Stillwater suits a weekend better than almost anywhere in the Twin Cities region. The downtown is compact, the main experiences are within a few minutes of each other, and the valley beyond offers a choice of nature, art and heritage for a second day. This itinerary assumes you arrive on Friday evening or early on Saturday and leave on Sunday, and it can be shortened to a long day trip.
Friday evening: settle in
Check in to your hotel, then walk down to the riverfront to look at the lift bridge. Have dinner in town. Hotel restaurants such as MatchStick at Hotel Crosby, Feller at the Lora and Charlie’s at Water Street Inn are all reasonable choices, and the Lowell Inn’s dining rooms are a classic for a special evening. Book ahead on weekends.
Saturday morning: trolley and Main Street
Take the Stillwater Historic Trolley Tour first thing, when the narration is fresh and you can plan the rest of the day around what you hear. The tour lasts about 45 minutes. Afterwards, walk down to Main Street and spend the rest of the morning in the independent shops, bookstores and antique stores, with a break at the soda shop.
Saturday afternoon: on the water
A two-hour paddlewheel cruise is the obvious choice, with the lift bridge passing overhead and the bluffs on either side. Reserve in advance because cruises require reservations and run from early May to mid-October. Outside the cruise season, substitute a visit to the Warden’s House Museum, which has guided tours from Thursday to Sunday.
Saturday evening: a drink and a story
Have dinner, then choose between a cocktail at one of the downtown bars, a visit to the speakeasy or, in October, the Rivertown Terror haunted trolley tour. For a quieter night, walk the riverfront after dark.
Sunday morning, option A: the northern valley
Drive north to Interstate State Park at Taylors Falls to see the Dalles, the glacial potholes and the cliff-top trails, then visit Franconia Sculpture Park, which is free and open daily. If you like heritage, add the Gammelgården Museum in Scandia on a tour day.
Sunday morning, option B: orchards and wine
In autumn, head to Aamodt’s Apple Farm and Saint Croix Vineyards for pick-your-own apples, hayrides and cider. Anyone celebrating something might add a hot air balloon flight from the same property, weather permitting.
Sunday afternoon: one last stroll
Return to downtown for a final lunch and a walk by the river before the drive home. If you have time, visit the courthouse on the hill for the view over the rooftops.
Where to stay
Hotel Crosby and the Lora are the stylish downtown choices, Water Street Inn is the classic riverside inn and the Rivertown Inn and James Mulvey Carriage House Inn are cosy, romantic options. Reserve early, because autumn weekends sell out.
If you only have one day
Do the trolley, Main Street, lunch and the cruise, and skip the valley. Add the second day when you can, because the northern valley is the part of the region that most visitors miss.
Rainy-day swaps
If the weather turns, trade the cruise for the Warden’s House Museum, a long lunch and an afternoon in the bookstores and antique shops. The hotel spas at Hotel Crosby are another good wet-weather idea, and the Murder Mystery Detective Experience can be played between showers if you have a waterproof layer. Indoor options are limited in a small town, so build one or two into the plan.
Making it romantic
For couples, book a dinner sailing on a weekend, a table in the Matterhorn Dining Room for fondue, or a room with a fireplace or jetted tub at one of the inns. A hot air balloon flight from the orchard property is the big gesture, if weather and the operator allow. Reserve everything early, and mention an anniversary when you book so the staff can help.
Travelling with children
Children enjoy the trolley, the boats and the orchard far more than the museums, so weight the plan towards those. Pick your own apples in autumn, watch for the lift bridge from the riverfront and let them choose a treat at the soda shop. Keep the northern valley for a second day, and build in downtime, because a small town tires young legs on its steep streets.
Fitting in the drive
The trip from the Twin Cities takes roughly forty minutes outside rush hour, so a Friday evening arrival works if you leave a little before the traffic builds. On Sunday, leave before mid-afternoon to avoid the return crush on autumn weekends.