Stillwater offers so many parks, river walks, historic spots and hidden gems that a single weekend becomes an adventure. Here are local-recommended places and ideas to help you plan an outdoorsy, relaxing, and memorable couple of days.
Top Parks & Waterfront Spots
Lowell Park
This greenspace along the St. Croix River is perfect for picnics, riverside strolls, or watching the historic Lift Bridge. You’ll find grassy areas, benches, and scenic views—ideal for mornings or evening walks when the light is soft.
Pioneer Park
Perched on a bluff above downtown, this park offers excellent overlooks of Stillwater and the river. Amenities include playgrounds, large picnic shelters, walking paths, grills and restrooms—great for families or small group gatherings.
Teddy Bear Park
If you have little ones—or simply enjoy playful architecture—this award-winning park is a must. With giant teddy bear sculptures, a treehouse slide, and plenty of bold, imaginative features, it’s easy to lose track of time here.
Trails, Nature & Views
Brown’s Creek Trail & Pine Point Regional Park
Great for both hiking and biking, these areas offer trails that range from easy to more challenging. Pack water and a snack so you can stretch your time here and soak up forest, river, and bluff views.
Stillwater Stairs & Historic Flint Hill Staircases
Stillwater’s steep terrain comes with character. Five sets of old staircases connect hillsides to downtown, giving excellent viewpoints and a bonus workout. They’re worth exploring if you like your walks with a little elevation.
Lake Elmo Park Reserve
Not far out of downtown, this expansive park offers beaches, playgrounds, camping, trails (also usable in winter) and open space to relax near water. It’s one of those places where you can mix activity and rest in one outing.
Experiences & Hidden Local Favorites
Stillwater River Boats & Gondola Romantica
Take a river cruise or scenic paddle-wheel ride to see the St. Croix from a fresh angle. Ideal for relaxing afternoons or capped with sunset if you select the right time.
Art & Streetscapes
Downtown Stillwater is full of painted utility boxes, murals, and changing gallery shows—at places like ArtReach, the Public Library and Union Art Alley. A casual walk + a cup of coffee = a lovely mid-morning or early afternoon.
Treats Trail & Main Street Shops
Indulge your sweet tooth by following the Treats Trail, which takes you through several candy shops, frozen-treat spots and local dessert joints along the river. Couple that with window-shopping on Main Street for an easy afternoon diversion.
Weekend Itinerary Suggestions
Morning: Start in the quieter hours with a walk along Lowell Park or Brown’s Creek Trail.
Midday: Head toward Pioneer Park for a picnic and perhaps a bite in town. Follow up with some browsing through local shops or stop for an ice cream via the Treats Trail.
Afternoon: If you enjoy art or history, catch a gallery or museum. Otherwise, lake or river time via one of the boat tours makes for a relaxing pace.
Evening: Grab dinner downtown overlooking the water, then wind down with quiet time at Teddy Bear Park or let the sunset glow from one of the hillside stairways.