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November 7, 2025 18 mins
Episode 201: Christmas in Red Lodge, Montana Looking for a holiday getaway that feels straight out of a postcard? This week on The Family Vacationer, we’re taking you to Red Lodge, Montana, a small-town winter wonderland where Christmas magic comes alive. Red Lodge, once a bustling coal-mining town in the 1800s, is now best known as the gateway to the Beartooth Highway. But come December, it transforms into a festive haven filled with twinkling lights, family traditions, and a community spirit that makes the holidays unforgettable. Joining us is Sherry Weimer, director of the Red Lodge Chamber of Commerce, who shares why families should plan a Christmas trip to this hidden gem. In this episode, you’ll hear about:
  • The Red Lodge Christmas Stroll — a Hallmark-worthy tradition with parades, fire pits, caroling, and Santa’s grand entrance.
  • Family-friendly winter fun at Red Lodge Mountain, from skiing to skating in the town park.
  • The best cozy stops for cocoa, pastries, and kid-approved treats (don’t miss the monster ice cream sandwich!).
  • How local shops and restaurants keep the holiday spirit alive with decorated windows, late-night shopping, and tasty surprises.
  • Unique Red Lodge holiday experiences, like Santa skiing on Christmas Day.
  • Where to stay — from historic hotels to mom-and-pop motels, B&Bs, and Airbnbs.
  • Insider tips for planning your family’s first Christmas trip to Red Lodge.
If you’ve ever dreamed of celebrating Christmas in a storybook setting, Red Lodge might just be the perfect destination for your family. Plan your trip: redlodge.com
Don’t forget — we’ll be circling back to our special Episode 200 in December! Plus, stay tuned for details on Rob’s upcoming book, The Family Vacationer: A Parent’s Guide to Meaningful Travel, coming soon.
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Episode Transcript

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Speaker 1 (00:06):
This week on the Family Vacationer, we are going to
experience the magic of Red Lodge, Montana, a hidden gym
for families looking to celebrate Christmas in a small town
winter wonderland. From festive strolls and sleigh rides to cozy
coco stops and sparkling light displays, we'll explore everything that
makes Red Lodge the perfect holiday escape. Episode two hundred

(00:29):
and one starts right now. Welcome to the Family Vacationer
with Robin Tracy, your go to podcast for families on
the moon. Hey everyone, and welcome back to the Family Vacationer.

Speaker 2 (00:44):
I'm Rob and I'm Tracy. Thanks for joining us today. Now,
before we dive in, you may have noticed we're skipping
episode two hundred and Yes, we know that's unusual, but
trust us, there's a good reason why stay tuned in December,
because we'll be circling back to that special episode.

Speaker 1 (01:06):
Then that's right. County is not our specialty anyway. But
for now, we are heading west to Red Lodge, Montana.
And for those that don't know, Red Lodge has a
fascinating past. It was once a bustling coal mining town
in the late eighteen hundreds, and it grew into a
lively community that welcomed ranchers, immigrants, and adventurers. Today, Red

(01:28):
Lodge is best known as the gateway to the breathtaking
bear Tooth Highway, one of America's most scenic drives, and
while the mountains and wide open spaces make it an
outdoor lover's paradise, during December, Red Lodge transforms into something
even more special, a Christmas wonderland that feels like stepping
inside a holiday postcard.

Speaker 2 (01:50):
From its historic downtown dressed in twinkling lights, to the
community events that bring locals and visitors together, Red Lodge
knows how to do Christmas in a way that feels
both nostalgic and unforgettable. To help us paint a picture
of this festive town and share the traditions that make

(02:11):
Red Lodge shine during the holiday season, we're excited to
welcome today's guest, Cherry Weimer, director of the Red Lodge
Chamber of Commerce. Cherry, thank you so much for joining
us today.

Speaker 3 (02:24):
Thank you for having me. I'm excited to visit with you. Guys.

Speaker 1 (02:27):
We're excited to have you and talk about Red Lodge.
So let's start off for families who may not know
about Red Lodge. Can you paint a picture of what
makes the town so special during the holiday season, Well,
we do.

Speaker 3 (02:42):
A best stressed window contest, get all the stores to
dress up their windows and put some lights out, and
it's our Main street is still that quintessential authentic Western downtown.
So that in itself makes it fun just to walk
around anytime.

Speaker 2 (03:00):
What signature Christmas events or traditions does Red Lodge host
that visitors should not miss.

Speaker 3 (03:09):
It's a big one. Our Christmas Stroll, I would say,
is the best stroll anywhere. It's the first weekend in
December this year that hits on the fifth and sixth,
and it is like stepping into a Hallmark card. I say,
it's magical, and I just plan your trip around it.

