • Angler Village Inn includes a multitude of amenities including a café and a wine lounge.

First Full Day:

  • Explore Bannack Ghost Town + walk trails through Bannack State Park

  • Lunch in town + peruse the Patagonia Outlet, The Bookstore, and other shops

  • Soak in hot springs: Elkhorn Hot Springs or Jackson Hot Springs

Day Two:

  • Ski Maverick Mountain OR explore Clarks Lookout State Park OR snowshoe a trail in the Pioneer Mountains (weather dependent).

  • I’m assuming we came in and met for dinner on a Friday night so this would be the Sunday afternoon head back home agenda item. If that’s not the case and we are able to sneak in a bit more, then I would vouch for another soaking session!

West Yellowstone

cars lined up in front of old west style buildings

Downtown West Yellowstone, MT 📸 by Yellowstone Vacations

West Yellowstone, Montana appeals to the masses for good reason. The access to the park is unparalleled and the town knows how to hostess with the mostest! Winter may be even more magical than summer. Unbelievable, I know! but true. Ok, alright. I’m obviously a bit biased. Just like Dillon, you can enjoy the old west charm but with a few more restaurants and a bit higher ticket price experiences, such as dog sledding in Big Sky and snow coach or snowmobile tours in Yellowstone.

a creek running through a field of snow

Winter in Yellowstone is mesmerizing.

Where to Stay:

  • Honestly, anywhere in town is great and affordable!

  • I’ve stayed at cute little cabins, I’ve camped, I’ve stayed at the Kelly Inn.

  • Somehow I’ve landed across the street from the Grizzly & Wolf Discovery Center every time though.

Day One:

  • Dogsledding in Big Sky + snowshoe exploration

  • Coffee and treats at Mountain Mama’s

  • Snowshoe or XC ski in Yellowstone OR on the local trails

  • Dinner and storytelling time

Day Two:

  • A half or full day snowmobiling adventure

  • If we have three days, then more snowshoeing or XC skiing!

Thermopolis

view from city street of cowboy and horse statue on one side and historic buildings on the other

Downtown Thermopolis, Wyo 📸by Travel Wyoming

Thermopolis offers almost every activity you can dream up or desire both in summer and winter; outdoor adventures, museums, foodie joints, shopping, and more. Almost = downhill skiing as the missing piece. It’s an unassuming place that appears to lack opportunity but I think the town doesn’t believe in ostentatiousness. Travel Wyoming created an outline of the top 12 adventures beautifully so all we have to do is decide the order in which we want to experience each spot.

geothermal altered rocks beneath green trees and red hillsides

Hot springs 📸by istock

Where to Stay:

  • Hot Springs Hotel and Spa in East Thermopolis is close to the state park and bath house on the Bighorn River.

  • Best Western Plus Plaza Hotel is across the street from the Hot Springs Hotel but is slightly more modern in appearance.

  • Roundtop Mountain Vista - Cabins and Motel has ambiance. Ok, I selected this one for the view and an interesting experience. The options in town trend toward houses listed on VRBO.

Day One:

  • Dinopark Tycoon! errr I mean Wyoming Dinosaur Center + shopping in town, especially a visit to Merlin’s Hide Out (although it’s supposed to close in the new year so maybe not?)

  • Pack a lunch and head over to the trails in Hot Springs State Park for a walk about and a picnic

  • Soak in the State Bath House for free OR Hellie’s Tepee Pools for a small fee

  • Dinner on the town

Day Two:

  • Hike up Roundtop Mountain

  • Visit Legend Rock Petroglyph (if willing to drive 29 mi northwest of Thermopolis and back)

  • Lunch + another soak before heading out?

Alright, I know that was a lot and I hopped directly in without much explanation. You probably want more details like when? how many people are we thinking? price point? etc. I haven’t thought any of that through yet. However, I’m open to anyone and everyone that wants to join the excursion. That includes YOU! Seriously. If you need to know what airport we can pick you up at let me know!

For realsies though, I’m considering any weekend mid-January to the end of February 2026. It’s always good to plan some upcoming escapes! Let me know which excursion you want and which adventures you want to experience (I’m open to suggestions not listed in case you find yourself Googling other options in each locale). I’ll tally it all up and let you know which direction we’re headed. Who’s in?!

Laura Kay Young
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