Skip to content

A Stillwater Staycation at Hotel Crosby

Disclosure Policy: Some links are affiliate links meaning I may make a small commission at no cost to you. I appreciate your support!

Stillwater Staycation

Stillwater is one of the best small towns in America and our winter Stillwater Staycation at Hotel Crosby has become one of my favorite Minnesota travel experiences to date! While I’d recommend visiting in any season, Stillwater completely transforms into the most charming winter wonderland destination.  From ice skating to nightly light shows to snowshoeing amongst tall towering pines along the Saint Croix River, Stillwater is incredibly idyllic.  Read on for the top things to do in Stillwater on a winter staycation!

Note: Discover Stillwater hosted our visit.  The itinerary was planned by me and as always opinions are my own.

Where to Stay:

Hotel Crosby is a newer boutique hotel located right on Main Street in Stillwater.  The rooms are beautifully decorated with fun details, the lobby is very inviting with a big fireplace as you walk in, there’s a rooftop hot tub and the popular Matchstick restaurant and bar is located right in the lobby! We stayed in a beautiful king suite and found it so comfortable. 

Our whole stay from check-in to check-out was great and we especially enjoyed using the rooftop hot tub in the middle of winter under the lights. There’s a free parking ramp right behind Hotel Crosby for hotel guests too.  Highly recommend booking a stay at Hotel Crosby

We’ve also stayed at Lora Hotel which is another great option.  Note – these are affiliate links. I appreciate your support!   


We visited mid-week when Stillwater is generally less busy.  Rates are usually lower mid-week at hotels too.  Just check that restaurants that you want to visit are open since some are closed Monday-Wednesday.

Top Things to Do

Walk through the Ice Palace Maze

The Ice Palace Maze has become one of the coolest attractions in Stillwater! The maze is completely made out of ice and at night time the lights come on making it even more beautiful. The ice slide at the end is so fun to go down too! Entrance times are limited due to COVID. In addition to the maze, there are firepits, an ice bar and hot coco plus snacks available. Note – the warm weather has caused the maze to close early. Put this on your list for next year!

Ice Skate at the free riverside rink

There’s a free ice-skating rink in front of the Water Street Inn overlooking the river. I loved the views of the bridge while we got in a little exercise!  Just bring your own skates and there are tables set up for changing into them.

Stroll through the Nightly Lights

Through March, there are beautiful nightly lights that lead to the Lift Bridge.  Make sure to check them out and perhaps take a stroll across the bridge to Wisconsin and back. Any border crossing feels exciting these days!  The lights are on from 5-10PM daily through March.

Go on a snowshoe adventure with Diro Outdoors

A true highlight of our visit was snowshoeing at Arcola Bluffs Day Use area, thanks to a fabulous snowshoe package from Diro Outdoors.   They packed snowshoes, snacks, waters, maps, a waterproof blanket and a bag to carry it all and had it waiting at our hotel for a 7AM sunrise hike.  It was incredibly convenient to grab the pack from the hotel lobby and head out for an adventure!

If we had more time, I would have loved snowshoeing at Willow River State Park but we had a great time hiking through the Arcola Bluffs area.  Our adventure took about an hour round trip.  When we were done, we dropped the snowshoes back off at the front desk of our hotel for Diro Outdoors to pick up – so easy!  In addition to snowshoe packs, Diro Outdoors rents tons of gear from bikes to camping. Their hot tent is next on my list for a winter adventure!

Throw Axes at The Lumberjack

Stillwater is the perfect place to try your hand at axe throwing!  The Lumberjack is a gorgeous venue where you can reserve time to throw axes, eat dinner and have a drink.  They often have live music too.  Make your reservation in advance because the axe throwing lanes do fill up!   

Dine at many of the great establishments

Stillwater has so many great restaurants it’s always hard to narrow it down for our trips! On this visit, we had a few wonderful dining experiences all on the main street:

Lolito Cantina

Lolito has delicious Mexican fare and I’d highly recommend the tacos, plantains and avocado salsa with chips. The dining space is beautifully decorated too.  We took our lunch to-go to enjoy in our hotel room but in the future I’d love to dine in!

The Lumberjack

After throwing axes, we enjoyed a delicious meal of grown-up grilled cheese, a buffalo chicken sandwich and cheesecake for dessert at The Lumberjack.  The food is incredible and tasted so fresh.  Even if you’re not planning to throw axes, I’d still recommend dining or having drinks here!

Oasis Cafe

One of the most classic food stops in Stillwater is Oasis Café.  It originally opened in 1957 and is set in the bluffs right as you come in to Stillwater.  The diner style food is perfect for any meal but I particularly love it for breakfast! The omelets and banana bread French toast are two of my favorites!

Grab a Boba tea at Mai Little Cakes

Located in the heart of Stillwater is Mai Little Cakes, a delicious cake, rolled ice cream and boba tea shop.  Opened by Cake Wars winner, Mai, this shop is a wonderful addition to the Stillwater area. I’m a big fan of boba tea so we enjoyed a classic Thai Milk tea.  We also bought a boba bomb to enjoy a milk tea at home later. Everything sounds delicious and I can’t wait to come back.    

Shop Local

There are so many great shops in Stillwater so make sure to add time to peruse them! One of my new favorites is Toxy Free.  It’s a beautiful shop curated with special items that are all toxic-free.  I would love to decorate my whole home with items from here! For more great shop ideas for your trip, click here.

Grab a cocktail kit to go from Forge & Foundry

A new craft distillery located right on the main street in Stillwater, Forge & Foundry is a must visit! In warmer weather, you can enjoy cocktails on the rooftop overlooking the river.  Otherwise, the tasting room is a beautiful space to relax in too.  We opted to pick up a cocktail kit to go so we could make a cocktail at the rooftop hot tub at our hotel!

Enjoy the hot tub at Hotel Crosby

Make sure to enjoy the hot tub if you’re staying at Hotel Crosby! It’s a huge perk of planning your Stillwater staycation at Hotel Crosby. We enjoyed winding down our busy day of exploring here.  We also brought our cocktails from the kits at Forge & Foundry to enjoy on the rooftop. Perfect way to toast a fabulous visit!

Ready to plan your Stillwater Staycation at Hotel Crosby?! For more Stillwater ideas, read about our early fall visit here.

Even more Minnesota travel ideas can be found here.

Happy Planning!

Posted in

You may also enjoy...

Scroll To Top