The Ultimate Weekend Getaway in Stillwater, Minnesota

Whether you are looking to take a romantic getaway with your significant other, a fun girls weekend, or simply a relaxing staycation for yourself in Minnesota, Stillwater is a great option! It is 40 minutes outside of the Minneapolis–Saint Paul metropolitan area and located on the beautiful west bank of the St. Croix River. In this guide, we will share tips on where to stay, where to eat, and what to do while in Stillwater.

We partnered with Discover Stillwater to come up with the perfect itinerary for a two-day trip to Stillwater and want to share it with you! Read to the end to find additional thrifty tips and the printable itinerary.

Where to Stay 

Stillwater is situated on the St. Croix River, so there is no place with a bad view! For lodging in Stillwater, there is plenty of bed & breakfasts and hotels to choose from, in addition to house and loft rentals. Discover Stillwater has a great chart of all of the lodging options with the amenity breakdown. We highly recommend staying in the heart of downtown on Main Street.

We stayed at a downtown loft on Main Street hosted by Stillwater Airbnbs. The loft was a cute and charming one-bedroom, two-bathroom apartment with a rooftop deck (that was our favorite thing!) Parking was accessible, and we were able to walk everywhere! To get from one end of Main Street to the other end, it was only a 10 to 15-minute walk.

Where to Eat

One of our favorite things to do on vacation is eating and drinking! We love basking in the sun at a nice outdoor patio or cafe, taking in the scenery at a beautiful rooftop restaurant, or casually drinking at a local bar or pub. Stillwater has all of these options! Discover Stillwater makes it easy to find a dining option by listing all of the places on the Dining and Nightlife section of their website. Here are some of our favorites we visited:

-Inside Hotel Crosby on Main Street is a restaurant called MatchStick. Monday-Friday, from 3 to 5 pm, they have a great Happy Hour for 1/2 off beer and cocktails, along with special-priced apps.

-Mai’s Little Cakes: an Asian-owned, woman-owned bakery with the cutest desserts and even cuter atmosphere. Mai is the owner and pastry chef who won Cake Wars on the Food Network. Stop in to meet a celebrity chef! (UPDATE: This store has since closed)

What to Do 

From live music to special events, there is always something to do in Stillwater. Visit Discover Stillwater’s events calendar for the most up-to-date list of fun activities. We would also recommend the below activities while you’re in Stillwater:

-Have lunch or dinner on the Stillwater River Boat Cruise while overlooking the scenic St. Croix River.

-Enjoy a gondola ride on the St. Croix River with John from Gondola Romantica. Bringing the romance of Venice to Stillwater, Minnesota, this is a wonderful and relaxing experience to see Stillwater from the river’s perspective.

–#ShopSmall and check out all of the independently-owned businesses and boutiques on Main Street. There are 50 unique shops downtown Stillwater, and one of the store managers, Chris, was featured in our Minnesota Gift Guide.

-Visit Kelli & Paul Kaufer at Smith + Trade Mercantile. This general store has so many beautiful handcrafted items made by Minnesotans and Wisconsinites. You’ll be inspired by the work that you’ll want to take a craft class yourself. Good thing Smith + Trade offer all sorts of classes!

-Plan a wine and beer tour! Grab your group and rent a limo or trolley to take you to all of the wineries and breweries in Stillwater.

Two Day Example Itinerary

Day 1 

• Arrive at downtown Stillwater and settle into your hotel or Stillwater Airbnbs near Main Street.
• Shop along Main Street and check out all of the local boutiques. 
• Grab a bite to eat at Quick Fire Pizza along Main Street.
• Take a stroll along the Stillwater Bridge for a beautiful view of the St. Croix River.
• Grab Happy Hour drinks and food inside Hotel Crosby at MatchStick (HH from 3-5pm).
• End the day with a visit to Leo’s Grill & Malt Shop for their infamous milkshakes.

Day 2 

• Coffee and breakfast at Made Cafe. 
• Head to the dock for a Stillwater River Boat Cruise or Gondola Romantica ride along the St. Croix River.
• Enjoy a Wine Tasting at Rustic Roots Winery. 
• Dinner and drinks at Brick & Bourbon – make sure to grab a seat on their outdoor patio!
• Don’t leave without stopping at the 1932 CandyLand Shop for assorted popcorn and old-fashioned candies.

We hope you enjoy your Stillwater getaway!! Make sure to check out some of our other Minnesota blog posts for more local adventures.