(03:31):
It's fantastic. Friday afternoon, we shut down the street to cars,
walk it off so that kids and adults can just
walk out in the street. We put out fire pits
you can roast marshmallows right on the street, and then
a horse drawn wagon pull Santa up and down Main
Street to kick things off during a lighted parade. So

(03:58):
it's just the West thing you've ever seen Santa waving
to all the kids and kicking off the evening, and
then the store is stay open late and people tootle
around and shop and we have people caroling. There's different
characters on the street, like the Grinch wanders around and

(04:19):
gives the kids a hard time, and Rudolph and music's playing,
and we have nonprofits right on the street serving up
hot chocolate and stuff. So it's just a blast. It
is like you've stepped into one of those old postcards
and people are out smiling at each other and enjoying

(04:43):
an evening together.

Speaker 2 (04:44):
This is totally for me. I love Christmas. I'm loving
every minute of this. Are there any like parades or
light displays or performances that really capture the magic for
kids and families.

Speaker 3 (04:58):
Yeah, that Blade period that I talk talked about that
kind of kicks off the evening. Anybody can get into that.
That's pushing snow. So some people just dress up and
walk with a shovel, but we have a lot of
lighted entrees that are the people go all out. It's
really cool looking. So the Blade Parade is a big
part of the both evenings. It runs both nights.

Speaker 1 (05:21):
What are some other favorite winter activities that are going
on during the Christmas time, Like I don't know, sleigh rides, skiing,
any kind of festive outdoor adventures.

Speaker 3 (05:33):
Yeah, I don't have any sleigh rides, but we make
up for it with Red Ldge Mountain is our local
ski area. It's just a few miles out of town,
up the hill and it's a family friendly ski area,
big enough to offer lots of terrain and fun for
kids as well as those extreme guys. So we ski.
We love to ski and snowboard and do all that,

(05:56):
and then cross country as well. We've got some great
cross country areas with groom trails, even some you can
take your dog on, you know, get out and run
and skating. We have a great little skating rink. The
kids love it. There's fires, it's in the park and
people like fires and just have a good time hanging

(06:16):
out by the right of the rink there.

Speaker 1 (06:18):
Yeah.

Speaker 2 (06:19):
Are there any recommendations for kid friendly spots to warm up,
like a hot chocolate stop or bakeries or cozy restaurants. Yeah.

Speaker 3 (06:29):
Absolutely, cat Tell Bakery the pastries are to die for.
The adults can get a fantastic coffee and then the
kids can enjoy all kinds of drinks there, and it's
a big area, very family friendly with books and stuff
for kids to hang out and read. Pizza co is
another restaurant downtown. It's not just pizza, it's a family

(06:53):
friendly restaurant and they'd have hot chocolate and they're famous
for their unster ice cream sandwich. They take two monster
cookies and they've got delicious ice cream in there and
make a real cold dessert out of it. So it's
a fun place to hang out. And then maybe for
the teens, there's Coffee Factory roasters. You get all your

(07:17):
fancy drinks in there, and it's a little more adult
area for the teens to hang out in.

Speaker 2 (07:23):
What about holiday dishes that you recommend from any local
restaurants or anything?

Speaker 3 (07:30):
Oh gosh, I couldn't come up with anything specific. But
we're starting to be known as kind of a foody area.
There's just a real variety. Black Canyon Bistro is takes
food and gives it a Mediterranean twist, lots of Mexican
restaurants and great burgers, pizza, all that. There's just such

(07:54):
a variety and it's all in different settings from high end,
real friendly and casual.

Speaker 1 (08:00):
Well for families with younger children. Are there opportunities to
meet Santa? You said Santa makes an appearance in the parade,
but are there opportunities for the kids to meet Santa
or participate in some holiday workshops.

Speaker 3 (08:13):
Yes, I'm excited to talk about this. After the parade,
Santa goes to our Elk's Lodge, which is right on
Main Street, and goes inside and gets set up. And
then that Elk's room where he goes in is decorated
like a winter wonderland. I mean, I think there's like

(08:35):
twenty Christmas trees in there, and elves and presents and lights.
Part of the fun is just waiting in line and
seeing all the decorations until you come around the corner
and finally see Santa sitting there with missus claws and
a couple elves, just waiting to hear your story. And

(08:55):
he stays open, sits there all night of both nights,
and has a blasts talking to the kids. It's really cool.

Speaker 2 (09:04):
So how do the Red Lodge or how do Red
Lodges local businesses like the shops and the restaurants, how
do they get involved in the Christmas festivities?

Speaker 3 (09:16):
This is another fun story really unique to Red Lodge.
This is the thirty fifth year of the Christmas Stroll,
which is unbelievable because it started with the stores getting
together and deciding that they wanted to give back to
the communities and thank the locals for supporting the brick

(09:37):
and mortar, so they started this. They stay open late
and many of them hand out tasty treats and drinks
and stuff, and that's been the tradition. So everybody knows
about it and most all of them do participate, and
it's just such a neat backstory that that's how it
became what it is. We just keep adding to it.

Speaker 1 (10:00):
Sure, well, you know, anytime of year when you visit
a new destination, there are the obvious things to do.
Are there any hidden gems during the holiday season that
families might not know about but would love to experience?

