Make a Trip of It

Montana (and the American West in general) is absolutely stunning in early June, and many guests are turning the wedding into a little holiday. There are so many gorgeous towns, national parks, and mountain drives nearby, so here are a few easy itinerary ideas depending on how much time you have. Nothing here is meant to be overwhelming — just inspiration for a beautiful few days.

2 DAYS

NYC, LA + Montana

Perfect for anyone making a slightly longer holiday out of the trip.

New York
Spend two days in NYC: a museum, a good dinner, a cocktail or two, and then take the direct flight to Bozeman for the wedding.

Los Angeles
LA is also a great two-day option, with a couple of direct flights to Bozeman. Enjoy a relaxed beach day, some shopping, great food, and then an easy, straight shot into Montana.

You can always add Big Sky, Yellowstone, or Paradise Valley afterward.

5 DAYS

Bozeman → Yellowstone → Jackson Hole

For anyone who wants the “classic West” — national parks, wildlife, and a chic little town to end in.

Day 1 — Arrive in Bozeman
Settle in, wander Main Street, grab dinner, and reset.

Day 2 — Yellowstone
Pick up a rental car and head into the park. The North and West entrances are both easy drives. Spend the day doing a mix of geysers, bison spotting, and scenic stops.

Day 3 — Yellowstone → Jackson Hole
Continue through the park and arrive in Jackson Hole by late afternoon.
Where to stay: Anvil Hotel, Hotel Jackson, Caldera House.

Days 4–5 — Jackson Hole
Bike to a lake, explore Grand Teton National Park, or simply enjoy the restaurants and galleries. And definitely visit the Cowboy Bar — it’s iconic.
From here, you can fly home or drive back up to Montana for the wedding.

7 DAYS

A Relaxed Montana Loop

A great way to see a mix of charming towns and knockout scenery without rushing.

Day 1 — Bozeman
Sleep off the travel, grab a coffee, wander the shops.

Day 2 — Red Lodge
Drive to Red Lodge, a sweet little Western town with great shops and restaurants.
Must-book dinner: Piccola Cucina at Ox Pasture — an upscale, Italian-forward spot that’s part of the same group behind several chic NYC locations and even Ibiza. Such a fun surprise in a tiny Montana mountain town.

Day 3 — Beartooth Pass → Yellowstone or Cody
Take the Beartooth Highway — genuinely one of the most beautiful drives in America — either dipping into Yellowstone or continuing on to Cody, WY.
If you prefer a slightly shorter loop: you can skip Big Sky and drive straight back north via Paradise Valley, which is just as beautiful and a bit more direct.

Days 4–5 — Big Sky (optional)
If you continue the full loop, spend two nights in Big Sky.
Where to stay: Lone Mountain Ranch or Montage Big Sky.
Think scenic lifts, hiking, spa time, and cozy candlelit dinners.

Days 6–7 — Paradise Valley / Livingston
Whether you arrive here directly from Cody/Red Lodge or after Big Sky, Paradise Valley is the perfect slow finish: hot springs, river views, fly-fishing, and sometimes live music at Pine Creek Lodge. Then an easy drive to CMR for the wedding.

Whitefish & Glacier National Park

If you’re drawn to alpine lakes, dramatic peaks, and a cooler, greener landscape.

Day 1 — Bozeman
Ease in.

Day 2 — Drive to Whitefish
A gorgeous 5–6 hour drive north.

Days 3–5 — Glacier National Park
Going-to-the-Sun Road, Lake McDonald, short hikes, and evening drinks in Whitefish. It’s incredibly pretty and feels a bit different from the rest of Montana.

Days 6–7 — Back toward Bozeman / Livingston
Head south to be closer to the wedding.

10 DAYS

The Big Western Road Trip (Denver → Montana)

For the true road-trip people who want to see everything.

Option A — Desert + National Parks
Denver → Colorado Springs → Santa Fe → Flagstaff → Zion → Park City → Jackson → Montana.

Option B — Mountain Towns + Ranch Country
Denver → Steamboat → tiny Encampment, WY → Jackson → Big Sky → Bozeman / Livingston → CMR.

Both versions are beautiful — it just depends if you want more red rock or more mountains.

Other Options + Weather Details

Under Canvas (Glamping)

Yes! Under Canvas North Yellowstone – Paradise Valley (the one closest to our wedding) will be open in June and is a lovely option for a night or two of luxury glamping as part of a Yellowstone loop.

A Note on June Weather

Montana in early June is sunny, warm, and wildly beautiful, but it’s still the mountains — so weather can change very quickly.
Here’s what to expect:

  • Highs: 65–80°F (18–27°C)

  • Lows: 40–50°F (4–10°C), especially in the evenings

  • Mornings: crisp and bright

  • Afternoons: warm with the occasional quick mountain shower

  • Evenings: cool enough for a sweater or light jacket

  • And yes — very occasionally, a quick mountain snow flurry (usually only at higher elevations, but it can happen!)

Layers are your best friend: linen or cotton during the day, then a knit or jacket for dinners and sunset.

If you want any extra help planning or have questions about routes, hotels, or timing, please feel free to reach out to us — we’re more than happy to help point you in the right direction.

And if you already know where you’re thinking of going, let us know! We can gather more suggestions, hidden gems, and tips tailored to your itinerary.