Speaker 4 (10:18):
You know?

Speaker 3 (10:20):
One thing that we've enjoyed is Santa skis on Christmas Day.
So Santa is up at Red Lodge Mountain and the
kids just love it. He just skis around and talks
to them and makes appearances here and there, and it's
a special memory for those kids. And doing that on

(10:41):
Christmas Day and taking that time. It's really neat.

Speaker 2 (10:44):
Yeah, that sounds cool. When is the best time in
December to visit Red Lodge for peak Christmas activities?

Speaker 3 (10:52):
That Christmas Stroll, of course is the peak, but we
do take that next weekend and invite Santa back and
he downtown. We decorate a little area outside and during
the day and the kids can come and see him again.
So that's kind of fun. And there's other activities that
happen along with that. They do a story time at

(11:14):
the Pollard Hotel, which is our historical cornerstone hotel. A
lot of different little activities like that happen almost every
weekend through the shopping season, so come anytime.

Speaker 1 (11:29):
Well you mentioned the hotel. Are there lodging options that
you recommend for families that are visiting.

Speaker 3 (11:35):
Yes, we are really lucky. There's such a variety from
the historical Pollard to your mainstream hotels. Like we have
a quality in a lot of mom and pops, you know,
some of them are older properties, but they're really unique,
well kept, nice and clean. Once people stay there, they
come back over and over again because they love that

(11:57):
different experience. We have Airbnb, vrbo's Bed and Breakfast that's
kind of the nice part. Whatever your family's looking for
and whatever price point you need, I'll go. I've got
lots of lodging options on our website.

Speaker 2 (12:17):
What advice would you give families planning their first Christmas
trip to the Red Lodge?

Speaker 3 (12:24):
Uh, plan ahead because it is busy. I mean, that's
our one of our high seasons. So make your plans
now and then the weather, you know it is winter.
Dressed accordingly, bring layers, kind of be ready for anything,
because if it does snow on your hair, it's going
to be absolutely gorgeous. You're going to want to get
out and play, go sledding, skating, all those things. So yeah,

(12:48):
plan ahead and check on the weather, and you know,
get out and play in it.

Speaker 1 (12:54):
All right, we're going to put you on the spot.
So do you have any personal memories of Christmas and
Red Lodge that come to mind?

Speaker 3 (13:02):
Well, the big one that I go back to when
I said that Santa Ski's on Christmas Day. Our family
skis on Christmas Day. I always make up a lasagna
ahead of time the day before Christmas. We go ski
all day together and laugh and play and have fun.
And then when I get home, we throw the lazaangni

(13:22):
in the oven and just enjoy together. So it's not
your traditional situation, but we love it.

Speaker 2 (16:01):
Finally, where can listeners go online to learn more and
start planning their holiday trip to Red Lodge.

Speaker 3 (16:10):
I'm so glad you asked me that we spend a
lot of time and effort on our website, which is
www dot red Lodge dot com. I have a lodging
tab where you can find all those fabulous hotel and
lodging options. There's a webcam so you can see what's
going on downtown, and if you're confused about the dates

(16:31):
and some of the things that I mentioned going on,
there's a calendar of events and I post every little
thing that comes up and keep adding to it so
you wouldn't miss any of the fun that does come
up during that holiday. Red Lodge dot com.

Speaker 1 (16:49):
Well, Sherry, thank you so much for joining us today
and sharing all of the magical traditions that make Red
Lodge such a special destination during the holiday season. Thanks
for coming on, Thanks for having me.

Speaker 3 (17:01):
This was great.

Speaker 2 (17:02):
Thank you.

Speaker 1 (17:04):
Families. If you're looking for a place that captures the
true spirit of Christmas, this is one you'll definitely want
to consider.

Speaker 2 (17:12):
And just a quick reminder you'll want to stay tuned
for December when we circle back to episode two hundred.
We promise it'll be worth the wait.

Speaker 1 (17:23):
And before we wrap up, we'd also like to thank
you our listeners for joining us each and every week.
Be sure to subscribe so you don't miss an episode,
and check us out on Instagram or substack for more
family travel ideas and behind the scenes extras.

Speaker 2 (17:40):
Oh and one more exciting note, Rob's got a book
coming out soon. We'll share more details on that in
the coming weeks, so keep.

Speaker 1 (17:48):
An eye out and remember, folks, keep your passports and
your hearts open.

Speaker 2 (17:53):
Safe travels everyone.

Speaker 4 (18:01):
I've guardian food are the beach places and the hotel spaces,
amusement park rids and water slides, mountain ranges and seasonal changes.
I'm here to serve.

Speaker 1 (18:18):
I'm the faery vacation nerves.

Speaker 2 (18:24):
I've got in full on.

Speaker 4 (18:27):
Other beach places and hotel spaces, amusement park rats and
water slides, mountain ranges and seasonal changes.

Speaker 2 (18:40):
I'm here to serve.

Speaker 1 (18:41):
I'm the faery vacation nerves.
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